Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives

Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives

We have synthesized oxadiazole derivatives (1–16), characterized by 1H NMR, 13C NMR and HREI-MS and screened for thymidine phosphorylase inhibitory potential. All derivatives display varied degree of thymidine phosphorylase inhibition in the range of 1.10 ± 0.05 to 49.60 ± 1.30 μM when compared with...

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Published in:Bioorganic Chemistry
Main Author: Ullah H.; Rahim F.; Taha M.; Uddin I.; Wadood A.; Shah S.A.A.; Farooq R.K.; Nawaz M.; Wahab Z.; Khan K.M.
Format: Article
Language:English
Published: Academic Press Inc. 2018
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85043523886&doi=10.1016%2fj.bioorg.2018.02.020&partnerID=40&md5=deb0fe7a6b48ad3f0a96201fc44143e2
id 2-s2.0-85043523886
spelling 2-s2.0-85043523886
Ullah H.; Rahim F.; Taha M.; Uddin I.; Wadood A.; Shah S.A.A.; Farooq R.K.; Nawaz M.; Wahab Z.; Khan K.M.
Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives
2018
Bioorganic Chemistry
78

10.1016/j.bioorg.2018.02.020
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85043523886&doi=10.1016%2fj.bioorg.2018.02.020&partnerID=40&md5=deb0fe7a6b48ad3f0a96201fc44143e2
We have synthesized oxadiazole derivatives (1–16), characterized by 1H NMR, 13C NMR and HREI-MS and screened for thymidine phosphorylase inhibitory potential. All derivatives display varied degree of thymidine phosphorylase inhibition in the range of 1.10 ± 0.05 to 49.60 ± 1.30 μM when compared with the standard inhibitor 7-Deazaxanthine having an IC50 value 38.68 ± 1.12 μM. Structure activity relationships (SAR) has been established for all compounds to explore the role of substitution and nature of functional group attached to the phenyl ring which applies imperious effect on thymidine phosphorylase activity. Molecular docking study was performed to understand the binding interaction of the most active derivatives with enzyme active site. © 2018 Elsevier Inc.
Academic Press Inc.
452068
English
Article
author Ullah H.; Rahim F.; Taha M.; Uddin I.; Wadood A.; Shah S.A.A.; Farooq R.K.; Nawaz M.; Wahab Z.; Khan K.M.
spellingShingle Ullah H.; Rahim F.; Taha M.; Uddin I.; Wadood A.; Shah S.A.A.; Farooq R.K.; Nawaz M.; Wahab Z.; Khan K.M.
Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives
author_facet Ullah H.; Rahim F.; Taha M.; Uddin I.; Wadood A.; Shah S.A.A.; Farooq R.K.; Nawaz M.; Wahab Z.; Khan K.M.
author_sort Ullah H.; Rahim F.; Taha M.; Uddin I.; Wadood A.; Shah S.A.A.; Farooq R.K.; Nawaz M.; Wahab Z.; Khan K.M.
title Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives
title_short Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives
title_full Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives
title_fullStr Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives
title_full_unstemmed Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives
title_sort Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives
publishDate 2018
container_title Bioorganic Chemistry
container_volume 78
container_issue
doi_str_mv 10.1016/j.bioorg.2018.02.020
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85043523886&doi=10.1016%2fj.bioorg.2018.02.020&partnerID=40&md5=deb0fe7a6b48ad3f0a96201fc44143e2
description We have synthesized oxadiazole derivatives (1–16), characterized by 1H NMR, 13C NMR and HREI-MS and screened for thymidine phosphorylase inhibitory potential. All derivatives display varied degree of thymidine phosphorylase inhibition in the range of 1.10 ± 0.05 to 49.60 ± 1.30 μM when compared with the standard inhibitor 7-Deazaxanthine having an IC50 value 38.68 ± 1.12 μM. Structure activity relationships (SAR) has been established for all compounds to explore the role of substitution and nature of functional group attached to the phenyl ring which applies imperious effect on thymidine phosphorylase activity. Molecular docking study was performed to understand the binding interaction of the most active derivatives with enzyme active site. © 2018 Elsevier Inc.
publisher Academic Press Inc.
issn 452068
language English
format Article
accesstype
record_format scopus
collection Scopus
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