Synthesis, anticancer and molecular docking studies of new class of benzoisoxazolyl-piperidinyl-1, 2, 3-triazoles
A small library of hitherto unexplored novel 5-fluorobenzoisoxazolyl-piperidinyl-1, 2, 3-triazole derivatives has been synthesized from 2-azido-fluorobenzoisoxazolyl piperidinyl ethanone and various alkynes in good to excellent yields through a click chemistry approach. Compounds thus synthesized we...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2020-12-01
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| Series: | Journal of King Saud University: Science |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1018364720302809 |
| _version_ | 1818163976179023872 |
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| author | Govindhan Muniyappan Subramanian Kathavarayan Chandrasekar Balachandran Easwaramoorthi Kalliyappan Sakkarapalayam M. Mahalingam Abdul Ajees Abdul Salam Shin Aoki Natarajan Arumugam Abdulrahman I. Almansour Raju Suresh Kumar |
| author_facet | Govindhan Muniyappan Subramanian Kathavarayan Chandrasekar Balachandran Easwaramoorthi Kalliyappan Sakkarapalayam M. Mahalingam Abdul Ajees Abdul Salam Shin Aoki Natarajan Arumugam Abdulrahman I. Almansour Raju Suresh Kumar |
| author_sort | Govindhan Muniyappan |
| collection | DOAJ |
| description | A small library of hitherto unexplored novel 5-fluorobenzoisoxazolyl-piperidinyl-1, 2, 3-triazole derivatives has been synthesized from 2-azido-fluorobenzoisoxazolyl piperidinyl ethanone and various alkynes in good to excellent yields through a click chemistry approach. Compounds thus synthesized were evaluated for their cytotoxicity against HepG-2 and A549 cancer cells. Interestingly, compounds 4c, 4d, 4e and 4h displayed significant cytotoxicity against HepG-2 and A549 cancer cells. Toxicity study of active compounds was compared with human normal lung IMR-90 cells. Molecular docking has also been investigated for 4a-i with Chk1 protein and the compounds 4c and 4h displayed reasonable molecular interactions with good docking scores. |
| first_indexed | 2024-12-11T16:58:07Z |
| format | Article |
| id | doaj.art-ae65e9ab47524d0fb61e15feef2fe346 |
| institution | Directory Open Access Journal |
| issn | 1018-3647 |
| language | English |
| last_indexed | 2024-12-11T16:58:07Z |
| publishDate | 2020-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of King Saud University: Science |
| spelling | doaj.art-ae65e9ab47524d0fb61e15feef2fe3462022-12-22T00:57:54ZengElsevierJournal of King Saud University: Science1018-36472020-12-0132832863292Synthesis, anticancer and molecular docking studies of new class of benzoisoxazolyl-piperidinyl-1, 2, 3-triazolesGovindhan Muniyappan0Subramanian Kathavarayan1Chandrasekar Balachandran2Easwaramoorthi Kalliyappan3Sakkarapalayam M. Mahalingam4Abdul Ajees Abdul Salam5Shin Aoki6Natarajan Arumugam7Abdulrahman I. Almansour8Raju Suresh Kumar9Department of Chemistry, Anna University, Chennai-600 020, Tamil Nadu, India; Drug Discovery Research, Orchid Chemicals & Pharmaceuticals Ltd., R&D Centre, Sholinganallur, Chennai-600 119, Tamil Nadu, IndiaDepartment of Chemistry, Anna University, Chennai-600 020, Tamil Nadu, IndiaFaculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda 278-8510 JapanR&D Centre, Malladi Drugs & Pharmaceuticals Ltd, Chennai-6000124, TN, IndiaDeparatment of Chemistry, SRM Institute of Science and Technology, Kattankulathur, Chengalpattu 603203, India; Corresponding authors.Department of Atomic and Molecular Physics, Centre for Applied Nanosciences, Manipal Academy of Higher Education, Manipal, 576104, Karnataka, IndiaFaculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda 278-8510 Japan; Research Institute for Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda 278-8510 JapanDepartment of Chemistry, College of Science, King Saud University, P.O.Box 2455, Riyadh 11451, Saudi Arabia; Corresponding authors.Department of Chemistry, College of Science, King Saud University, P.O.Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O.Box 2455, Riyadh 11451, Saudi ArabiaA small library of hitherto unexplored novel 5-fluorobenzoisoxazolyl-piperidinyl-1, 2, 3-triazole derivatives has been synthesized from 2-azido-fluorobenzoisoxazolyl piperidinyl ethanone and various alkynes in good to excellent yields through a click chemistry approach. Compounds thus synthesized were evaluated for their cytotoxicity against HepG-2 and A549 cancer cells. Interestingly, compounds 4c, 4d, 4e and 4h displayed significant cytotoxicity against HepG-2 and A549 cancer cells. Toxicity study of active compounds was compared with human normal lung IMR-90 cells. Molecular docking has also been investigated for 4a-i with Chk1 protein and the compounds 4c and 4h displayed reasonable molecular interactions with good docking scores.http://www.sciencedirect.com/science/article/pii/S10183647203028091,2,3-TriazolesClick chemistry reactionAnticancer activityMolecular docking studies |
| spellingShingle | Govindhan Muniyappan Subramanian Kathavarayan Chandrasekar Balachandran Easwaramoorthi Kalliyappan Sakkarapalayam M. Mahalingam Abdul Ajees Abdul Salam Shin Aoki Natarajan Arumugam Abdulrahman I. Almansour Raju Suresh Kumar Synthesis, anticancer and molecular docking studies of new class of benzoisoxazolyl-piperidinyl-1, 2, 3-triazoles Journal of King Saud University: Science 1,2,3-Triazoles Click chemistry reaction Anticancer activity Molecular docking studies |
| title | Synthesis, anticancer and molecular docking studies of new class of benzoisoxazolyl-piperidinyl-1, 2, 3-triazoles |
| title_full | Synthesis, anticancer and molecular docking studies of new class of benzoisoxazolyl-piperidinyl-1, 2, 3-triazoles |
| title_fullStr | Synthesis, anticancer and molecular docking studies of new class of benzoisoxazolyl-piperidinyl-1, 2, 3-triazoles |
| title_full_unstemmed | Synthesis, anticancer and molecular docking studies of new class of benzoisoxazolyl-piperidinyl-1, 2, 3-triazoles |
| title_short | Synthesis, anticancer and molecular docking studies of new class of benzoisoxazolyl-piperidinyl-1, 2, 3-triazoles |
| title_sort | synthesis anticancer and molecular docking studies of new class of benzoisoxazolyl piperidinyl 1 2 3 triazoles |
| topic | 1,2,3-Triazoles Click chemistry reaction Anticancer activity Molecular docking studies |
| url | http://www.sciencedirect.com/science/article/pii/S1018364720302809 |
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