Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazolesd

被引：74

作者：

Taha, Muhammad ^{[1
,2
]}

Ismail, Nor Hadiani ^{[1
,2
]}

Imran, Syahrul ^{[1
,2
]}

Wadood, Abdul ^{[3
]}

Rahim, Fazal ^{[4
]}

Saad, Syed Muhammad ^{[5
]}

Khan, Khalid Mohammed ^{[5
]}

Nasir, Abdul ^{[3
]}

机构：

[1] Univ Teknol MARA UiTM, Atta Ur Rahman Inst Nat Prod Discovery, Puncak Alam Campus, Bandar Puncak Alam 42300, Selangor, Malaysia

[2] Univ Teknol MARA UiTM, Fac Sci Appl, Shah Alam 40450, Selangor, Malaysia

[3] Abdul Wali Khan Univ, Dept Biochem, Computat Med Chem Lab, Mardan 23200, Mardan, Pakistan

[4] Hazara Univ, Dept Chem, Mansehra 21300, Pakistan

[5] Univ Karachi, Int Ctr Chem & Biol Sci, HEJ Res Inst Chem, Karachi 75270, Pakistan

来源：

BIOORGANIC CHEMISTRY | 2016年 / 66卷

关键词：

1,3,4-Oxadiazole; alpha-Glucosidase inhibition; Structure-activity relationship; Molecular docking; BIOLOGICAL-ACTIVITY; DERIVATIVES; POTENT; DISCOVERY; REPLACEMENTS; ANALOGS; DESIGN; AGENTS; AIDS;

D O I：

10.1016/j.bioorg.2016.04.006

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：

Twenty derivatives of 5-aryl-2-(6'-nitrobenzofuran-2'-yl)-1,3,4-oxadiazoles (1-20) were synthesized and evaluated for their alpha-glucosidase inhibitory activities. Compounds containing hydroxyl and halogens (1-6, and 8-18) were found to be five to seventy folds more active with IC50 values in the range of 12.75 +/- 0.10-162.05 +/- 1.65 mu M, in comparison with the standard drug, acarbose (IC50 = 856.45 +/- 5.60 mu M). Current study explores the alpha-glucosidase inhibition of a hybrid class of compounds of oxadiazole and benzofurans. These findings may invite researchers to work in the area of treatment of hyperglycemia. Docking studies showed that most compounds are interacting with important amino acids Glu 276, Asp 214 and Phe 177 through hydrogen bonds and arene-arene interaction. (C) 2016 Elsevier Inc. All rights reserved.

引用

页码：117 / 123

页数：7

共 39 条

[1] Amir M, 1998, INDIAN J HETEROCY CH, V8, P107
[2] BISCHOFF H, 1994, EUR J CLIN INVEST, V24, P3
[3] Alpha glucosidase inhibition by stem extract of Tinospora cordifolia
Chougale, Ashok D.
Ghadyale, Varsha A.
Panaskar, Shrimant N.
Arvindekar, Akalpita U.
[J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2009, 24 (04) : 998 - 1001
[4] DABHI T P, 1992, Indian Journal of Pharmaceutical Sciences, V54, P98
[5] α- and β-Glucosidase inhibitors:: chemical structure and biological activity
de Melo, Eduardo Borges
Gomes, Adriane da Silveira
Carvalho, Ivone
[J]. TETRAHEDRON, 2006, 62 (44) : 10277 - 10302
[6] Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000-2012
de Oliveira, Cledualdo Soares
Lira, Bruno Freitas
Barbosa-Filho, Jose Maria
Fernandez Lorenzo, Jorge Goncalo
de Athayde-Filho, Petronio Filgueiras
[J]. MOLECULES, 2012, 17 (09) : 10192 - 10231
[7] Synthesis, Biological Activity, and Molecular Modeling Studies of 1H-1,2,3-Triazole Derivatives of Carbohydrates as α-Glucosidases Inhibitors
Ferreira, Sabrina B.
Sodero, Ana C. R.
Cardoso, Mariana F. C.
Lima, Emerson S.
Kaiser, Carlos R.
Silva, Floriano P., Jr.
Ferreira, Vitor F.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (06) : 2364 - 2375
[8] Synthesis of new nitrogen analogues of salacinol and deoxynojirimycin and their evaluation as glycosidase inhibitors
Gallienne, E
Gefflaut, T
Bolte, J
Lemaire, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03) : 894 - 902
[9] GOSWAMI BN, 1984, INDIAN J CHEM B, V23, P796
[10] GROOPMAN JE, 1990, REV INFECT DIS, V12, P908

← 1 2 3 4 →