新型抗菌药物3-{(1h -苯并[d]咪唑-2-基)氨基(苯基)甲基}苯并呋喃-2(3H)-的一锅合成及其分子对接研究

IF 3.6 3区 医学 Q2 CHEMISTRY, MEDICINAL
Paras J. Patel, Mehul P. Parmar, Disha P. Vala, Kirti Antil, Subham G. Patel, Shana Balachandran, Divyang M. Patel, Nagesh Kumar Kandukuri, Madan Kumar Arumugam, Rakesh K. Sharma, Hitendra M. Patel
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引用次数: 0

摘要

以2-香豆素酮、芳基醛和2-氨基苯并咪唑为原料,通过一锅反应合成了3-{(1h -苯并咪唑-2-基)氨基](取代苯基)甲基}苯并呋喃-2(3H)-化合物。该反应由三乙胺在80℃的乙腈中催化,产率高达85%。制备液相色谱法成功分离出化合物4b和4c两种异构体,纯度达99.30%。它们的绝对构型为化合物4b的(S, R)和化合物4c的(R, S),用电子圆二色性测定,并通过TD-DFT计算证实。合成的化合物(4a-j)及其对构异构体(4b ', 4b″,4c ', 4c″)对枯草芽孢杆菌、金黄色葡萄球菌、溶蛋白葡萄球菌以及真菌白色念珠菌和黑曲霉的抑菌潜力进行了评价。值得注意的是,化合物4a、4d、4i和4j表现出较好的抗菌活性。分子对接研究进一步证实了这些结果,揭示了较强的受体结合亲和力(−7.5 ~−10.5 kcal/mol),超过了标准药物。这些发现突出了氨基苯并咪唑-香豆素酮缀合物作为有效抗菌剂的潜力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

One-Pot Synthesis of Novel 3-{(1H-Benzo[d]Imidazol-2-yl)Amino(Phenyl)Methyl}Benzofuran-2(3H)-Ones as Antimicrobial Agents and Their Molecular Docking Studies

One-Pot Synthesis of Novel 3-{(1H-Benzo[d]Imidazol-2-yl)Amino(Phenyl)Methyl}Benzofuran-2(3H)-Ones as Antimicrobial Agents and Their Molecular Docking Studies

Aminobenzimidazole-coumaranone conjugates, specifically 3-{[(1H-benzo[d]imidazol-2-yl)amino](substitutedphenyl)methyl}benzofuran-2(3H)-ones, were synthesized through a one-pot reaction involving 2-coumaranone, aryl aldehydes, and 2-aminobenzimidazole. This reaction, catalyzed by triethylamine in acetonitrile at 80°C, achieved yields of up to 85%. Preparative liquid chromatography successfully isolated compounds 4b and 4c as two isomers with purities reaching 99.30%. Their absolute configurations, (S, R) for compound 4b and (R, S) for compound 4c, were determined using electronic circular dichroism and confirmed via TD-DFT calculations. The antimicrobial potential of the synthesized compounds (4a–j) and their enantiopure isomers (4b′, 4b″, 4c′, 4c″) was evaluated against the bacterial strains Bacillus subtilis, Staphylococcus aureus, Staphylococcus proteolyticus, and the fungal strains Candida albicans and Aspergillus niger. Notably, compounds 4a, 4d, 4i, and 4j exhibited superior antimicrobial activity. Molecular docking studies further reinforced these results, revealing strong receptor binding affinities (−7.5 to −10.5 kcal/mol), which surpass those of standard drugs. These findings highlight the promising potential of aminobenzimidazole-coumaranone conjugates as effective antimicrobial agents.

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来源期刊
Archiv der Pharmazie
Archiv der Pharmazie 医学-化学综合
CiteScore
7.90
自引率
5.90%
发文量
176
审稿时长
3.0 months
期刊介绍: Archiv der Pharmazie - Chemistry in Life Sciences is an international journal devoted to research and development in all fields of pharmaceutical and medicinal chemistry. Emphasis is put on papers combining synthetic organic chemistry, structural biology, molecular modelling, bioorganic chemistry, natural products chemistry, biochemistry or analytical methods with pharmaceutical or medicinal aspects such as biological activity. The focus of this journal is put on original research papers, but other scientifically valuable contributions (e.g. reviews, minireviews, highlights, symposia contributions, discussions, and essays) are also welcome.
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