Click chemistry-assisted synthesis of novel aminonaphthoquinone-1,2,3-triazole hybrids and investigation of their cytotoxicity and cancer cell cycle alterations |
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| Affiliation: | 1. Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran;2. Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran;3. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran;1. Universidade Federal Fluminense, Departamento de Química Orgânica, Instituto de Química, Campus do Valonguinho, Niterói, RJ, CEP 24020-150, Brazil;2. Universidade Federal do Rio de Janeiro, Laboratório de Tecnologia Industrial Farmacêutica (LabTIF), Faculdade de Farmácia, Rio de Janeiro, RJ, CEP 21941-902, Brazil;3. Universidade Federal do Rio de Janeiro, Laboratório de Modelagem Molecular e Pesquisa em Ciências Farmacêuticas (LaMCiFar), NUPEM, Campus Macaé, RJ, CEP 27965-045, Brazil;4. Universidade Federal Fluminense, Departamento de Tecnologia Farmacêutica, Faculdade de Farmácia, Niterói, RJ, CEP 24241-002, Brazil;1. State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Haihe Education Park, 38 Tongyan Road, Tianjin, 300353, People''s Republic of China;2. Accendatech Company, Ltd., Tianjin, 300384, People''s Republic of China;1. Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Av. Antônio Carlos, 6627, Campus Pampulha, CEP 31270-901 Belo Horizonte, MG, Brazil;2. Faculdade de Farmácia, UFOP, Rua Costa Sena 171, CEP 35400-000 Ouro Preto, MG, Brazil;3. Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Antônio Carlos, 6627, Campus Pampulha, CEP 31270-901 Belo Horizonte, MG, Brazil;4. Programa de Pós-Graduação em Bioinformática, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Av. Antônio Carlos, 6627, Campus Pampulha, CEP 31270-901 Belo Horizonte, MG, Brazil;1. Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Viet Nam;2. Lab of Profession Chemistry, Institute of Biochemical Technology and Profession Documents, General Department 4 (Ministry of Public Security), 80 Tran Quoc Hoan, Cau Giay, Ha Noi, Viet Nam;3. Institute for Chemistry and Materials, Military Institute of Science and Technology, 17 Hoang Sam, Cau Giay, Ha Noi, Viet Nam;4. Viet Tri University of Industry, Tien Kien, Lam Thao, Phu Tho, Viet Nam;5. Thai Nguyen College of Education, Quang Trung, Thinh Dan, Thai Nguyen, Viet Nam;6. Faculty of Chemistry, Thai Nguyen University of Education, 20 Luong Ngoc Quyen, Thai Nguyen, Viet Nam;1. Academy of Scientific and Innovative Research (AcSIR), CSIR-IIIM, Jammu Campus, Jammu 180001, India;2. Bio-organic Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India;3. Department of Chemistry, National Institute of Technology (NIT), Jalandhar 144011, Punjab, India;1. College of Pharmaceutical Science, Collaborative Innovation Center of Yangtza River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, PR China;2. Shanghai Evergene Biotech Co,. Ltd., Shanghai 201499, PR China;3. College of Chemical Engineering and Materials Science, Tianjin University of Science & Technology, Tianjin 300457, PR China;4. Shanghai Institute for Advanced Immunochemical Studies, ShanghaiTech University, Shanghai 201210, PR China;5. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, PR China |
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| Abstract: | A series of 12 novel 1,4-naphthoquinone-1,2,3-triazole hybrids were designed and synthesized through copper-catalyzed click reaction of 2-(prop-2-ynylamino)naphthalene-1,4-dione (3) and different azidomethyl-benzene derivatives. The synthesized compounds were assessed for their anticancer activity against three cancer cell lines (MCF-7, HT-29 and MOLT-4) by MTT assay. The results showed that the majority of the synthesized compounds displayed cytotoxic activity. Derivatives 6f and 6h, bearing 4-trifluoromethyl-benzyl and 4-tert-butyl-benzyl groups, respectively, as well as intermediate 3 demonstrated good cytotoxic potential against all tested cancer cell lines, among which compound 6f showed the highest activity. Flow cytometric analysis revealed that compounds 3, 6f and 6h arrested cell cycle at G0/G1 phase in MCF-7 cells. Therefore, synthesized aminonaphthoquinone-1,2,3-triazole derivatives can be introduced as promising molecules for further development as potential anticancer agents. |
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| Keywords: | 1, 4-Naphthoquinone 1, 2, 3-Triazoles Click chemistry Anticancer effect Cancer cell |
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