Abstract

The present work deals with a comparative experimental and theoretical study on a synthetic analog of biologically relevant 4H-pyran motif. We have performed spectral and structural properties of 6-amino-3-phenyl-4-(pyridin-4-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile. This compound was synthesized in 89% yield by following a simple, straightforward, and highly efficient multicomponent one-pot protocol under the excellent catalytic influence of nontoxic trisodium citrate dihydrate at ambient conditions. The quantum chemical computations of the vibrational frequencies were carried out using the Gaussian 09 program followed by the full optimizations done using density functional theory (DFT) at B3LYP/6-311 + G(d,p) level. The optimized structure, vibrational, and NMR spectra are in good agreement with the experimental data. The combined use of experimental and computational work allowed a firm assignment of the majority of observed bands for the compound. The molecular docking study has been utilized to explore the binding modes of the compound to the target enzyme multidrug resistance protein. This result suggests the pharmaceutical importance of the titled compound in the field of drug discovery.

摘要

目前的工作涉及对生物学相关的 4 H-吡喃基序的合成类似物的比较实验和理论研究。我们已经完成了 6-amino-3-phenyl-4-(pyridin-4-yl)-2,4-dihydropyrano[2,3- c]吡唑-5-甲腈。在环境条件下无毒柠檬酸三钠二水合物的优异催化作用下，按照简单、直接、高效的多组分一锅法合成该化合物，收率 89%。使用 Gaussian 09 程序进行振动频率的量子化学计算，然后使用 B3LYP/6-311 + G(d,p) 水平的密度泛函理论 (DFT) 进行全面优化。优化后的结构、振动和核磁共振谱与实验数据吻合良好。实验和计算工作的结合使用可以确定化合物的大多数观察带。分子对接研究已被用于探索该化合物与靶酶多药耐药蛋白的结合模式。该结果表明标题化合物在药物发现领域的药学重要性。