Green approach for synthesis of bioactive Hantzsch 1,4-dihydropyridine derivatives based on thiophene moiety via multicomponent reaction

Abstract

A novel green and efficient one-pot multicomponent reaction of dihydropyridine derivatives was reported as having good to excellent yield. In the presence of the catalyst ceric ammonium nitrate (CAN), different 1,3-diones and same starting materials as 5-bromothiophene-2-carboxaldehyde and ammonium acetate were used at room temperature under solvent-free condition for the Hantzsch pyridine synthesis within a short period of time. All compounds were evaluated for their in vitro antibacterial and antifungal activity and, interestingly, we found that 5(b–f) show excellent activity compared with Ampicillin, whereas only the 5e compound shows excellent antifungal activity against Candida albicans compared with griseofulvin. The cytotoxicity of all compounds has been assessed against breast tumour cell lines (BT-549), but no activity was found. The X-ray structure of one such compound, 5a, viewed as a colourless block crystal, corresponded accurately to a primitive monoclinic cell.

Impact of an aryl bulky group on a one-pot reaction of aldehyde with malononitrile and N-substituted 2-cyanoacetamide

“…We performed this reaction via a one-pot strategy, which has been reported in many reactions, [5][6][7][8] because it has certain advantages based on green chemistry concepts such as the reduction of chemical waste, workup procedure, purication process, and time, which make the reaction greener. 9 In the literature, the one-pot reaction of aryl aldehyde, malononitrile and N-substituted 2-cyanoacetamide is mostly reported to use piperidine [10][11][12] as a catalyst.…”

Evaluation of the antioxidant activities of fatty polyhydroquinolines synthesized by Hantzsch multicomponent reactions

“…3 1,4-Dihydropyridines, also called 1,4-DHPs or Hantzsch compounds, are important precursors due to their pharmacological and biological (e.g., antihypertensive and anti-anginal) activities as well as the ability to aid calcium channel blockade, thereby reducing the risk of cardiovascular diseases. 4 The 1,4-DHP scaffold serves as a nucleus for several commercial drugs such as nifedipine (1st generation), felodipine and nitrendipine (2nd generation), and amlodipine (3rd generation) ( Fig. 1).…”

A one‐pot multicomponent Biginelli reaction for the preparation of novel pyrimidinthione derivatives as antimicrobial agents

“…Pyrimidinthione derivatives are very important in pharmaceutical and medicinal chemistry as they showed wide range of biological activities. [13][14][15][16] Biginelli reaction is very popular for the synthesis of these compounds and was first published in 1891 by the use of three components. Moreover, it is also expecting from chemists to synthesize compounds by the green and environment friendly approaches.…”

“…Moreover, it is also expecting from chemists to synthesize compounds by the green and environment friendly approaches. [13][14][15][16] Biginelli reaction is very popular for the synthesis of these compounds and was first published in 1891 by the use of three components. [17] Since then it is widely used to synthesize pyrimidinthiones.…”