Synthesis, crystal structure, DFT, α-glucosidase and α-amylase inhibition and molecular docking studies of (E)- N′-(4-chlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide

被引：47

作者：

Karrouchi, Khalid ^{[1
]}

Fettach, Saad ^{[2
]}

Anouar, El Hassane ^{[3
]}

Tuzun, Burak ^{[4
]}

Radi, Smaail ^{[5
]}

Alharthi, Abdulrahman I. ^{[3
]}

Ghabbour, Hazem A. ^{[6
]}

Mabkhot, Yahia N. ^{[7
]}

Faouzi, My El Abbes ^{[2
]}

Ansar, M'hammed ^{[8
]}

Garcia, Yann ^{[9
]}

机构：

[1] Mohammed V Univ Rabat, Fac Med & Pharm, Lab Analyt Chem & Bromatol, Rabat, Morocco

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

[3] Prince Sattam bin Abdulaziz Univ, Coll Sci & Humanities Al Kharj, Dept Chem, Al Kharj 11942, Saudi Arabia

[4] Cumhuriyet Univ, Dept Chem, Sci Fac, TR-58140 Sivas, Turkey

[5] Univ Mohammed 1, Fac Sci, Lab Chim Appl & Environm LCAE, Oujda 60000, Morocco

[6] Univ Mansoura, Fac Pharm, Dept Med Chem, Mansoura 35516, Egypt

[7] King Khalid Univ, Coll Pharm, Dept Pharmaceut Chem, POB 960, Abha 61421, Saudi Arabia

[8] Mohammed V Univ Rabat, Fac Med & Pharm, Lab Med Chem, Rabat, Morocco

[9] Catholic Univ Louvain, Inst Condensed Matter & Nanosci Mol Chem Mat & Ca, Pl L Pasteur 1, B-1348 Louvain La Neuve, Belgium

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2021年 / 1245卷

关键词：

Pyrazole; Crystal structure; DFT calculations; alpha-glucosidase; alpha-amylase; Molecular docking; SCHIFF-BASES; PYRAZOLE; DERIVATIVES; ANTIOXIDANT; COMPLEXES; CO(II);

D O I：

10.1016/j.molstruc.2021.131067

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

In this work, a novel crystal i.e. (E)-N'-(4-chlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide has been synthesized and characterized using various spectroscopic techniques. The (E)-configuration of the azomethine (N=CH) was confirmed by single crystal X-ray analysis. The molecule crystallizes in the monoclinic space group, P21/c, a = 15.629(9) angstrom, b = 7.152(4) angstrom, c = 14.707(9) angstrom, beta = 111.061(15)degrees, V = 1534.1(6) angstrom(3) and Z = 4. In addition, the elucidated molecular structure was confirmed by comparing the predicted Z-matrix geometries and spectroscopic data with the experimental ones. DFT calculations have been carried out in gas and IEFPCM solvent at the B3LYP/6-31+G(d,p). The in vitro anti-diabetic potential of the title compound was evaluated against alpha-glucosidase and alpha-amylase enzymes. Molecular docking studies showed that the various interactions tightly anchored the title compound to the active site, which makes it a more potent alpha-glucosidase inhibitor compared to well-known Acarbose. (C) 2021 Elsevier B.V. All rights reserved.

引用

页数：10