Microwave assisted synthesis of dihydrobenzo4,5imidazo1,2-apyrimidin-4- ones; {Synthesis}, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo4,5imidazo1,2-apyrimidin-4-ones

Puttaraju, K. B. and Shivashankar, K. and Chandra and Mahendra, M. and Rasal, V. P. and Venkata Vivek, P. N. and Khushboo Rai and Chanu, M. B. (2013) Microwave assisted synthesis of dihydrobenzo4,5imidazo1,2-apyrimidin-4- ones; {Synthesis}, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo4,5imidazo1,2-apyrimidin-4-ones. European Journal of Medicinal Chemistry, 69. pp. 316-322. ISSN 0223-5234

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Official URL: http://doi.org/10.1016/j.ejmech.2013.07.015

Abstract

The present article describes the synthesis of dihydrobenzo4,5imidazo1, 2-apyrimidin-4-one (2a-h) under microwave irradiation. The product was obtained in excellent yield (74-94\%) in a shorter reaction time (2 min). These molecules (2a, b) further reacted with various substituted 4-bromomethylcoumarins (3a-f) to yield a new series of coumarin substituted dihydrobenzo4,5imidazo1,2-a pyrimidin-4-ones (4a-h). The structure of all the synthesized compounds were confirmed by spectral studies and screened for their in vitro antibacterial activity against three Gram-positive bacteria viz., Staphylococcus aureus, Enterococcus faecalis, Streptococcus mutans and three Gram-negative bacteria viz., Escherichia coli, Klebsiella pneumonia, Pseudomonas aeruginosa and antifungal activity against Candida albicans, Aspergillus niger, Aspergillus fumigatus, Aspergillus flavus, Fusarium oxysporum, Penicilliumchrysogenum and anticancer activity against Dalton's Ascitic Lymphoma (DAL) cell line. In general, all the compounds possessed better antifungal properties than antibacterial properties. The coumarin substituted dihydrobenzo4,5imidazo1,2- apyrimidin-4-one (4g) (R = i-Pr, R1 = 6-Cl) was found to be the most potent cytotoxic compound (88\%) against Dalton's Ascitic Lymphoma cell line at the concentration of 100 μg/mL.

Item Type: Article
Uncontrolled Keywords: 10 (6, 10 (6 bromo 2 oxo 2h chromen 4 ylmethyl) 2 isopropyl 10h benzo4, 10 (6 chloro 2 oxo 2h chromen 4 ylmethyl) 2 isopropyl 10h benzo4, 10 (6 fluoro 2 oxo 2h chromen 4 ylmethyl) 2 isopropyl 10h benzo4, 10 (6 fluoro 2 oxo 2h chromen 4 ylmethyl) 2 trifluoromethyl 10h benzo4, 10 (6 methoxy 2 oxo 2h chromen 4 ylmethyl) 2 isopropyl 10h benzo4, 10 (6 methoxy 2 oxo 2h chromen 4 ylmethyl) 2 trifluoromethyl 10h benzo4, 10 (6 methyl 2 oxo 2h chromen 4 ylmethyl) 2 trifluoromethyl 10h benzo4, 2 (3 fluoro phenyl) 10H benzo4, 2 (4 trifluoromethyl phenyl) 10h benzo4, 2 apyrimidin 4 one, 2 isopropyl 10h benzo4, 4-Bromomethylcoumarins, 5imidazo1, 8 dimethyl 2 oxo 2h chromen 4 ylmethyl) 2 trifluoromethyl 10h benzo4, Anti-Bacterial Agents, antibacterial activity, antifungal activity, Antifungal Agents, antimicrobial activity, antineoplastic activity, Antineoplastic Agents, Antitumor, article, Aspergillus flavus, Aspergillus fumigatus, Aspergillus niger, Bacteria, Benzimidazole, Benzimidazoles, cancer cell culture, Candida albicans, Cell Line, Cell Proliferation, chemical structure, ciprofloxacin, coumarin derivative, Coumarins, Drug Screening Assays, drug structure, drug synthesis, Enterococcus faecalis, Escherichia coli, fluconazole, fluorouracil, Fungi, Fusarium oxysporum, Humans, in vitro study, Klebsiella pneumoniae, lymphoma cell line, Microbial Sensitivity Tests, microwave irradiation, Microwaves, minimum inhibitory concentration, Models, Molecular, Molecular Structure, nonhuman, Penicillium chrysogenum, Pseudomonas aeruginosa, Pyrimidine, pyrimidine derivative, Pyrimidinones, reaction time, Staphylococcus aureus, Streptococcus mutans, Tumor, unclassified drug
Subjects: D Physical Science > Physics
Divisions: Department of > Physics
Depositing User: Arshiya Kousar Library Assistant
Date Deposited: 23 Oct 2019 06:36
Last Modified: 12 Jan 2023 09:15
URI: http://eprints.uni-mysore.ac.in/id/eprint/9114

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