Synthesis and biological evaluation of new pyridines containing imidazole moiety as antimicrobial and anticancer agents

Abstract

The synthesis of a novel series of pyridine and bipyridine derivatives is described via one-pot multicomponent reaction of 5-acetylimidazole, malonitrile (or ethylcyanoacetate or diethylmalonate), substituted benzaldehyde (or terephthaldehyde), and ammonium acetate in good yields. The structures of all the new compounds were elucidated on the basis of elemental analysis and spectral data. The antimicrobial activities of the synthesized compounds were screened and the results showed that most of such compounds exhibit considerable activities. Furthermore, some of the newly synthesized compounds were screened for their anticancer activity against human breast cell line (MCF-7) and liver carcinoma cell line (HEPG2) in comparison to doxorubicin. Most of the tested compounds exhibited promising activity.

Recent Progress on Nicotinonitrile Scaffold‐based Anticancer, Antitumor, and Antimicrobial Agents: A Literature Review

“…synthesized a series of 3‐cyanopyridine derivatives 141a – f via one‐pot condensation reaction of acetylimidazole 139 , aldehyde 140a – f , malononitrile, and ammonium acetate in refluxing acetic acid (Scheme ). In a similar manner, condensation of acetylimidazole 139 with the appropriate aromatic aldehydes 140a – f and ethyl cyanoacetate and ammonium acetate in acetic acid gave the corresponding cyanopyridones 142a – f (Scheme ) .…”

“…Doxorubicin and vinblastine sulfate were used as reference drugs. The results revealed that most of the tested compounds exhibited promising activity . Furthermore, the antimicrobial activities of the synthesized compounds 441a – f and 142a – f were screened, and the results showed that most of such compounds exhibit considerable activities .…”

“…The glycosides 161a , b , riboside 166 , xyloside 167 , and lactoside 171 were deacetylated via Et 3 N, MeOH, and water to produce 162a , b and 172 (Schemes and ) . The in vitro growth inhibitory activities of 161a , b , 162a , 166 , 167 , 169 , and 171 against MCF‐7 cell lines displayed significant antitumor activity.…”

Synthesis of some new Pyridine‐based Heterocyclic Compounds with Anticipated Antitumor Activity

“…Identification of novel structure leads that may be of use in designing new, potent, selective, and less toxic anticancer agents remains a major challenge for medicinal chemistry researchers. The pyridine nucleus is a key constituent, present in a range of bioactive compounds, occurring both synthetically and naturally with wide range of biological applications . Among the successful examples as drug, candidates possessing pyridine nucleus are streptonigrin, streptonigrone, and lavendamycin that are described in the literature as anticancer drugs.…”

An Efficient Synthesis of Novel Pyrazole-Based Heterocycles as Potential Antitumor Agents

“…Many pyrazole-derived compounds are known to exhibit anticancer [6][7][8][9][10], antimicrobial [11,12], antiviral [13], antiparasitic [14], anti-inflammatory [15,16], antipyretic [17], analgesic [18], anticoagulant [19], and anti-obesity [20] biological activities. The pyridine nucleus is a key constituent, present in a range of bioactive compounds, occurring both synthetically and naturally with wide range of biological applications [21,22]. Among the successful examples as drug candidates possessing pyridine nuclei are streptonigrin, streptonigrone, and lavendamycin, which are described in the literature as anticancer drugs.…”