Click chemistry based multicomponent approach in the synthesis of spirochromenocarbazole tethered 1,2,3-triazoles as potential anticancer agents |
| |
| Institution: | 1. Department of Chemistry, Shivaji University, Kolhapur 416 004, India;2. Polymer Science and Engineering Division, CSIR, National Chemical Laboratory, Pune 411 008, India;3. Biochemistry Division, Department of Chemistry, Savitribai Phule Pune University, Pune 411007, India;4. Combi – Chem. Bio-Resource Centre, CSIR National Chemical Laboratory, Pune 411 008, India;1. Department of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah, 30002, Saudi Arabia;2. Department of Chemistry, Faculty of Science, University of Science and Technology Mohamed Boudiaf, Laboratoire de Chimie et Electrochimie des Complexes Metalliques (LCECM) USTO-MB, P.O. Box 1505, El M‘nouar, Oran, 31000, Algeria;3. Department of Chemistry, Jamia Millia Islamia (A Central University), New Delhi, 110025, India;1. Key Laboratory of Hubei Province for Coal Conversion and New Carbon Materials, Wuhan University of Science and Technology, Hubei, PR China;2. Pony Testing International Group (Wuhan), Hubei, PR China;3. Beijing University of Technology, Beijing, PR China;1. Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570006, India;2. Department of Studies in Molecular Biology, University of Mysore, Manasagangotri, Mysuru 570006, India;3. Cancer Science Institute of Singapore, National University of Singapore, Singapore 117599, Singapore;4. Adichunchanagiri Institute for Molecular Medicine (AIMM), BG Nagara, Nagamangala Taluk, Mandya district 571448, India;5. Laboratory of Chemical Biology, Department of studies in Organic Chemistry, University of Mysore, Manasagangotri, Mysuru 570006, India;6. Tsinghua-Berkeley Shenzhen Institute, Tsinghua University, Shenzhen, Guangdong 518005, PR China;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. Department of Physics, Thanthai Periyar Government Institute of Technology, Vellore, 632002, Tamil Nadu, India;2. Department of Physics, Thanthai Periyar EVR Government Polytechnic College, Vellore, 632002, Tamil Nadu, India;3. Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, 625021, Tamil Nadu, India;1. Institute of Natural Medicine & Green Chemistry, School of Chemical Engineering and Light Industry, Guandong University of Technology, Guangzhou 510006, China;2. School of Pharmaceutical Sciences, Tsinghua University, Beijing 100084, China;3. Universite Paris Diderot, Sorbonne Paris Cite, ITODYS, UMR 7086 CNRS, 15 rue J-A de Baif, 75270 Cedex 13 Pairs, France;4. Wuyi University, Jiangmen 529020, China;5. CNRS, UMR8601, Laboratoire de Chimine et Biochimie Pharmacologiques et Toxicologiques, CBNIT, Universite Paris Descartes PRES Sorbonne Paris Cite, UFR Bio5medicale, 45 rue des Saints-Peres, 75270 Paris Cedex 06, France |
| |
| Abstract: | A series of spirochromenocarbazole tethered 1,2,3-triazoles were synthesized via click chemistry based one-pot, five component reaction between N-propargyl isatins, malononitrile, 4-hydroxycarbazole, aralkyl halides and sodium azide using cellulose supported CuI nanoparticles (Cell-CuI NPs) as the heterogeneous catalyst. Antiproliferative activity of all the synthesized compounds was investigated against panel of cancer cell lines such as MCF-7, MDA-MB-231, HeLa, PANC-1, A-549, and THP-1. Many of the synthesized compounds exhibited good anti-proliferative activity against breast (MCF-7 and MDA-MB-231) and cervical (HeLa) cancer cells with IC50 values less than 10 μM. In case of MCF-7 cells, among the nine compounds that showed good anti-proliferative activity, compounds 6f and 6j were found to be highly potent (IC50 = 2.13 μM and 4.80 μM, respectively). In case of MDA-MB-231, three compounds (6k, 6j and 6s) showed antiproliferative activity amongst which 6k was the most potent one (IC50 = 3.78 μM). On the other hand, in cervical cancer HeLa cells, compounds 6b, 6g, 6s and 6u showed excellent antiproliferative activity (IC50 = 4.05, 3.54, 3.83, 3.35 μM, respectively). All the compounds were found to be nontoxic to the human umbilical vein endothelial cells (HUVECs). AO and EtBr staining and fluorescence microscopy studies of the active compounds (IC50 < 5 μM) suggested that these compounds induce cell death by apoptosis. |
| |
| Keywords: | Click chemistry 1 2 3-Triazolylspirochromenocarbazole Anticancer Cytotoxicity Apoptotic assay Heterogeneous catalysis Multicomponent synthesis |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
