Design, synthesis, antimicrobial, anti-inflammatory, and analgesic activity of novel dihydrobenzo furo[3,2-e]isoxazolo[4,5-b]azepin-5(5aH)-ones

Novel series of dihydro benzofuro[3,2- e ]isoxazolo[4,5- b ]azepin-5(5 aH )-ones 6 have been synthesized from 3,5-dimethyl-4-nitroisoxazole 1 . Compound 1 on treatment with salicyl aldehydes afforded the corresponding nitrostyrylisoxazoles 3 , which upon reaction with ethyl bromo acetate followed by...

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Bibliographic Details
Published in:Medicinal chemistry research 2013-12, Vol.22 (12), p.6143-6153
Main Authors: Rajanarendar, E., Govardhan Reddy, K., Rama Krishna, S., Shireesha, B., Reddy, Y. N., Rajam, M. V.
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Original Research
Pharmacology/Toxicology
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Summary:Novel series of dihydro benzofuro[3,2- e ]isoxazolo[4,5- b ]azepin-5(5 aH )-ones 6 have been synthesized from 3,5-dimethyl-4-nitroisoxazole 1 . Compound 1 on treatment with salicyl aldehydes afforded the corresponding nitrostyrylisoxazoles 3 , which upon reaction with ethyl bromo acetate followed by cyclization with triethylamine furnished ethyl 2,3-dihydro-3-[(3-methyl-4-nitro-5-isoxazolyl)methyl]benzofuran-2-carboxylates 5 . Reductive cyclization of compounds 5 was effected with SnCl 2 –MeOH to give the title compounds 6 . Compounds 4 – 6 were characterized by IR, 1 H NMR, 13 C NMR and Mass spectral data. The title compounds 6a – g were evaluated for their antimicrobial, anti-inflammatory, LOX-5 inhibitory, and analgesic activity. Compounds 6b and 6c exhibited significant antimicrobial activity, potent anti-inflammatory and analgesic activities as that of standard drugs.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-013-0598-0