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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| Main Authors: | , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2023-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2023/1605316 |
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| author | Duc Anh Le Ngoc Hung Truong Van Dung Vu Thanh Huyen Doan Minh Tri Le Thi Huong Nguyen Manh Cuong Nguyen Huu Nghi Do Duc Bao Ninh Phong Le Thi Phuong Thao Nguyen Khac Vu Tran Van Chinh Luu |
| author_facet | Duc Anh Le Ngoc Hung Truong Van Dung Vu Thanh Huyen Doan Minh Tri Le Thi Huong Nguyen Manh Cuong Nguyen Huu Nghi Do Duc Bao Ninh Phong Le Thi Phuong Thao Nguyen Khac Vu Tran Van Chinh Luu |
| author_sort | Duc Anh Le |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-5a1b5dd3ea3f450c89580e2d71090dd9 |
| institution | Kabale University |
| issn | 2090-9071 |
| language | English |
| publishDate | 2023-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-5a1b5dd3ea3f450c89580e2d71090dd92025-08-20T03:34:57ZengWileyJournal of Chemistry2090-90712023-01-01202310.1155/2023/1605316Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-TriazolesDuc Anh Le0Ngoc Hung Truong1Van Dung Vu2Thanh Huyen Doan3Minh Tri Le4Thi Huong Nguyen5Manh Cuong Nguyen6Huu Nghi Do7Duc Bao Ninh8Phong Le9Thi Phuong Thao Nguyen10Khac Vu Tran11Van Chinh Luu12Institute of Chemistry and MaterialInstitute of Natural Products ChemistryInstitute of Chemistry and MaterialInstitute of Chemistry and MaterialInstitute of Chemistry and MaterialInstitute of Chemistry and MaterialInstitute of Natural Products ChemistryInstitute of Natural Products ChemistryTruman State UniversityInstitute of Forensic SciencesSchool of Chemical EngineeringSchool of Chemical EngineeringInstitute of Natural Products ChemistryCuSO4/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.http://dx.doi.org/10.1155/2023/1605316 |
| spellingShingle | Duc Anh Le Ngoc Hung Truong Van Dung Vu Thanh Huyen Doan Minh Tri Le Thi Huong Nguyen Manh Cuong Nguyen Huu Nghi Do Duc Bao Ninh Phong Le Thi Phuong Thao Nguyen Khac Vu Tran Van Chinh Luu Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles Journal of Chemistry |
| title | Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles |
| title_full | Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles |
| title_fullStr | Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles |
| title_full_unstemmed | Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles |
| title_short | Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles |
| title_sort | design synthesis and biological activity evaluation of novel azt and adenosine derived 1 2 3 triazoles |
| url | http://dx.doi.org/10.1155/2023/1605316 |
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