Aryl-oxadiazole Schiff bases: Synthesis, α-glucosidase in vitro inhibitory activity and their in silico studies

被引：39

作者：

Ullah, Hayat ^{[1
]}

Rahim, Fazal ^{[1
]}

Taha, Muhammad ^{[2
]}

Hussain, Raffaqat ^{[1
]}

Tabassum, Nida ^{[3
]}

Wadood, Abdul ^{[4
]}

Nawaz, Mohsan ^{[1
]}

Mosaddik, Ashik ^{[5
]}

Imran, Syahrul ^{[5
]}

Wahab, Zainul ^{[6
]}

Miana, Ghulam Abbas ^{[7
,8
]}

Kanwal ^{[7
]}

Khan, Khalid Mohammed ^{[2
,7
]}

机构：

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

[2] Imam Abdulrahman Bin Faisal Univ, IRMC, Dept Clin Pharm, POB 31441, Dammam, Saudi Arabia

[3] Rawalpindi Med Coll, Dept Pharmacol, Rawalpindi 46300, Pakistan

[4] Abdul Wali Khan Univ Mardan, Dept Biochem, Mardan 23200, Pakistan

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

[6] Hazara Univ, Dept Conservat Sci, Mansehra 21300, Pakistan

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

[8] Riphah Int Univ, Riphah Inst Pharmaceut Sci, 7th Ave,G-7-4, Islamabad, Pakistan

来源：

ARABIAN JOURNAL OF CHEMISTRY | 2020年 / 13卷 / 04期

关键词：

Synthesis; Aryl-oxadiazole Schiff bases; alpha-glucosidase; Molecular docking; Structure-activity relationship (SAR); MOLECULAR DOCKING; ANTIINFLAMMATORY ACTIVITY; BIOLOGICAL EVALUATION; DERIVATIVES; POTENT; 1,3,4-OXADIAZOLE; ANALOGS; DESIGN; ACETYLCHOLINESTERASE; ETHER;

D O I：

10.1016/j.arabjc.2020.01.005

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-Glucosidase enzyme is a therapeutic target for diabetes mellitus and its inhibitors play a vital role in the treatment of this disease. A new series of aryl-oxadiazole Schiff bases (1-18) were synthesized and evaluated for alpha-glucosidase inhibitory potential. Fifteen compounds 1-8, 11-13, and 15-18 showed excellent inhibition with IC50 values ranging from 0.30 +/- 0.2 to 35.1 +/- 0.80 mu M as compared to the standard inhibitor acarbose (IC50 = 38.45 +/- 0.80 mu M), nonetheless, the remaining compounds were found to have moderate activity. Among the series, compounds 7 (IC50= 0.30 +/- 0.2 mu M) with hydroxy groups at phenyl rings on either side of the oxadiazole ring was identified as the most potent inhibitor of alpha-glucosidase. The molecular docking studies were conducted to understand the binding mode of active inhibitors with the active site of enzyme and results supported the experimental data. (C) 2020 Published by Elsevier B.V. on behalf of King Saud University.

引用

页码：4904 / 4915

页数：12

共 39 条

[1] α-glucosidase inhibitors prevent diet-induced increases in intestinal sugar transport in diabetic mice
Casirola, Donatella M.
Ferraris, Ronaldo P.
[J]. METABOLISM-CLINICAL AND EXPERIMENTAL, 2006, 55 (06): : 832 - 841
[2] Acarbose treatment and the risk of cardiovascular disease and hypertension in patients with impaired glucose tolerance - The STOP-NIDDM Ttrial
Chiasson, JL
Josse, RG
Gomis, R
Hanefeld, M
Karasik, A
Laakso, M
[J]. JAMA-JOURNAL OF THE AMERICAN MEDICAL ASSOCIATION, 2003, 290 (04): : 486 - 494
[3] Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities
Dogan, HN
Duran, A
Rollas, S
Sener, G
Uysal, MK
Gülen, D
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (09) : 2893 - 2898
[4] Efficient One-Pot Synthesis of Benzimidazoles Under Solvent-Free Conditions
Du, Li-Hua
Luo, Xi-Ping
[J]. SYNTHETIC COMMUNICATIONS, 2010, 40 (19) : 2880 - 2886
[5] Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(I-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones
El-Emam, AA
Al-Deeb, OA
Al-Omar, M
Lehmann, J
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (19) : 5107 - 5113
[6] Ganoderol B: A potent α-glucosidase inhibitor isolated from the fruiting body of Ganoderma lucidum
Fatmawati, Sri
Shimizu, Kuniyoshi
Kondo, Ryuichiro
[J]. PHYTOMEDICINE, 2011, 18 (12) : 1053 - 1055
[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] Holla BS, 2005, INDIAN J CHEM B, V44, P1669
[9] Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones as safer antiinflammatory and analgesic agents
Husain, Asif
Ahmad, Ausaf
Alam, M. M.
Ajmal, Mohd.
Ahuja, Priyanka
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (09) : 3798 - 3804
[10] Voglibose for prevention of type 2 diabetes mellitus: a randomised, double-blind trial in Japanese individuals with impaired glucose tolerance
Kawamori, Ryuzo
Tajima, Naoko
Iwamoto, Yasuhiko
Kashiwagi, Atsunori
Shimamoto, Kazuaki
Koku, Kohei
[J]. LANCET, 2009, 373 (9675) : 1607 - 1614

← 1 2 3 4 →