Synthesis, characterization of indomethacin derivatives bearing (۱,۳-oxazepine) ring and study of their biological activity

This study commenced with the synthesis of ethyl ۲-(۱-(۴-chlorobenzoyl)-۵-methoxy-۲-methyl-۱H-indol-۳-yl)acetate (۱) through the reaction of indomethacin with thionyl chloride in the presence of dimethylformamide (DMF). Subsequently, ۲-(۱-(۴-chlorobenzoyl)-۵-methoxy-۲-methyl-۱H-indol-۳-yl)acetohydrazide (۲) was produced by reacting the ester derivative (۱) with ۹۹% hydrazine hydrate in absolute ethanol. The reaction of hydrazide derivative (۲) with a variety of aromatic aldehydes in absolute ethanol, using glacial acetic acid as a catalyst, resulted in the synthesis of Schiff''s bases derivatives (۳, ۴). The cyclization of a prepared Schiff''s base (۳,۴) with a certain acid anhydride, such as maleic anhydride or ۳-nitrophthalic anhydride, in dry benzene is one method for synthesising the seven-membered rings (۱,۳-oxazepine derivatives) (۵-۸). The compounds that were produced (۱-۸) were studied using FT-IR and ۱H-NMR spectroscopy. In terms of antimicrobial activity in living organisms, the following bacteria exhibit high levels of activity: S. aureus (۸, ۳, and ۶), S. pneumonia (۸, ۳, and ۵), B. subtitilis (۸, ۳, and ۶), E. coli (۸, ۳, and ۶), P. aeruginosa (۸, ۶, and ۷), and K. pneumonia (۸, ۶, and ۳). The other bacteria exhibit moderate to low levels of activity. When tested against fluconazole, an antifungal medicine, Eight of the final compounds exhibited antifungal efficacy against Candida albicans, whereas the rest compounds shown limited action. The chemicals were made well, and tests of their antibacterial effectiveness reveal that they work like drugs.

کلیدواژه ها:

indomethacin ، Oxazepine ، Antimicrobial ، FT-IR ، H۱NMR spectroscopy