- Cytotoxicity and Antibacterial Evaluation of O-Alkylated/Acylated Quinazolin-4-one Schiff Bases
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A series of quinazolin-4-one Schiff bases were synthesized and tested in vitro for their cytotoxicity against two cancerous cell lines (MCF-7, Caco-2) and a human embryonic cell line (HEK-293) including their antibacterial evaluation against two Gram-positive and four Gram-negative bacterial strains. Most of the quinazoline-Schiff bases exhibited potent cytotoxicity against Caco-2. 3-[(Z)-({4-[(But-2-yn-1-yl)oxy]phenyl}methylidene)amino]-2-methylquinazolin-4(3H)-one (6f) with the O-butyne functional group displayed three-fold higher cytotoxic activity (IC50=376.8 μM) as compared to 5-fluorouracil (5-FU; IC50=1086.1 μM). However, all compounds were found to be toxic to HEK-293, except for 3-[(Z)-({4-[(2,4-difluorophenyl)methoxy]phenyl}methylidene)amino]-2-methylquinazolin-4(3H)-one (6h) that showed ~three-fold lower toxicity and higher selectivity index than 5-FU. Structure–activity relationship (SAR) analysis revealed that O-alkylation generally increased the anticancer activity and selectivity of quinazoline-4-one Schiff bases toward Caco-2 cells. The fluorinated Schiff-base generally exhibited even more significant cytotoxic activity compared to their chlorine analogs. Surprisingly, none of the quinazoline-4-one Schiff bases displayed encouraging antibacterial activity against the bacterial strains investigated. Most of the compounds were predicted to show compliance with the Lipinski parameters and ADMET profiles, indicating their drug-like properties.
- Manhas, Neha,Singh, Parvesh,Mocktar, Chunderika,Singh, Moganavelli,Koorbanally, Neil
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- La(III) complex involving the O,N-donor environment of quinazoline-4(3H)- one Schiff's base and their antimicrobial attributes against methicillin-resistant Staphylococcus aureus (MRSA)
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The incidence of methicillin-resistant Staphylococcus aureus increased during the past few decades, so there is an urgent need of new antimicrobial agents if public health is concerned. Though the Schiff's bases and La(III) complex have enormous biological activity, but less attention was given in their synthesis. In the present investigation, we synthesized a new (E)-3-((2-hydroxynaphthalen-1-yl) methyleneamino)-2-methylquinazoline-4(3H)-one HNMAMQ Schiff's base by the condensation of 3-(2-aminophenyl) quinazolin-2-methyl-4(3H)-one and 2-hydroxy-1-naphthaldehyde. The Schiff's base HNMAMQ and its La(III) complex were characterized by elemental analyses, IR, NMR, mass spectra, and thermal studies. The newly synthesized Schiff's base HNMAMQ and its La(III) complex were evaluated for their antimicrobial activity against methicillin-resistant Staphylococcus aureus isolated from the Gulbarga region in India. The Schiff's base HNMAMQ and its La(III) complex showed good antimicrobial activity and thus represents a potential new drug of choice.
- Siddappa,Mane, Sunilkumar B.,Manikprabhu, Deene
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- N-amination of 4-pyrimidones by mesitylenesulfonyl hydroxylamine
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The 3-amino derivatives are formed exclusively during the amination of the anions of 6-methyl-4-pyrimidones and 2-methyl-4-quinazolone by mesitylenesulfonyl hydroxylamine.
- Ivanov,Tsyrenov,Antonov,Lobanov,Potekhin
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- 2-{2"-carbomyl-5"-[3′-amino-2′-methylmono/ dihalosubstituted quinazolin-4′(3'h)-onomethylene]- 1",3",4"-oxadiazol-2"-yl}-4,5-dihydroimidazolines as potential antihypertensive agents
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Twelve new 2- {2"-carbomyl - 5" - [3′-amino-2′ - methylmono / dihalosubstituted quinazolin- 4′ (3'H) - onomethylene] - 1",3",4" - oxadiazol-2"-yl} -4, 5- dihydroimidazolines were prepared and evaluated for their cardiovascular activity. The most active compound of this series is 2-{2"- carbomyl-5"-[3′-amino-2′-methyl-6-bromoquinazolin-4′(3'H)-onomethylene]-",3",4"-oxadiazol-2"- yl}-4,5-dihydroimidazolines i.e. compound VIc.
- Tyagi, Mirdula
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- Synthesis of Some Quinazolinone Derivatives Functionalized with N-3 Heterocyclic Side Chain
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A number of quinazolinone derivatives substituted at position-3 are prepared from 3, 1-benzoxazinone. Thus, treatment of 3, 1-benzoxazinon with cyanoacetohydrazide or thionocarbohydrazide gave the quinazolinone derivatives. The quinazolinones have been utilized as synthon for new pyridinone, azete, thiazole, thiazolidinone, thosemicarbazide, and thiosemicarbazone derivatives. The structures of the synthesized compounds were established on the basis of IR, 1HNMR, mass spectral data, and elemental analyses.
- Youssef, Ahmed S. A.,Hemdan, Magdy M.,El-Mariah, Fatma A.,Hashem, Heba E.
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- Synthesis, biological evaluation, and in silico study of novel library sulfonates containing quinazolin-4(3H)-one derivatives as potential aldose reductase inhibitors
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A series of novel sulfonates containing quinazolin-4(3H)-one ring derivatives was designed to inhibit aldose reductase (ALR2, EC 1.1.1.21). Novel quinazolinone derivatives (1–21) were synthesized from the reaction of sulfonated aldehydes with 3-amino-2-alkylquinazolin-4(3H)-ones in glacial acetic acid with good yields (85%–94%). The structures of the novel molecules were characterized using IR, 1H-NMR, 13C-NMR, and HRMS. All the novel quinazolinones (1–21) demonstrated nanomolar levels of inhibitory activity against ALR2 (KIs are in the range of 101.50–2066.00 nM). Besides, 4-[(2-isopropyl-4-oxoquinazolin-3[4H]-ylimino)methyl]phenyl benzenesulfonate (15) showed higher inhibitor activity inhibited ALR2 up to 7.7-fold compared to epalrestat, a standard inhibitor. Binding interactions between ALR2 and quinazolinones have been investigated using Schr?dinger Small-Molecule Drug Discovery Suite 2021–1, reported possible inhibitor-ALR2 interactions. Both in vitro and in silico study results suggest that these quinazolin-4(3H)-one ring derivatives (1–21) require further molecular modification to improve their drug nominee potency as an ALR2 inhibitor.
- Tokal?, Feyzi Sinan,Demir, Yeliz,Demircio?lu, ?brahim Hakk?,Türke?, Cüneyt,Kalay, Erbay,?endil, K?v?lc?m,Beydemir, ?ükrü
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- Imidazolium chloride as an additive for synthesis of 4(3H)-quinazolinones using anthranilamides and DMF derivatives
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Imidazolium chloride as an environmentally benign additive efficiently facilitates construction of 4(3H)-quinazolinones using anthranilamides and DMF derivatives. A series of 4(3H)-quinazolinones were prepared in moderate to excellent yields without conventional oxidants, metal catalysts and corrosive acids or other additives.
- Dai, Zeshu,Li, Dan,Li, Zhiyao,Liu, Heng,Luo, Wen,Shang, Suqin,Tian, Qingqiang,Wang, Shuqi,Wang, Xuetong,Wang, Yin,Wu, Huili,Xiao, Xin,Yuan, Jianyong,Zhou, Shangjun
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- Synthesis, anticorrosion, antibacterial, and antifungal activity of new amphiphilic compounds possessing quinazolin-4(3H)-one scaffold
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For the first time, quinazolin-4(3H)-one-based cationic surfactants were prepared and fully characterized by IR and NMR spectroscopic techniques and elemental analysis. Some of their physicochemical properties, such as density, critical micelle concentrat
- ?ztürk, S.,Okay, S.,Y?ld?r?m, A.
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p. 2205 - 2214
(2020/12/09)
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- Synthesis and evaluation of anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities of some 3H-quinazolin-4-one derivatives
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Some new 3H-quinazolin-4-one derivatives were synthesised and screened for anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities. Compound 15d was more potent in reducing the cell viabilities of HT-29 and SW620 cells lines to 38%, 36.7%, compared to 5-FU which demonstrated cell viabilities of 65.9 and 42.7% respectively. The IC50 values of 15d were ~20?μg/ml. Assessment of apoptotic activity revealed that 15d decreased the cell viability by down regulating Bcl2 and BclxL. Moreover, compounds, 8j, 8d/15a/15e, 5b, and 8f displayed lowered IC50 values than oleanolic acid against proinflammatory isoforms of hGV, hG-X, NmPLA2, and AmPLA2. In addition, 8d, 8h, 8j, 15a, 15b, 15e, and 15f showed better anti-α-amylase than quercetin, whereas 8g, 8h, and 8i showed higher anti-α-glucosidase activity than allopurinol. Thus, these compounds can be considered as potential antidiabetic agents. Finally, none of the compounds showed higher antiproteases or xanthine oxidase activities than the used reference drugs.
- El-Sayed, Nahed N. E.,Almaneai, Norah M.,Ben Bacha, Abir,Al-Obeed, Omar,Ahmad, Rehan,Abdulla, Maha,Alafeefy, Ahmed M.
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p. 672 - 683
(2019/04/02)
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- Quinazolin-4(3H)-ones and 5,6-dihydropyrimidin-4(3H)-ones from β-aminoamides and orthoesters
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Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12–24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110?C for 12–72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, 1H-NMR, 13C-NMR, and HRMS.
- Gavin, Joshua T.,Annor-Gyamfi, Joel K.,Bunce, Richard A.
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- Quinazolinone platinum metal complexes: In silico design, synthesis and evaluation of anticancer activity
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Dihydrofolate reductase (DHFR) has been explored as a target for the development of agents for wide variety of human diseases, including cancer, autoimmune and infectious diseases. Several metal complexes are being used in management of cancer. The square planar Pt(II) complex, cis PtCl2(NH3)2 turned out to be even more effective at forcing filamentous growth. Cisplatin is an inorganic heavy metal complex that has activity similar to cell-cycle-phase-nonspecific alkylating agents such as cyclophosphamide and some other Ni and Cu metal complexes. It produces intrastrand DNA cross-link and form DNA adducts, thus inhibiting the synthesis of DNA, RNA and proteins preferentially. in silico Screening of platinum metal complexes was performed by Vlife MDS 4.3 software. In this procedure, selection of molecule, selection of PDB, optimization of PDB and docking of molecules was carried out. Synthesis of metal complexes was done by multi component reaction method. Platinum metal complexes of quinazolinone Schiff bases prioritized by in silico studies were characterized by IR, TLC, NMR, XRD, FESEM and some physico-chemical parameters. Prioritized molecules were further evaluated by in vitro anticancer cell line assay on ten cell lines with adriamycin as standard. The results showed that the platinum metal complexes of qunazolinone Schiff bases can be potential anticancer agents through DHFR inhibitory mechanism.
- Sawant, Sanjay D.,Sahu, Megha,Nerkar, Amit G.
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p. 2164 - 2170
(2018/09/10)
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- Synthesis and Evaluation of Novel [1,2,4]Triazolo[1,5-c]quinazoline Derivatives as Antibacterial Agents
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A series of new 2-aryl-5-methyl-[1,2,4]triazolo[1,5-c]quinazoline derivatives (5a–5g) have been synthesized by the reaction of 3-amino-2-methylquinazolin-4-(3H)-one (3) with aromatic nitriles in potassium tert-butoxide under reflux conditions. 3-Amino-2-methylquinazolin-4-(3H)-one (3) was synthesized by the reaction 2-methyl-4H-benzo[d][1,3]oxazin-4-one (2) with hydrazine hydrate. The chemical structure of products was confirmed by IR, 1H, 13C NMR and elemental analysis. These compounds were screened for antibacterial [Staphylococcus aureus (ATCC 25923), Bacillus cereus (ATCC 11778), Micrococcus luteus (ATCC 9341), Escherichia coli (ATCC 25922), and Pseudomonas aeruginosa (ATCC 27853)] activities, using the zone inhibition method.
- Zeydi, Masoud Mohammadi,Montazeri, Naser,Fouladi, Mahdi
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p. 3549 - 3553
(2017/11/21)
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- Expeditious synthesis and spectroscopic characterization of 2-methyl-3-substituted-quinazolin-4(3H)-one derivatives
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Quinazoline and quinazolinone derivatives are well-known bioactive heterocycles owing to their therapeutic diversity and extensive medicinal application in drug design and pharmaceutics. A series of 2-methyl-3-substituted quinazolin-4(3H)-one derivatives 8a-q was herein synthesized from synthetic conversion of anthranilic acid to 2-methyl-4H-3,1-benzoxazi-4-one, 7 which was subsequently transformed to the targeted 2,3-disubstituted quinazolin-4(3H)-one derivatives 8a-q by reacting with some notable amino-containing moieties via an ameliorable pathway. The catalyst-free synthesis was successful achieved by careful reaction optimization study using solvent choice and reaction temperature variability as key parameters. The chemical structures of the synthesized compounds were confirmed by IR, UV, 1H-NMR, 13C-NMR and DEPT-135 as well as analytical data.
- Ajani, Olayinka O.,Audu, Oluwatosin Y.,Germann, Markus W.,Bello, Babatunde L.
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p. 562 - 574
(2017/05/26)
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- Synthesis and antimicrobial assessments of some quinazolines and their annulated systems
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The syntheses of some new derivatives of quinazoline and their annulated derivatives are described in this work. Investigation of antimicrobial activity of the new products was evaluated using agar well diffusion methods with determination of minimal inhi
- Hemdan, Magdy M.,Youssef, Ahmed S.A.,El-Mariah, Fatma A.,Hashem, Heba E.
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p. 106 - 111
(2017/03/15)
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- Synthesis, 3D pharmacophore, QSAR and docking studies of novel quinazoline derivatives with nitric oxide release moiety as preferential COX-2 inhibitors
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Four novel series of 1-substituted-3-(2-methyl-4-oxo-4H-quinazolin-3-yl) urea and/or thiourea IIIa-c, 4-substituted-N-(2-methyl-4-oxo-4H-quinazolin-3-yl) benzene sulfonamide VIa-c and their NO-hybrid molecules as nitrate esters Va-c and VIIIa-c have been
- Farag, Doaa Boshra,Farag, Nahla A.,Esmat, Ahmed,Abuelezz, Sally A.,Abdel-Salam Ibrahim, Eman,Abou El Ella, Dalal A.
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p. 283 - 299
(2015/03/30)
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- Design and synthesis of quinazolinone tagged acridones as cytotoxic agents and their effects on EGFR tyrosine kinase
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In a quest for finding potent cytotoxic molecules, we have designed and synthesized a new scaffold by tagging quinazolinones with an acridone moiety. The new acridone-4-carboximide derivatives were evaluated for their cytotoxic potentials against the MCF7 breast cancer cell line and three colon cancer cell lines (LS174T, SW1398, and WiDr). Compound 26 showed relatively potent cytotoxic activity among the derivatives, against all the cell lines tested. Mechanistic studies for the selected derivatives 7, 8, 16, 17, 25, and 26 were conducted through in vitro EGFR tyrosine kinase inhibition studies. The results indicate that compound 26 has a better EGFR tyrosine kinase inhibitory profile. The in vitro EGFR inhibition data was correlated with the cytotoxic properties, and molecular docking studies were performed with regard to the receptor autophosphorylation sites of the protein kinase domain of the EGFR.
- Babu, Yarlagadda Rajesh,Bhagavanraju, Mantripragada,Reddy, Gade Deepak,Peters, Godefridus J.,Prasad, Velivela V. S. Rajendra
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p. 624 - 634
(2014/11/08)
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- Dihydrofolate reductase inhibitors: Synthesis, characterization and biological evaluation of some novel 2,3-disubstituted quinazolinones
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A series of some novel dihydrofolate reductase inhibitors (DHFR) of 2,3-disubstituted quinazolinone derivatives were synthesized by condensing benzoxazone derivatives with compounds containing primary amino group. The chemical structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, Mass spectral data and elemental analysis. The enzyme inhibitory activities were studied by using GLIDE 4.5 module. In vitro cytotoxic activity of the synthesized compounds was evaluated by MTT assay method. Compounds 3g and 5a exhibited good hydrogen bond interactions with the amino acid residue of DHFR and also showed significant cytotoxic activity.
- Hemalatha,Kumar, M. Suresh,Girija
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- Design, synthesis and potential 6 Hz psychomotor seizure test activity of some novel 2-(substituted)-3-{[substituted]amino}quinazolin-4(3H)-one
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Thirty new 2-(substituted)-3-{[substituted]amino}quinazolin-4(3H)-one were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity of the titled compounds was assessed using the 6 Hz psychomotor seizure test. The most active compound of the series was 3-({(E)-[3-(4-chloro-3-methylphenoxy)phenyl]methylidene}amino) -2-phenylquinazolin-4(3H)-one PhQZ 7, which showed 100% protection (4/4, 0.5 h) and 75% protection (3/4, 0.25 h) at a dose of 100 mg/kg in mice. A computational study was carried out for calculation of pharmacophore pattern and prediction of pharmacokinetic properties. Titled compounds have also exhibited good binding properties with epilepsy molecular targets such as glutamate, GABA (A) delta and GABA (A) alpha-1 receptors, in Lamarckian genetic algorithm based flexible docking studies.
- Kumar, Praveen,Shrivastava, Birendra,Pandeya, Surendra N.,Stables, James P.
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p. 1006 - 1018
(2011/04/24)
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- Molecular modeling study and synthesis of quinazolinone-arylpiperazine derivatives as α1-adrenoreceptor antagonists
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Three series of new 2-[(4-substituted piperazin-1-yl) methyl]quinazolin- 4(3H)-ones 4a-c, Ethyl 6,7-dimethoxy-4-oxo-3-[2-(4-substituted piperazin-1-yl)acetamido/propanamido]-3,4-dihydroquinazoline-2-carboxylates 9a-f and their 2-methyl analogues 13a-l were designed and synthesized as promising α1-adrenoceptor antagonists. The final compounds were evaluated for their in vivo hypotensive activity in normotensive cats. The most potent hypotensive quinazolinone derivatives 4b, 9e, 13i, 13j were further tested on isolated thoracic aortic rings of male Wister rats. All the tested compounds displayed α1-blocking activity with IC50 ranging from 0.2 to 0.4 mM less than prazosin. Furthermore, in the present work, molecular modeling study using Accelrys Discovery Studio 2.1 software was performed by mapping the synthesized compounds to the α1- adrenoceptor antagonist hypothesis in order to predict their mechanism of action. Compound 13j which has the best-fitting score displayed the highest in vivo and in vitro activity among the tested compounds.
- Abou-Seri, Sahar Mahmoud,Abouzid, Khaled,Abou El Ella, Dalal A.
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scheme or table
p. 647 - 658
(2011/03/22)
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- Synthesis, spectral, powder X-ray diffraction and antimicrobial studies of some transition metal(II) complexes of Schiff base derived from 3-[(2-hydroxy-6-methylquinolin-3-ylmethylene)-amino]-2-methyl-3H-quinazoline-4- one
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Complexes of the type ML2 and M'L [where, M = Cu(II), Co(II), Ni(II) and Mn(II); M' = Zn(II), Cd(II) and Hg(II)] with the Schiff base L = 3-[(2-hydroxy-6-methylquinolin-3-ylmethylene)-amino]-2-methyl-3H-quinazoline-4- one, (HMQMAMQ) have been synthesized. Their characterizations have been done by elemental analysis, conductance data, magnetic susceptibility measurements, 1H NMR, electronic, IR, ESR and X-ray studies. Ligand field parameters of some of the complexes have also been calculated. On the basis of spectral studies, complexes of Co(II), Ni(II) and Mn(II) have been assigned octahedral geometry, where as the complexes of Zn(II), Cd(II) and Hg(II) have been assigned tetrahedral geometry. The complex of Cu(II) has been assigned distorted octahedral geometry. The ligand and its complexes have also been screened for their antimicrobial activity against selected fungi and bacteria.
- Siddappa,Reddy, Patil Chandrakant,Kote, Mallikarjun,Reddy, Tukaram,Tambe, Mahesh,Metre, Mallikarjun
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experimental part
p. 4511 - 4516
(2012/03/09)
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- Conversion of solar energy to chemical energy
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The rate of evolution of hydrogen from water by photochemical process using solar energy has been investigated employing fourteen metal complexes as catalysts, ten electron relays, three electron donors and two co-catalysts in different permutation and combinations. The effect of varying reaction conditions like temperature, concentration and pH have also been investigated for the optimum production of hydrogen by the photochemical cleavage of water molecules.
- Ranganayakulu,Murthy
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p. 309 - 316
(2011/08/09)
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- Identification of novel quinazolin-4(3H)-ones as inhibitors of thermolysin, the prototype of the M4 family of proteinases
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A combinatorial series of novel quinazolin-4(3H)-ones were synthesised and their structures were established based on spectroscopic data (IR, NMR, EI-MS, and FAB-MS). The compounds were tested for inhibition of the zinc metalloproteinase thermolysin (TLN) utilizing a chemical array-based approach. Some of the compounds were found to inhibit TLN, with IC50 values ranging from 0.0115 μM (compound 3) to 122,637 μM (compound 29). Compound 3 [3-phenyl-2-(trifluoromethyl) quinazolin-4(3H)-one] (IC50 = 0.0115 μM) and compound 35 [3-(isopropylideneamino)-2,2-dimethyl-2,3-dihydroquinazolin-4 (1H)-one] (IC50 = 0.2477 μM) were found to be the most potent inhibitors.
- Khan, Mahmud Tareq Hassan,Khan, Rasool,Wuxiuer, Yimingjiang,Arfan, Mohammad,Ahmed, Manzoor,Sylte, Ingebrigt
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experimental part
p. 4317 - 4327
(2010/09/12)
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- Syntheses and antimicrobial activities of derivatives of 3-amino-2-methyl-quinazolin-4-(3H)-one
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In the present study, 3-amino-2-methyl-quinazolin-4-(3H)-one (1) have been synthesized by the reaction of N-acetyl anthranilic acid with acetic anhydride followed by treating the mixture with hydrazine hydrate in pyridine. Compound 1 on treating with chloro acetyl chloride gives 3-chloroethanoylamino-2-methyl-quinazolin-4-(3H)-one (2). The final compounds 4a-g were obtained by reacting the substituted derivative 2 with aliphatic and aromatic secondary amines. The structural assignment of this compound 4a-g has been made on the basis of elemental analysis, IR and 1H NMR data. The synthesized compounds were screened for in vitro growth inhibiting activity by determining the minimum inhibitory concentration against different strains of bacteria and fungi. Compounds 4a, 4b, 4e and 4g exhibit highest antibacterial activity and compounds 4a, 4b, 4d and 4e showed better antifungal activity.
- Chhabra,Tiwari, Ravi
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experimental part
p. 3390 - 3396
(2010/11/17)
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- Synthesis of poly(pyridazinoquinazolones)
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A model reaction of 2-alkyl-3-aminoquinazolones with α-dicarbonyl compounds benzil and its 4,4′-derivatives, acenaphthenequinone and isatin was studied for the first time. The reaction proceeded in pentafluorophenol and led to the formation of new heterocyclic systems. This approach was used in the synthesis of new thermostable polyheteroarylenes with fluorescent properties, viz., poly(pyridazinoquinazolones).
- Ponomarev,Razorenov,Petrovskii
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p. 2376 - 2384
(2014/05/06)
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- Synthesis and antiviral bioactivities of 2-aryl- or 2-methyl-3- (substituted- benzalamino)-4(3H)-quinazolinone derivatives
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A simple and general method has been developed for the synthesis of various 4(3H)-quinazolinone derivatives by the treatment of the appropriate 3-amino-2-aryl-4(3H)-quinazolinone with a substituted benzaldehyde in ethanol. The structures of the compounds were characterized by elemental analysis, IR, 1H-NMR and 13C-NMR spectra. The title 2-aryl- or 2-methyl-3-(substituted-benzalamino)-4(3H)-quinazolinone compounds III-1-III-31 were found to possess moderate to good antiviral activity. Semi-quantitative PCR and Real Time PCR assays were used to ascertain the target of action of compound III-31 against TMV. The studies suggest that III-31 possesses antiviral activity due to induction of up-regulation of PR-1a and PR-5, thereby inhibiting virus proliferation and movement by enhancement of the activity of some defensive enzyme.
- Gao, Xingwen,Cai, Xuejian,Yan, Kai,Song, Baoan,Gao, Lili,Chen, Zhuo
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p. 2621 - 2642
(2008/03/18)
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- Quinazolin-4-one derivatives
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A medicament having an inhibitory activity against hematopoietic prostaglandin D2 synthase, which comprises as an active ingredient a compound represented by the following general formula (I) or a salt thereof: wherein X represents a group represented by the formula —N═C(R5)— or the formula —NH—CH(R5)—, R1, R2, R3, and R4 represent a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, or a hydroxy group, R5 represents a C1 to C6 alkyl group or a C6 to C10 aryl group, and R represents an amino group.
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Page/Page column 18
(2010/11/24)
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- Synthesis and pharmacological investigation of some novel 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones as histamine H 1-receptor blockers
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A series of 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones were synthesized from 3-amino-2-methyl-(3H)-quinazolin-4-one. Their structures were confirmed by spectral data (IR, NMR and MS) and the purity was ascertained by microanalysis. When tested for H1-receptor blocking activity on isolated guinea pig ileum all the test compounds inhibited histamine induced contraction whereas compound 5 (IC50 0.22 · 103 ng/ml) was found to be four times more potent than chlorpheniramine maleate (IC50 1 · 103 ng/ml) and it showed lesser sedation (8%) than the standard (32%).
- Alagarsamy
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p. 753 - 755
(2007/10/03)
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- Studies on quinazolines: Part II-Synthesis and antimicrobial evaluation of some 2,2-disubstituted-3,3-biquinazolin-4(3H)-ones
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N-(2-Styryl-, 2-p-chlorostyryl- or 2-p-nitrostyryl-4-oxo-3H-quinazolin-3-yl)-2-aminobenzamides 6a-c react with triethyl orthoesters to furnish some new 2-styryl-, 2-p-chlorostyryl- or 2-p-nitrostyryl-2-substituted-3,3-biqui-nazolin-4(3H)-ones (7a-c-9a-c). An alternative synthesis of (7-9)b has been accomplished by reaction of acetylanthranil with 2-amino-2-styryl-, 2-p-chlorostyryl- or 2-p-nitrostyryl-quinazolin-4(3H)-ones 4a-c. The synthesised products are tested for antimicrobial activities using methaqualone as reference standard.
- Wasfy
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p. 3102 - 3107
(2007/10/03)
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- Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-methyl-3-substituted quinazolin-4-(3H)-ones
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A series of novel 2-methyl-3-substituted quinazolin-4-(3H)-ones have been synthesized by treating (2-methyl-4-oxo-3H-quinazolin-3-yl)dithiocarbamic acid methyl ester with different amines, the starting material dithiocarbamate was synthesized from anthranilic acid. The compounds synthesized were investigated for analgesic, anti-inflammatory and antibacterial activities. All the test compounds exhibited significant activity, the compounds VA2, VA3 and VA4 shown more potent analgesic activity, and the compounds VA3 and VA4 shown more potent anti-inflammatory activity than the reference compound diclofinac sodium.
- Alagarsamy, Veerachamy,Murugananthan, Gopal,Venkateshperumal, Ramachandran
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p. 1711 - 1714
(2007/10/03)
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- Kinetics of hydrolysis of 2-methyl/ phenyl-3-(2′-hydroxybenzalamino)quinazolin-4(3H)-one
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Kinetics of hydrolysis of 2-methyl-3-(2′-hydroxybenzalamino)quinazolin-4(3H)-one (MHBQ) and 2-phenyl-3-(2′-hydroxybenzalamino)quinazolin-4(3H)-one (PHBQ) have been studied. Rate coefficients have been measured for the alkaline hydrolysis of MHBQ and PHBQ in 70% (v/v) dioxane-water at various temperatures. The enthalpies and entropies of activation have been evaluated. The hydrolysis of MHBQ and PHBQ follows first order kinetics in both the substrate and the base. The relative rates of hydrolysis and activation parameters have been used to suggest the mechanism of the reactions.
- Laxma Reddy,Upender,Adinarayana Reddy
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p. 712 - 715
(2007/10/03)
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- Lithiation of 3-(acylamino)-2-unsubstituted-, 3-(acylamino)-2-ethyl-, and 3-(acylamino)-2-propyl-4(3H)-quinazolinones: Convenient syntheses of more complex quinazolinones
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3-(Pivaloylamino)- and 3-(acetylamino)-4(3H)-quinazolinones react with alkyllithium reagents to give 1,2-addition products in very good yields. Lithiation takes place with LDA and is regioselective at position 2. The lithium reagents thus obtained react with a variety of electrophiles to give the corresponding substituted derivatives in very good yields. Reactions of the lithium reagents with iodine give oxidatively dimerized cyclic structures. 3-(Pivaloylamino)- and 3-(acetylamino)-2-ethyl-4(3H)-quinazolinones and 3-(pivaloylamino)- and 3-(acetylamino)-2-propyl-4(3H)-quinazolinones are lithiated at the benzylic position with LDA. The lithium reagents so produced also react with a variety of electrophiles to give the corresponding 2-substituted-4(3H)-quinazolinone derivatives in very good yields. However, lithiation of 3-(acylamino)-2-(1-methylethyl)-4(3H)-quinazolinones was unsuccessful, as were lithiations of compounds having a diacetylamino group at position 3. The amide groups have been cleaved in good yield under basic or acidic conditions from some of the products to provide access to the free amino compounds.
- Smith,El-Hiti,Abdel-Megeed,Abdo
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p. 647 - 655
(2007/10/03)
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- Quinazolinone derivatives: Synthesis and binding evaluation on cholecystokinin receptors
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A series of 2-methyl-3-amino-4(H)-quinazolinone and of 2-phenyl-3-amino-4(H)-quinazolinone derivatives were synthesized and examined for their CCK receptor affinities. These compounds displayed micromolar affinities for CCK-B rather than CCK-A receptor and the obtained results confirm that the 4(3H)-quinazolinone nucleous represent a useful template for the development of selective CCK-B receptor ligands.
- Varnavas,Lassiani,Luxich,Zacchigna,Boccu
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p. 333 - 339
(2007/10/03)
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- Regiospecific electrophilic substitution of aminoquinazolines: directed lithiation of 3-(pivaloylamino)- and 3-(acetylamino)-2-methylquinazolin-4(3H)-ones
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The 2-methyl group in 3-(pivaloylamino)- and in 3-(acetylamino)-2-methylquinazolin-4(3H)-ones has been lithiated with butyllithium.The lithium reagents thus obtained react with a variety electrophiles (benzophenone, methyl iodide, D2O, cyclohexanone, acetophenone, phenyl isocyanate) to give the corresponding substituted derivatives in very good yields.The amino group has been cleaved in good yield under basic conditions for one model case to provide convenient access to 3-amino-2-ethylquinazolin-4(3H)-one.The NMR spectra of the 2-substituted 3-acylaminoquinazolin-4(3H)-ones show diastereotopism of the CH2 group at position 2.
- Smith, Keith,El-Hiti, Gamal A,,Abdo, Mohamed A.,Abdel-Megeed, Mohamed F.
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p. 1029 - 1034
(2007/10/02)
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- Synthesis and reactions of 3-amino-2-methyl-4(3H)-quinazolinone derivatives
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3-Amino-2-methyl-4(3H)-quinazoline (2) has been synthesized by treating 2-methylbenzoxazinone (1) with hydrazine hydrate.Reaction of quinazolinone (2) with phenyl isothiocyanate and phenyl isocyanate furnish the corresponding aminocarbothiamide and aminocarbamide derivatives (3 and 5), respectively, which on reaction with malonic acid in acetyl chloride afford thiobarbituric and barbituric acid derivatives (4 and 6), respectively.Behaviour of compound 5 towards different aldehydes, ketones and imides have been investigated.
- Yassin, F. A.,Eissa, A. M. F.,Wasfy, A. A. F.
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p. 1193 - 1196
(2007/10/02)
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- Substituted polycylic derivatives of the 9-oxo-1,9a,10-triaza-9-hydroanthracene and method for coloring of native or synthetic materials
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Derivatives of 9-oxo-1,9a,10-triaza-9-hydroanthracene of the general formula I STR1 with the exception of three compounds in which R denotes a hydrogen atom, halogen atom, an alkyl-C1 -C4, alkoxy-C1 -C4 or denotes a trihalogenomethyl group, a --CO--NH2, --CO--NH--(alkyl-C1 -C4) or --CO--N(alkyl-C1 -C4)2 group or phenyl, alkyl-C1 -C4, --NH2, --NH(alkyl-C1 -C4), --N(alkyl-C1 -C4)2 or an alkylene-C1 -C4 --OSO3 H group, bound via the bridge member --S--, --SO--or --SO2 --, a or a fused-on 4- to 7-membered isocycle or heterocycle, which itself can be part of a polycyclic system, from the series consisting of naphthalene, acenaphthene, phenanthrene and indole, x denotes an integer from 1 to 4, where for x>1 R can be identical or different, and z denotes a fused-on 4- to 7-membered isocycle or heterocycle, which itself can be part of a polycyclic system, from the series consisting of naphthalene, acenaphthene, phenanthrene and indole, in which each of the 4- to 7-membered isocycles or heterocycles and each of the polycyclic systems mentioned can be substituted, processes for their preparation and their use for the coloring of natural or synthetic materials.
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- Reaction of 2-Aminobenzoylhydrazines with Carboxylic Acids: Formation of Quinazolin-4(3H)-one, 1,3,4-Oxadiazole and 1,3,4-Benzotriazepin-5-one Derivatives
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Reactions of 2-aminobenzoylhydrazines with aliphatic acids give 1-(2'-acylaminobenzoyl)-2-acylhydrazines (4) which are cyclised to 3-amino-2-alkylquinazolin-4(3H)-ones (6).Aromatic acids react with 2-aminobenzoylhydrazines to give a mixture of 1-(2'-amino
- Reddy, P. S. N.,Reddy, P. Pratap
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p. 763 - 765
(2007/10/02)
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- Aziridination of Olefinic and Hydroxyolefinic Fatty Esters
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Reactions of olefinic (Ia-c) and hydroxyolefinic (Id,e) fatty acid esters with nitrene (Y-N:), generated in situ by lead tetraacetate oxidation of 3-amino-2-methyl-4-oxoquinazoline, result in the formation of the corresponding N-substituted aziridine derivatives (IIa-e).
- Ahmad, M. B.,Rauf, Abdul,Osman, S. M.
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p. 1140 - 1141
(2007/10/02)
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- Synthesis of Quinazolinylpyrimidinediones and Their Anti-inflammatory Activity
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Hexahydro-1--3-aryl-2-thioxopyrimidine-4,6-diones (IV) have been prepared and converted into hexahydro-1--3-aryl-5-benzyliden-2-thioxopyrimidine-4,6-diones (V) and hexahydro-1-2-alkyl-4(
- Kumar, Atul,Singh, S.,Saxena, A. K.,Shanker, K.
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p. 443 - 447
(2007/10/02)
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- Synthesis of 3-Amino-4-(3H)-quinazolinones from N-(2-Carbomethoxyphenyl) Imidate Esters
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Novel difunctional aromatic synthons consisting of N-(2-carbomethoxyphenyl) imidate esters were synthesized by treatment of methyl anthranilate esters with aliphatic ortho esters.Treatment of the imidates with hydrazine, methylhydrazine, and phenylhydrazine yielded only quinazolinones and not isomeric 1,3,4-benzotriazepin-5-ones.The type of products obtained gave information relevant to elucidation of the mechanism of cyclization and the relative reactivities of the ester and imidate groups.
- Leiby, Robert W.
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p. 2926 - 2929
(2007/10/02)
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- A New Synthesis of 2-Aryl-3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones
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The reaction of 2-aryl-3,1-benzoxazine-4-ones (1) and hydrazine hydrate in refluxing xylene yields 2-aryl-3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones in 55-74percent yield.In basic conditions this reaction, however, gives 2-aryl-3-aminoquinazolin-4(3H)-one
- Reddy, Ch. K.,Reddy, P. S. N.,Ratnam, C. V.
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p. 902 - 904
(2007/10/02)
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- Synthesis and antimicrobial activity of noval quinazolone derivatives
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Three novel series of 4-oxoquinazoline derivatives were prepared and evaluated as potential antimicrobial agents. Evaluation of the antimicrobial activity of a variety of 4-substituted-1-thiosemicarbazides, 3,4-disubstituted thiazolines, and 3-substituted-5-thiazolidones reveals that the majority possess significant in vitro activity against Gram-positive organisms. Some derivatives also exhibited antifungal activity.
- Habib,Khalil
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p. 982 - 985
(2007/10/02)
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- Factors Which Influence the Formation of Oxadiazoles from Anthranilhydrazides and Other Benzoylhydrazines
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The cyclization of o-aminobenzoylhydrazine (1a) and its 5-methyl derivative 1b with four equivalents and with one equivalent of triethyl orthoacetate (TEOA) was studied. 3-Amino-2-methyl-4(3H)-quinazolinone (2a), 3,4-dihydro-2-methyl-5H-1,3,4-benzotriazepin-5-one (3a) and an imino ether derivative of 2a, N-ethanimidic acid ethyl ester (4a) were obtained from the reaction of 1a with four equivalents of TEOA.These results were compared with those of Merour who isolated 2a and 3a using the same conditions.When 1a was treated with one equivalent of TEOA, 2a, 3a, and a new product, 2-(5-methyl-1,3,4-oxadiazol-2-yl)benzenamine (5a) were produced, and 4a was not.Similar results were obtained with the reactions of 1b with TEOA.Authentic samples of oxadiazoles 5a and b were prepared by alternate routes.Novel acid-catalyzed rearrangements of benzotriazepinones 3a and b, to mixtures of aminoquinazolinones 2a and b and oxadiazoles 5a and b, respectively, were found.The different relative amounts of aminoquinazolinones 2 and oxadiazoles 5 which were produced from these rearrangements allowed us to choose between two potential mechanism for these interesting rearrangements.Treatment of 5-nitrobenzoylhydrazine (37) with four equivalents of TEOA gave three products which were characterized, but did not lead to benzotriazepinone formation.
- Peet, Norton P.,Sunder, Shyam
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p. 1807 - 1816
(2007/10/02)
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- Synthesis of Pyrazole, Quinoline and Quinazoline Derivatives: Part II - Reactions of o-Aminobenzoic Acid Hydrazide with Acetylacetone and Benzoylacetone
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o-Aminobenzoic acid hydrazide (I) reacts with acetylacetone (II) and benzoylacetone (V) to give pyrazole, quinoline and quinazoline derivatives.The mechanism involved in their formation has been rationalised.
- Phadtare, S. K.,Kamat, S. K.,Panse, G. T.
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p. 499 - 501
(2007/10/02)
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- Synthesis of Pyrazolone and Quinazolone Derivatives from Aromatic Acid Hydrazide and Ethyl Acetoacetate
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The reaction between unsymmetrical acid hydrazide and ethyl acetoacetate gives pyrazolone (II) and quinazolone (III) derivatives.The formation of II and III has been rationalised.
- Phadtare, S. K.,Kamat, S. K.,Panse, G. T.
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p. 212 - 213
(2007/10/02)
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