Structural elucidation, molecular docking, α-amylase and α-glucosidase inhibition studies of 5-amino-nicotinic acid derivatives

Springer Science and Business Media LLC - Tập 14 Số 1 - 2020
Muhammad Nawaz1, Muhammad Taha2, Faiza Qureshi3, Nisar Ullah4, Manikandan Selvaraj5, Sumaira Shahzad6, Sridevi Chigurupati7, Abdul Waheed4, Fadiah Ammar Almutairi7
1Department of Nano-Medicine Research, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia
2Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia
3Deanship of Scientific Research, Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam, 31441, Saudi Arabia
4Chemistry Department, King Fahd University of Petroleum & Minerals, Dhahran 31261, Saudi Arabia
5School of Chemical Engineering, Monash University, Bandar Subway, 47500, Selangor Darul Ehsan, Malaysia
6School of Business Administration, College of International Education, Zhejiang Gongshang University, Hangzhou, China
7Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraidah, 52571, Saudi Arabia

Tóm tắt

Abstract

In this study, 5-amino-nicotinic acid derivatives (1–13) have been designed and synthesized to evaluate their inhibitory potential against α-amylase and α-glucosidase enzymes. The synthesized compounds (1–13) exhibited promising α-amylase and α-glucosidase activities. IC50 values for α-amylase activity ranged between 12.17 ± 0.14 to 37.33 ± 0.02 µg/mL ± SEM while for α-glucosidase activity the IC50 values were ranged between 12.01 ± 0.09 to 38.01 ± 0.12 µg/mL ± SEM. In particular, compounds 2 and 4–8 demonstrated significant inhibitory activities against α-amylase and α-glucosidase and the inhibitory potential of these compounds was comparable to the standard acarbose (10.98 ± 0.03 and 10.79 ± 0.17 µg/mL ± SEM, respectively). In addition, the impact of substituent on the inhibitory potential of these compounds was assessed to establish structure activity relationships. Studies in molecular simulations were conducted to better comprehend the binding properties of the compounds. All the synthesized compounds were extensively characterized with modern spectroscopic methods including 1H-NMR, 13C–NMR, FTIR, HR-MS and elemental analysis.

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