Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles

CuSO4/hydrazine hydrate was used as a catalyst system for copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) of AZT and 5′-azido adenosine with terminal alkynes to give 30 novel 1,2,3-triazole derivatives. Screening for their anticancer, anti-inflammatory, angiotensin-converting enzyme 2 (ACE2),...

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Bibliographic Details
Published in:Journal of chemistry 2023-09, Vol.2023, p.1-17
Main Authors: Le, Duc Anh, Truong, Ngoc Hung, Vu, Van Dung, Doan, Thanh Huyen, Le, Minh Tri, Nguyen, Thi Huong, Nguyen, Manh Cuong, Do, Huu Nghi, Ninh, Duc Bao, Le, Phong, Nguyen, Thi Phuong Thao, Tran, Khac Vu, Luu, Van Chinh
Format: Article
Language:English
Subjects:
Acids
Adenosine
Alkynes
Biological activity
Cancer
Carbon
Chemistry
Copper
Cycloaddition
Cytotoxicity
Ethylenediaminetetraacetic acid
Hydrazines
Proteases
Severe acute respiratory syndrome coronavirus 2
Triazoles
Zidovudine
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Summary:CuSO4/hydrazine hydrate was used as a catalyst system for copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) of AZT and 5′-azido adenosine with terminal alkynes to give 30 novel 1,2,3-triazole derivatives. Screening for their anticancer, anti-inflammatory, angiotensin-converting enzyme 2 (ACE2), and 3C-like protease (3CLpro) inhibitory activities showed that several triazoles of AZT containing murayafoline A and indirubin-3′-oxime inhibited the growth of HepG2 and LU-1 with the IC50 values ranging from 11.01 to 19.87 μg/mL. Besides that, some triazole derivatives of adenosine exhibited anti-inflammatory activity against RAW264.7 cells with the IC50 values within an interval of 12.00–59.48.00 μg/mL. Especially, two triazoles of adenosine with indirubin-3′-oxime at O- and N1 positions expressed the ACE2 and 3CLpro inhibitory activities in which the triazole of adenosine with indirubin-3′-oxime at N1 inhibited both ACE2 and 3CLpro inhibitory activities with IC50 values of 135.62 and 142.95 μg/mL, respectively.
ISSN:2090-9063
2090-9071
DOI:10.1155/2023/1605316