- Synthesis of novel bioactive phthalimido-4-methyl pentanoateorganotin(IV) esters with spectroscopic investigation
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The synthesis of monomer, dimer, tricyclohexyl- and triphenyl-tin(IV) complexes with phthalimido-4-methyl pentanoic acid (PMPA) are described and characterized by FT IR, CHN analyzer, 1H, 13C 119Sn NMR and 119mSn M?ssbauer spectroscopic techniques. In vitro ED50, anti-tumor (phytotoxic), anti-yeast, blood pressure and heart rate effect, and bactericidal, fungicidal as well as analgesic bioassays of complexes are also be carried out. The ligand (PMPA) shows excellent analgesic activity while the dimer exhibit strong biocidal and excellent anti-tumor behavior besides of tri-organotin(IV) complexes.
- Ashfaq, Muhammad
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- Amino acid conjugates of aminothiazole and aminopyridine as potential anticancer agents: Synthesis, molecular docking and in vitro evaluation
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Purpose: The development of resistance to available anticancer drugs is increasingly becoming a major challenge and new chemical entities could be unveiled to compensate this therapeutic failure. The current study demonstrated the synthesis of 2-aminothiazole [S3 (a-d) and S5(a-d)] and 2-aminopyridine [S4(a-d) and S6(a-d)] derivatives that can target multiple cellular networks implicated in cancer development. Methods: Biological assays were performed to investigate the antioxidant and anticancer potential of synthesized compounds. Redox imbalance and oxidative stress are hallmarks of cancer, therefore, synthesized compounds were preliminarily screened for their antioxidant activity using DPPH assay, and further five derivatives S3b, S3c, S4c, S5b, and S6c, with significant antioxidant potential, were selected for investigation of in vitro anticancer potential. The cytotoxic activities were evaluated against the parent (A2780) and cisplatin-resistant (A2780CISR) ovarian cancer cell lines. Further, Molecular docking studies of active compounds were performed to determine binding affinities. Results: Results revealed that S3c, S5b, and S6c displayed promising inhibition in cisplatin-resistant cell lines in comparison to parent cells in terms of both resistance factor (RF) and IC50 values. Moreover, S3c proved to be most active compound in both parent and resistant cell lines with IC50 values 15.57 μM and 11.52 μM respectively. Our docking studies demonstrated that compounds S3c, S5b, and S6c exhibited significant binding affinity with multiple protein targets of the signaling cascade. Conclusion: Anticancer activities of compounds S3c, S5b, and S6c in cisplatin-resistant cell lines suggested that these ligands may contribute as lead compounds for the development of new anticancer drugs.
- Ali, Tahir,Imran, Muhammad,Li, Jing Bo,Li, Shupeng,Nadeem, Humaira,Naz, Shagufta,Sarwar, Sadia,Shah, Fawad Ali,Tan, Zhen
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p. 1459 - 1476
(2021/04/19)
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- Synthesis of new amides based on N-Phthaloyl-α-Amino Acids
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N-phthaloyl derivatives of aliphatic α-amino acids were synthesized using phthalanhydride under standard conditions. The optimization reaction carried out by the thermal method to obtain the amides of these N-phthaloyl amino acids resulted in transimitted rather than amidation. The target amides of N-phthaloyl-α-amino acids were obtained by acylation of the amine with the corresponding acid chloroanhydrides in dichloromethane. These results were compared with the results of a similar acylation in a non-polar solvent (benzene). The dependence of the direction of the reaction on the duration of the acylation and the amount of amine used was established. The conditions for the formation of the corresponding N-phthaloyl-α-amino acid amides and asymmetric phthalic acid diamides were found. It is noteworthy that the formation of diamides is directly proportional to the equivalent amount of amine and the duration of the reaction, which makes it possible to purposefully control the synthesis in one reactor.
- Tukhtaev,Yusupov,Vinogradova
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p. 3049 - 3058
(2021/05/28)
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- Synthesis and study of modified polyvinyl alcohol containing amino acid moieties as anticancer agent
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A series of new phthalimides compounds[3-7]a-i were synthesized from reaction of Malic anhydride, phthalic anhydride, nitro phthalic anhydride, 2-phenyl-4H-benzo[d][1,3]oxazin-4-one, 2-(4-nitrophenyl)-4H-benzo[d][1,3]oxazin-4-one with different amino acids as glycine, alanine, valine, leucine, isoleucine, serine, threonine, tyrosine and Phenyl alanine [1]a-i under fusion conditions. Compounds [3-7]a-i react with SOCl2 in the presence of benzene to produce compounds [8-12]a-i. Chemical modification of Poly(vinyl alcohol)were obtained by reaction of PVA with compounds [8-12]a-i using the dimethyl formamide to give compounds [13-17]a-i. The structure of the synthesized compounds was characterized by their analytical and spectral data as, IR spectra, 1H, 13C-NMR, Elemental analysis (CHN), UV-Vis Spectroscopy, Scanning electron microscopy (SEM), Antibacterial activity were screened via two kinds of bacteria. Also, anticancer activity were examined for most of the modified polyvinyl alcohol.
- Samir, Ali H.,Saeed, Ruwaidah S.,Matty, Fadhel S.
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p. 286 - 294
(2018/03/21)
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- Bioinspired Deamination of α-Amino Acid Derivatives Catalyzed by a Palladium/Nickel Complex
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An efficient bioinspired deamination method of both natural and unnatural amino acid derivatives has been developed. This method provides easy access to a wide variety of useful α, β-unsaturated carbonyl compounds. The reaction is realized with two transition metal catalysts (palladium and Nickel) in-easy handling procedure. A possible reaction pathway is also proposed and the control experiments support the involvement of the palladium-catalyzed inert sp3 C?H activation as one of the key steps. (Figure presented.).
- Deng, Gongtao,Chen, Jie,Sun, Wangbin,Bian, Kehan,Jiang, Yaojia,Loh, Teck-Peng
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supporting information
p. 3900 - 3905
(2018/09/12)
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- Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)-H Direct Fluorination
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A coordinating, copper-catalyzed direct α-C(sp3)-H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable, single absolute configurations of the target compounds.
- Wei, Qiang,Ma, Yao,Li, Li,Liu, Qingfei,Liu, Zijie,Liu, Gang
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supporting information
p. 7100 - 7103
(2018/11/24)
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- 1-Imidoalkylphosphonium salts with modulated Cα–P+ bond strength: synthesis and application as new active α-imidoalkylating agents
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An effective synthesis of the hitherto unknown 1-imidoalkylphosphonium salts has been developed in the reported study. The crucial step in the method included the decarboxylative α-methoxylation of N-phthaloyl- or N-succinylamino acids to the corresponding N-(1-methoxyalkyl)imides, followed by the displacement of the methoxy group by the triarylphosphonium group through melting of the imide derivative with triarylphosphonium tetrafluoroborate. The imidoalkylating properties of the obtained 1-imidoalkylphosphonium salts were tested using the Tscherniac–Einhorn-type reaction with aromatic hydrocarbons as a model reaction. It was found that the Cα–P+ bond strength can be considerably reduced and the imidoalkylation of arenes can be markedly facilitated using 1-imidoalkylphosphonium salts derived from triarylphosphines with electron-withdrawing substituents such as tris(m-chorophenyl)phosphine, tris(p-chlorophenyl)phosphine and tris[p-(trifluoromethyl)phenyl]phosphine. Microwave irradiation also considerably facilitates the cleavage of the highly polar Cα–P+ bond.
- Adamek, Jakub,Mazurkiewicz, Roman,W?grzyk, Anna,Erfurt, Karol
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supporting information
p. 1446 - 1455
(2017/08/02)
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- Phthiobuzonum derivative and its preparation and use
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The invention relates to a ftibamzone derivative and a preparation method and an application thereof, and belongs to the technical field of ftibamzone medicament synthesis. Pharmacological experiments prove that the ftibamzone derivative of the invention has obvious cytotoxic activity and antiviral activity, and can be used for treating viral diseases such as tumor, herpes, trachoma, and the like.
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Paragraph 0134; 0136
(2016/11/09)
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- BORONIC ACID CATALYSTS AND METHODS OF USE THEREOF FOR ACTIVATION AND TRANSFORMATION OF CARBOXYLIC ACIDS
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The present application provides methods and catalysts for activation of carboxylic acids for organic reactions. In particular, methods are disclosed for direct nucleophilic addition reactions, such as, amidation reactions with amines, cycloadditions, and conjugate additions, using boronic acid catalysts of formula I, II or III: Also included are novel boronic acid catalysts of formula IV, V and III:
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Page/Page column 45-46
(2012/09/10)
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- Synthesis and antiviral activity of novel 1,3,4-thiadiazine derivatives
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A series of novel 1,3,4-thiadiazine derivatives were synthesized via chemical optimization on phthiobuzone. Their anti-herpes simplex virus (HSV) activities in vitro were also tested. Several compounds exhibited more highly potent anti-HSV activity and much higher selectivity index (SI) values than those of phthiobuzone. The most potent anti-HSV compound was 4f, which showed marked inhibition against HSV-1 (IC50=77.04μg/ml) and HSV-2 (IC50=30.00μg/ml). Meanwhile it had low cytotoxicity (CC 50=1000.00μg/ml), resulting in high (SIHSV-1= 12.98, SIHSV-2=33.33, respectively). Furthermore, a computational study for prediction of absorption, distribution, metabolism, excretion (ADME) properties of compound 4f was performed by determination of topological polar surface area, absorption and Lipinski parameters.
- Yang, Yajun,Feng, Ziming,Jiang, Jianshuang,Yang, Yanan,Pan, Xiandao,Zhang, Peicheng
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scheme or table
p. 1016 - 1019
(2011/10/08)
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- The synthesis of N-acyl-2-hydroxymethyl aziridines of biological interest
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A practical synthesis of the title compounds from protected amino acylazides is described. All the compounds might be considered as a novel class of dipeptide isostere precursors; they all induce lymphocyte proliferation and protein production as observed from preliminary biological tests.
- Medjahed,Tabet Zatla,Kajima Mulengi,Baba Ahmed,Merzouk
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p. 1211 - 1213
(2007/10/03)
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- Imides
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Cyclic imides are inhibitors of tumor necrosis factor α and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-(2,6-dioxo-3-piperidinyl)-4-azaisoindoline-1,3-dione.
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- Cyclic amides
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Cyclic amides are inhibitors of tumor necrosis factor and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 3-phenyl-3-(1-oxoisoindolin-2-yl)propionamide.
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- Ring closure of N-phthaloylglutamines
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Cyclic imides are inhibitors of tumor necrosis factor α and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-(2,6-dioxo-3-piperidinyl)-4-azaisoindoline-1,3-dione.
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- DESIGN AND SYNTHETIC APPLICATIONS OF NEW HETEROMETALLACYCLES
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The reaction of cyclic anhydrides with Ni(0) complexes lead to the formation of nickelacycles by oxidative addition followed by decarbonylation.The preparation of chiral nickelacycles from anhydrides derived from amino acids and their reactivity is described.The formation of new heteropalladacycles by C-H activation or transmetallation reactions and their reactivity will be also discussed.
- Echavarren, Antonio M.,Cardenas, Diego J.,Castano, Ana M.,Cuerva, Juan M.,Mateo, Cristina
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p. 549 - 558
(2007/10/02)
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- SULFUR YLIDES. 3. SYNTHESIS OF KETO-GROUP STABILIZED AMINO-CONTAINING SULFUR YLIDES FROM AMINO ACIDS
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An effective path of synthesis was developed of new synthetic intermediates, the optically active, keto-group stabilized amino-substituted sulfur ylides.
- Tolstikov, G. A.,Galin, F. Z.,Lakeev, S. N.,Khalilov, L. M.,Sultanova, V. S.
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p. 535 - 541
(2007/10/02)
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