Synthesis and antidiabetic evaluation of benzimidazole-tethered 1,2,3-triazoles

被引：67

作者：

Deswal, Laxmi ^{[1
]}

Verma, Vikas ^{[1
]}

Kumar, Devinder ^{[1
]}

Kaushik, Chander P. ^{[1
]}

Kumar, Ashwani ^{[2
]}

Deswal, Yogesh ^{[1
]}

Punia, Suman ^{[1
]}

机构：

[1] Guru Jambheshwar Univ Sci & Technol, Dept Chem, Hisar 125001, Haryana, India

[2] Guru Jambheshwar Univ Sci & Technol, Dept Pharmaceut Sci, Hisar, Haryana, India

来源：

ARCHIV DER PHARMAZIE | 2020年 / 353卷 / 09期

关键词：

1,2,3-triazole; antidiabetic; benzimidazole; docking; alpha-amylase; alpha-glucosidase; ALPHA-GLUCOSIDASE INHIBITORS; BIOLOGICAL EVALUATION; ANTICANCER ACTIVITY; MOLECULAR DOCKING; HIGHLY EFFICIENT; DERIVATIVES; OPTIMIZATION; AMYLASE;

D O I：

10.1002/ardp.202000090

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Some novel benzimidazole-tethered 1,2,3-triazole derivatives (4a-r) were synthesized by a click reaction between 2-substituted 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole and in situ azide. The structures of the synthesized compounds were confirmed by spectroscopic studies (one- and two-dimensional nuclear magnetic resonance, Fourier transform infrared, and high-resolution mass spectra). The synthesized compounds were evaluated for their antidiabetic activity. Compounds4a-rexhibited a good-to-moderate alpha-amylase and alpha-glucosidase inhibitory activity, with IC(50)values ranging from 0.0410 to 0.0916 mu mol/ml and 0.0146 to 0.0732 mu mol/ml, respectively. Compounds4e,4g, and4nwere found to be most active. Furthermore, the binding conformation of the most active compounds was ascertained by docking studies.

引用

页数：12

共 49 条

[1] A novel series of N-acyl substituted indole-linked benzimidazoles and naphthoimidazoles as potential anti inflammatory, anti biofilm and anti microbial agents [J].

Abraham, Rajan ;

Periakaruppan, Prakash ;

Mahendran, Karthikeyan ;

Ramanathan, Murugappan .

MICROBIAL PATHOGENESIS, 2018, 114 :409-413

[2] 2-Aryl benzimidazoles: Synthesis, In vitro α-amylase inhibitory activity, and molecular docking study [J].

Adegboye, Akande Akinsola ;

Khan, Khalid Mohammed ;

Salar, Uzma ;

Aboaba, Sherifat Adeyinka ;

Kanwal ;

Chigurupati, Sridevi ;

Fatima, Itrat ;

Taha, Mohammad ;

Wadood, Abdul ;

Mohammad, Jahidul Isalm ;

Khan, Huma ;

Perveen, Shahnaz .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 150 :248-260

[3]

Ahamed M.R., 2013, Al-Nahrain J. Sci., V16, P77

[4] Synthesis of 1H-1,2,3-triazole derivatives as new α-glucosidase inhibitors and their molecular docking studies [J].

Avula, Satya Kumar ;

Khan, Ajmal ;

Rehman, Najeeb Ur ;

Anwar, Muhammad U. ;

Al-Abri, Zahra ;

Wadood, Abdul ;

Riaz, Muhammad ;

Csuk, Rene ;

Al-Harrasi, Ahmed .

BIOORGANIC CHEMISTRY, 2018, 81 :98-106

[5]

Bakri Y. E., 2018, J MOL MODEL, V24, P179

[6] Toward the estimation of the absolute quality of individual protein structure models [J].

Benkert, Pascal ;

Biasini, Marco ;

Schwede, Torsten .

BIOINFORMATICS, 2011, 27 (03) :343-350

[7] BLAST plus : architecture and applications [J].

Camacho, Christiam ;

Coulouris, George ;

Avagyan, Vahram ;

Ma, Ning ;

Papadopoulos, Jason ;

Bealer, Kevin ;

Madden, Thomas L. .

BMC BIOINFORMATICS, 2009, 10

[8] Synthesis and anticancer activity of novel water soluble benzimidazole carbamates [J].

Cheong, Jae Eun ;

Zaffagni, Michela ;

Chung, Ivy ;

Xu, Yingjie ;

Wang, Yiqiang ;

Jernigan, Finith E. ;

Zetter, Bruce R. ;

Sun, Lijun .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 144 :372-385

[9]

Dai ZC, 2015, ORG BIOMOL CHEM, V13, P477, DOI [10.1039/c4ob01758g, 10.1039/C4OB01758G]

[10]

Dassault Systemes BIOVIA, 2016, Discovery Studio Visualizer

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