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Chapter 6
Synthesis of benzodiazepines
6.2 Biological activities associated with diazepine derivatives
Buckle et al. 42 has prepared 1H-benzo-1,5-diazepine-2,4-(3H,5H)-diones
(Figure-2) from 4,2-R 2 (NH 2 )C 6 H 3 NH 2 (R 2 = H, Cl, F, COOH) by refluxing with
malonic acid in 4N HCl for half an hour followed by nitration with fuming HNO 3
which is antiallergic substance useful in the treatment of rhinitis, hay fever and certain
type of asthma.
Figure-2
K. S. Andronati et al. 43 has prepared 3-Amino-1,2-dihydro-3h-1,4-
benzodiazepin-2-one derivatives (Figure-3) via interaction with 3-chloro
benzodiazepines, diethylamine, 1,6-diaminohexane, or p-nitroaniline, which is exhibit
a pronounced anticonvulsant activity and produce significant anorexigenic effect.
H
N
O
Br
N
R 2
R 1
R 1 =H,Cl
R 2 =N(C 2 H 5 ) 2 , NH(CH 2 ) 6 NH 2
Figure-3
More recent analogues of the Benzodiazepines have attracted interest as anti
HIV compounds, such as the clinically used nevirapine and as anticancer compounds,
such as the pyrrolo fused antitumor antibiotic DC-18 (Figure-4), analogues of which
are in clinical development as anticancer agents. 44
Figure-4
Department of Chemistry, Saurashtra University, Rajkot-360005 203