New pyrimidine-benzoxazole/benzimidazole hybrids: Synthesis,antioxidant, cytotoxic activity,in vitro cyclooxygenase and phospholipase A2-V inhibition |
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| Institution: | 1. Pharmaceutical Chemistry Department, College of Pharmacy, Jouf University, Aljouf 2014, Saudi Arabia;2. Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt;3. School of Pharmaceutical Sciences, University Sains Malaysia, 11800 Pulau Pinang, Malaysia;1. Department of Pharmaceutical Chemistry, Delhi Institute of Pharmaceutical Sciences and Research (DIPSAR), Mehrauli-Badarpur Road, PushpVihar, Sector-3, New Delhi 110017, India;2. Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak 124001, India;1. School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Rd., Shanghai 200240, China;2. Department of Chemistry, University of Florida, Gainesville, FL, 32611-7200, USA;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University), New Delhi 110062, India;2. College of Pharmacy and Dentistry, Buraydah Private Colleges, Al-Qassim 31717, Saudi Arabia;3. School of Computational & Integrative Sciences, Jawaharlal Nehru University, New Delhi 110067, India;4. Department of Medicinal Chemistry, Maharishi Arvind College of Pharmacy Jaipur, Rajasthan 301 039, India;5. College of Clinical Pharmacy, University of Dammam, Dammam 31441, Saudi Arabia;6. Department of Pharmaceutical Sciences & Technology, Birla Institute of Technology, Mesra, Ranchi, Jharkhand 835 215, India;7. Department of Toxicology, Faculty of Science, Jamia Hamdard (Hamdard University), New Delhi 110062, India;1. Department of Chemistry, Sri Venkateswara University, Tirupati 517 502, Andhra Pradesh, India;2. Department of Molecular Reproduction Development and Genetics, Indian Institute of Science, Bangalore 560 012, Karnataka, India |
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| Abstract: | To enhance the cytotoxicity of benzimidazole and/or benzoxazole core, the benzimidazole/benzoxazole azo-pyrimidine were synthesized through diazo-coupling of 3-aminophenybenzimidazole (6a) or 3-aminophenylbenzoxazole (6b) with diethyl malonate. The new azo-molanates 6a&b mixed with urea in sodium ethoxide to afford the benzimidazolo/benzoxazolopyrimidine 7a&b. The structure elucidation of new synthesized targets was proved using spectroscopic techniques NMR, IR and elemental analysis. The cytoxicity screening had been carried out against five cancer cell lines: prostate cancer (PC-3), lung cancer (A-549), breast cancer (MCF-7), pancreas cancer (PaCa-2) and colon cancer (HT-29). Furthermore, the antioxidant activity, phospholipase A2-V and cyclooxygenases inhibitory activities of the target compounds 7a&b were evaluated and the new compounds showed potent activity (cytotoxicity IC50 range from 4.3 to 9.2 µm, antioxidant activity from 40% to 80%, COXs or LOX inhibitory activity from 1.92 µM to 8.21 µM). The docking of 7a&b was made to confirm the mechanism of action. |
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| Keywords: | Benzoxazole Benzimidazole Cytotoxicity COXs Antioxidant |
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