SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY OF SOME NOVEL 1,5 BENZODIAZEPINE DERIVATIVES
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.
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