10354-29-7Relevant articles and documents
Hantzsch 1,4-dihydropyridine synthesis in aqueous ethanol by visible light
Ghosh, Somnath,Saikh, Forid,Das, Jhantu,Pramanik, Arun Kumar
, p. 58 - 62 (2013)
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.
Aqua-mediated one-pot synthesis of Biginelli dihydropyrimidinone/thiones (DHPMs), Hantzsch dihydropyridines (DHPs), and polysubstituted pyridines sonocatalyzed by metal-supported nanocatalysts
Safa, Kazem D.,Esmaili, Maryam,Allahvirdinesbat, Maryam
, p. 267 - 277 (2016)
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.
2-Hydroxyethylammonium acetate: An efficient and reusable homogeneous catalyst for the synthesis of Hantzsch 1, 4-dihydropyridines
Kang, Li-Qin,Cao, Zhi-Jun,Lei, Ze-Jun
, p. 1125 - 1128 (2016)
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
Revisiting ageless antiques; synthesis, biological evaluation, docking simulation and mechanistic insights of 1,4-Dihydropyridines as anticancer agents
Sidhom, Peter A.,El-Bastawissy, Eman,Salama, Abeer A.,El-Moselhy, Tarek F.
, (2021)
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.
Silica sulfuric acid: An efficient heterogeneous catalyst for the one-pot synthesis of 1,4-dihydropyridines under mild and solvent-free conditions
Datta, Bandita,Pasha, M. Afzal
, p. 1180 - 1184 (2011)
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.
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
Prasanthi,Prasad,Bharathi
, p. 516 - 525 (2013/10/01)
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-
Synthesis of some new 1,4-dihydropyridine derivatives through a facile one-pot Hantzsch condensation catalyzed by triethylamine
Ghalem, Wassima,Boulcina, Raouf,Debache, Abdelmadjid
experimental part, p. 733 - 737 (2012/05/20)
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.
Silica Sulfuric Acid: An Efficient Heterogeneous Catalyst for the One-Pot Synthesis of 1,4-Dihydropyridines under Mild and Solvent-Free Conditions
Datta, Bandita,Pasha, M. Afzal
, p. 1180 - 1184 (2016/04/10)
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.
Assessment and use of two silicon carbide multi-well plates for library synthesis and proteolytic digests using microwave heating
Stencel, Lauren M.,Kormos, Chad M.,Avery, Keri B.,Leadbeater, Nicholas E.
experimental part, p. 2452 - 2457 (2009/09/26)
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.
Cu(OTf)2 Catalyzed high yield synthesis of Hantzsch 1,4-dihydropyridines
Paraskar, Abhimanyu S.,Sudalai, Arumugam
, p. 331 - 335 (2008/02/09)
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.
