Department of Medicinal Chemistry, National Institution of Pharmaceutical Education and Research (NIPER), Hyderabad, 500037, India.
ChemMedChem. 2022 Apr 20;17(8):e202100736. doi: 10.1002/cmdc.202100736. Epub 2022 Mar 15.
Knoevenagel condensation is an entrenched, prevailing, prominent arsenal following greener principles in the generation of α, β-unsaturated ketones/carboxylic acids by involving carbonyl functionalities and active methylenes. This reaction has proved to be a major driving force in many multicomponent reactions indicating the prolific utility toward the development of biologically fascinating molecules. This eminent reaction was acclimatised on different pharmacophoric aldehydes (benzimidazole, β-carboline, phenanthrene, indole, imidazothiadiazole, pyrazole etc.) and active methylenes (oxindole, barbituric acid, Meldrum's acid, thiazolidinedione etc.) to generate the library of chemical compounds. Their potential was also explicit to understand the significance of functionalities involved, which thereby evoke further developments in drug discovery. Furthermore, most of these reaction products exhibited remarkable anticancer activity in nanomolar to micromolar ranges by targeting different cancer targets like DNA, microtubules, Topo-I/II, and kinases (PIM, PARP, NMP, p300/CBP) etc. This review underscores the efficiency of the Knoevenagel condensation explored in the past six-year to generate molecules of pharmacological interest, predominantly toward cancer. The present review also provides the aspects of structure-activity relationships, mode of action and docking study with possible interaction with the target protein.
Knoevenagel 缩合反应是一种在涉及羰基官能团和活性亚甲基时生成α,β-不饱和酮/羧酸的绿色原则下被广泛应用的方法,它是许多多组分反应中的主要驱动力,表明其在开发具有生物吸引力的分子方面具有广泛的用途。该反应已适应于不同的药效团醛(苯并咪唑、β-咔啉、菲、吲哚、咪唑噻二唑、吡唑等)和活性亚甲基(色酮、巴比妥酸、Meldrum 酸、噻唑烷二酮等),以生成化合物库。它们的潜力也很明显,可以了解所涉及的功能的意义,从而引发药物发现的进一步发展。此外,这些反应产物中的大多数通过针对不同的癌症靶点(如 DNA、微管、Topo-I/II 和激酶(PIM、PARP、NMP、p300/CBP)等),在纳摩尔到微摩尔范围内表现出显著的抗癌活性。这篇综述强调了过去六年中 Knoevenagel 缩合反应在生成具有药理兴趣的分子方面的效率,主要针对癌症。本综述还提供了构效关系、作用机制和对接研究的方面,以及与靶蛋白的可能相互作用。