Synthesis of thymidine phosphorylase inhibitor based on quinoxaline derivatives and their molecular docking study

Noor Barak, Almandil and Taha, Muhammad and Farooq, Rai Khalid and Alhibshi, Amani and Ibrahim, Mohamed and Anouar, El Hassane and Gollapalli, Mohammed and Rahim, Fazal and Nawaz, Muhammad and ,, Syed Adnan Ali Shah and Ahmed, Qamar Uddin and Zakaria, Zainul Amiruddin (2019) Synthesis of thymidine phosphorylase inhibitor based on quinoxaline derivatives and their molecular docking study. Molecules, 24 (6). pp. 1-18. ISSN 1420-3049

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Abstract

We have synthesized quinoxaline analogs (1–25), characterized by 1H-NMR and HREI-MS and evaluated for thymidine phosphorylase inhibition. Among the series, nineteen analogs showed better inhibition when compared with the standard inhibitor 7-Deazaxanthine (IC50 = 38.68 ± 4.42 µM). The most potent compound among the series is analog 25 with IC50 value 3.20 ± 0.10 µM. Sixteen analogs 1, 2, 3, 4, 5, 6, 7, 12, 13, 14, 15, 16, 17, 18, 21 and 24 showed outstanding inhibition which is many folds better than the standard 7-Deazaxanthine. Two analogs 8 and 9 showed moderate inhibition. A structure-activity relationship has been established mainly based upon the substitution pattern on the phenyl ring. The binding interactions of the active compounds were confirmed through molecular docking studies.

Item Type:	Article (Journal)
Additional Information:	4921/72692
Uncontrolled Keywords:	quinoxaline analogs; synthesis; thymidine phosphorylase inhibition; molecular docking
Subjects:	R Medicine > RS Pharmacy and materia medica
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Pharmacy Kulliyyah of Pharmacy > Department of Pharmaceutical Chemistry
Depositing User:	Dr Qamar Uddin Ahmed
Date Deposited:	18 Jun 2019 11:15
Last Modified:	01 Aug 2019 11:05
URI:	http://irep.iium.edu.my/id/eprint/72692

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