- Hantzsch 1,4-dihydropyridine synthesis in aqueous ethanol by visible light
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A highly efficient environment-friendly Hantzsch 1,4-dihydropyridine synthesis under visible light in aqueous ethanol has been achieved in excellent yield via a one-pot three component reaction of various types of aliphatic and aromatic aldehydes with ethyl acetoacetate and ammonium hydroxide solution.
- Ghosh, Somnath,Saikh, Forid,Das, Jhantu,Pramanik, Arun Kumar
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- Aqua-mediated one-pot synthesis of Biginelli dihydropyrimidinone/thiones (DHPMs), Hantzsch dihydropyridines (DHPs), and polysubstituted pyridines sonocatalyzed by metal-supported nanocatalysts
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In this work, catalyst composition-activity relationship of supported catalysts in Biginelli and Hantzsch reactions was investigated under mild conditions. Biginelli dihydropyrimidinone/thiones were prepared over Fe-Cu/ZSM-5 as an efficient, convenient, and environmentally benign catalyst under ultrasonic irradiation in aqueous media in very good yields. The Fe-Cu/ZSM-5-catalyzed synthesis of 1,4-dihydropyridines and their aromatization to polysubstituted pyridines and also a new one-pot, two-step, and sequential protocol for the synthesis of pyridine derivatives, employing an aldehyde, ethyl acetoacetate, and ammonium acetate under the same green experimental conditions were illustrated. Three-component condensation in the presence of supported reagent with operational simplicity, inexpensive reagents, short reaction time, high yield of products, and use of non-toxic reagents makes this synthetic protocol an attractive one.
- Safa, Kazem D.,Esmaili, Maryam,Allahvirdinesbat, Maryam
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- 2-Hydroxyethylammonium acetate: An efficient and reusable homogeneous catalyst for the synthesis of Hantzsch 1, 4-dihydropyridines
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2-Hydroxyethylammonium acetate ionic liquid was found to be an excellent catalyst for the one-pot synthesis of 1,4-dihydropyridine derivatives via Hantzsch reaction of ethyl acetoacetate or acetoacetanilide, ammonium acetate, and various aromatic aldehyde
- Kang, Li-Qin,Cao, Zhi-Jun,Lei, Ze-Jun
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- Revisiting ageless antiques; synthesis, biological evaluation, docking simulation and mechanistic insights of 1,4-Dihydropyridines as anticancer agents
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The historic DHP nucleus was serendipitously discovered by Arthur Hantzsch about 130 years ago and is still considered a hidden treasure for various pharmacological activities. Twenty-one DHP analogues were synthesized using the expedient one pot Hantzsch synthesis for screening as anticancer agents. Initially, the in vitro anti-proliferative single dose against a panel of 18 cancer cell lines showed that compounds 11b and 8f were the superlative candidates regarding their antitumor effect (GI% mean = 66.40% and 50.42%, correspondingly) compared to cisplatin (GI% mean = 65.58%) and doxorubicin (GI% mean = 74.56%). Remarkably, compound 11b showed a remarkable MDA-MB-468 anticancer activity (GI%=80.81%), higher than cisplatin (64.44%) and doxorubicin (76.72%), as well as strong antitumor activity against lung cancer A549 (GI%= 83.02%), more powerful than both cisplatin and doxorubicin. Compound 11b exhibited an exceptional anticancer activity against lung cancer cell line (A549) as its GI50 in nanomolar was (540 nM) with a 9-fold increase greater than cisplatin (GI50 = 4.93 μM) and with a selectivity index = 131 to cancer cells over normal cells. Further mechanistic investigations proved that DHPs anticipate simultaneously TOPI and RTKs (VEGFR-2, HER-2 and BTK) which can stimulate BAX/BAK and the executioner caspases via rtPCR studies.
- Sidhom, Peter A.,El-Bastawissy, Eman,Salama, Abeer A.,El-Moselhy, Tarek F.
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- Silica sulfuric acid: An efficient heterogeneous catalyst for the one-pot synthesis of 1,4-dihydropyridines under mild and solvent-free conditions
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A series of 1,4-dihydropyridines have been prepared by a one-pot condensation of aldehydes, ethyl acetoacetate, and ammonium acetate in the presence of a heterogeneous catalyst silica sulfuric acid at room temperature under solvent-free condition. This new protocol has the advantage of short reaction time and excellent yields, and is an environmentally benign route to the synthesis of 1,4-dihydropyridines.
- Datta, Bandita,Pasha, M. Afzal
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- Design, synthesis and evaluation of dialkyl 4-(benzo[d][1,3]dioxol-6-yl)-1, 4-dihydro-2,6-dimethyl-1-substituted pyridine-3,5-dicarboxylates as potential anticonvulsants and their molecular properties prediction
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The present study is on the development of dialkyl 4-(benzo[d][1,3]dioxol- 6-yl)-1,4-dihydro-2,6-dimethyl-1-substituted pyridine-3,5-dicarboxylate derivatives as isosteric analogues of isradipine and nifedipine, by the replacement of benzofurazanyl and 2-
- Prasanthi,Prasad,Bharathi
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p. 516 - 525
(2013/10/01)
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- Synthesis of some new 1,4-dihydropyridine derivatives through a facile one-pot Hantzsch condensation catalyzed by triethylamine
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A facile and efficient synthesis of new 1,4-dihydropyridine derivatives was reported via Hantzsch three-component condensation reaction of aldehydes or formylphenylboronic acids, ethyl acetoacetate, and ammonium acetate in the presence of a catalytic amount of triethylamine under solvent-free conditions. The method described here offers several advantages including high yields, short reaction times, and simple work-up procedure.
- Ghalem, Wassima,Boulcina, Raouf,Debache, Abdelmadjid
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experimental part
p. 733 - 737
(2012/05/20)
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- Silica Sulfuric Acid: An Efficient Heterogeneous Catalyst for the One-Pot Synthesis of 1,4-Dihydropyridines under Mild and Solvent-Free Conditions
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A series of 1,4-dihydropyridines have been prepared by a one-pot condensation of aldehydes, ethyl acetoacetate, and ammonium acetate in the presence of a heterogeneous catalyst silica sulfuric acid at room temperature under solvent-free condition. This new protocol has the advantage of short reaction time and excellent yields, and is an environmentally benign route to the synthesis of 1,4-dihydropyridines.
- Datta, Bandita,Pasha, M. Afzal
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p. 1180 - 1184
(2016/04/10)
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- Assessment and use of two silicon carbide multi-well plates for library synthesis and proteolytic digests using microwave heating
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The use of two silicon carbide plates is reported for the preparation of three libraries of organic molecules using microwave heating. In addition, a preliminary study has been carried out, showing that one of the plates can also be used in a proteomics setting. Both the 24-position and 48-position plates heated evenly when irradiated with microwave energy. The 48-position plate was used to prepare a library of N-aryl functionalized β-amino esters via an aza-Michael reaction between anilines and Michael acceptors. The 24-position plate was used to prepare a library of biaryls via a Suzuki coupling methodology and a library of 1,4-dihydropyridines via a Hantzsch synthesis. The 48-position plate was also used to perform the proteolytic digestion of insulin chain B by trypsin. The Royal Society of Chemistry 2009.
- Stencel, Lauren M.,Kormos, Chad M.,Avery, Keri B.,Leadbeater, Nicholas E.
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experimental part
p. 2452 - 2457
(2009/09/26)
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- Cu(OTf)2 Catalyzed high yield synthesis of Hantzsch 1,4-dihydropyridines
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Copper(II) triflate catalyzes efficiently the three-component condensation of aldehydes, β-ketoesters and ammonium acetate in acetonitrile at 25°C to afford the corresponding Hantzsch 1,4-dihydropyridines in high yields.
- Paraskar, Abhimanyu S.,Sudalai, Arumugam
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p. 331 - 335
(2008/02/09)
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- One-pot synthesis and aromatization of 1,4-dihydropyridines in refluxing water
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A series of 1,4-dihydropyridines were synthesized in an environmentally benign method, by reacting aldehydes with acetoacetate esters or acetylacetone and ammonium acetate in refluxing water. The thus formed 1,4-dihydropyridines was subsequently oxidized in one-pot to the corresponding pyridine derivatives by either ferric chloride or potassium permanganate. Georg Thieme Verlag Stuttgart.
- Xia, Jing-Jing,Wang, Guan-Wu
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p. 2379 - 2383
(2007/10/03)
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- PROCESS FOR THE PREPARATION OF 1,4-DIHYDROPYRIDINES AND NOVEL 1,4-DIHYDROPYRIDINES USEFUL AS THERAPEUTIC AGENTS
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The present invention provides a process for the preparation of 1,4-dihydropyridines of the formula (1), wherein R1 is H, NO2, Cl, OAc, OH, R2 is H, NO2, Cl, -O-CH2-O-, OMe, OAc, OEt, OH, R3 is H, NO2, Cl, N(Me)2, -O- CH2 -O-, OMe, OAc, OH, R4 is H, OMe, OAc, OH, R5 is H, Cl, I, and R6 and R7 are either methyl, ethyl or both by preparing a mixture of an aromatic aldehyde, alkyl acetoacetate and a source of ammonia, adsorbing the prepared mixture and adsorbent till adsorbent becomes free flowing, heating the material so obtained under microwave irradiation, cooling the reaction mixture and recovering the compound of formula (1). The present invention also relates to novel 1,4-dihydropyridines with cardiovascular activity.
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