Synthesis, characterization, X-ray, a-glucosidase inhibition and molecular docking study of new triazolic systems based on 1,5-benzodiazepine via 1,3-dipolar cycloaddition reactions

被引：10

作者：

Ait Lahcen, Marouane ^{[1
]}

Adardour, Mohamed ^{[1
]}

Mortada, Salma ^{[2
]}

Oubahmane, Mehdi ^{[1
]}

Hmaimou, Samir ^{[1
]}

Loughzail, Mohamed ^{[1
]}

Hdoufane, Ismail ^{[1
]}

Lahmidi, Sanae ^{[3
]}

Faouzi, My El Abbes ^{[2
]}

Cherqaoui, Driss ^{[1
]}

Mague, Joel T. ^{[4
]}

Baouid, Abdesselam ^{[1
]}

机构：

[1] Cadi Ayyad Univ, Semlalia Fac Sci, Dept Chem, Mol Chem Lab, Marrakech 2390, Morocco

[2] Mohammed V Univ, Fac Med & Pharm, Lab Pharmacol & Toxicol, Biopharmaceut & Toxicol Anal Res Team, Rabat, Morocco

[3] Mohammed V Univ Rabat, Fac Sci, Ctr Rech Sci Medicaments,URAC 21, Pole Competences Pharmacochim,Lab Chim Organ Heter, Rabat, Morocco

[4] Tulane Univ, Dept Chem, New Orleans, LA USA

来源：

JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS | 2024年 / 42卷 / 04期

关键词：

Benzodiazepines; chemo-regioselective; X-ray; alpha-glucosidase inhibition; molecular docking study; ANTIPROLIFERATIVE ACTIVITY; HETEROCYCLIC-SYSTEMS; ANTITUMOR-ACTIVITY; SCHIFF-BASES; DERIVATIVES; ANTIOXIDANT; HYBRIDS; DESIGN;

D O I：

10.1080/07391102.2023.2203263

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We report in this work a synthesis of novel triazolo[1,5]benzodiazepine derivatives by the 1,3-dipolar cycloaddition reaction of N-aryl-C-ethoxycarbonylnitrilimines with 1,5-benzodiazepines. All the structures of the new compounds were determined from their NMR (H-1 and C-13) and HRMS. Then, X-ray crystallography analysis of compound 4d confirmed the stereochemistry of cycloadducts. The compounds 1, 4a-d, 5a-d, 6c, 7 and 8 were evaluated for their in vitro anti-diabetic activity against a-glucosidase. The compounds 1, 4d, 5a and 5b showed potential inhibitory activities compared to standard acarbose. Additionally, an in silico docking study was conducted to look into the active binding mode of the synthesized compounds within the target enzyme.

引用

页码：1985 / 1998

页数：14

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