Abhishek Kumar, K. Ishwarbhat
Jul 1, 2016
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Influential Citations
8
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Quality indicators
Journal
Asian Journal of Pharmaceutical and Clinical Research
Abstract
ABSTRACT Objective: The objective of the study is to synthesize some novel 1,5-benzodiazepine derivatives from chalcones. The structures of the newly synthesized compounds were characterized by elemental analysis, infrared, H nuclear magnetic resonance, and mass spectroscopic studies. All titled compounds were screened for their anti-inflammatory activity. 1 Methods: In this study, a series of novel 2-(substituted phenyl)-3-styryl-2,3-dihydro-1H-benzo [b] [1,4] diazepine (1-12) has been synthesized from 1,5-(disubstituted phenyl)-2,4-pentadien-1-one (1a-12a). 1,5-(disubstituted phenyl)-2,4-pentadien-1-one was prepared by condensing cinnamaldehyde with various aromatic ketones in the presence of 20% NaOH as base. Different 1,5-(disubstituted phenyl)-2,4-pentadien-1-one on cyclisation with o-phenylene diamine in the presence of NaOH as base resulted in 2-(substituted phenyl)-3-styryl-2,3-dihydro-1H-benzo [b] [1,4] diazepine derivatives. The final synthesized benzodiazepine derivatives were screened for their anti-inflammatory activity using carrageenaninduced rat paw edema method. Results: The compounds 4, 5, 7, 9, 10, 11, and 12 containing 4-nitrophenyl, 4-chlorophenyl, 3-nitro phenyl, 4-fluorophenyl, 4-bromophenyl, and 3-chlorophenyl benzodiazepine derivatives exhibited significant anti-inflammatory activity compared with the standard diclofenac sodium The presence of electron withdrawing groups such as nitro, chloro, fluoro, and bromo resulted in increased anti-inflammatory activity. Conclusion: This study reports the successful synthesis of 1,5-benzodiazepine derivatives with moderate yields and most of the synthesized compounds showed significant anti-inflammatory activity. Keywords: Chalcones, 1,5-benzodiazepines, Anti-inflammatory activity.