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Chapter 6
Synthesis of benzodiazepines
Rubin et al. 45 have synthesized 4-phenyl-2-trichloromethyl-3H-1,5-
benzodiazepine hydrogen sulphate and examined its pharmacological effects in mice,
keeping diazepam as reference. The data suggest that this recently synthesized
compound possesses anxiolytic activity and produces motor in co-ordination similar
to those observed with diazepam.
The synthesis of a new class of annulated 1,4-benzodiazepines with antipsychotic
activity was exemplified by preparation of 10-fluoro-3-methy1-7-(2-
thieny1)-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,4]benzodiazepine(Figure-5). The
influence of variations of the fluoro-substitution pattern and variations of the fused
ring system on the biological activity of the structural analogues was evaluated. 46
Figure-5
3-Acetyl coumarins when allowed react with isatin gave corresponding 3-(3’-
hydroxy-2’-oxoindolo)acetylcoumarins, which on dehydration afforded the
corresponding α,β-unsaturated ketones. Which on cyclocondensation with substituted
o-phenylenediamines resulted in novel4-(2-oxo-2H-chromen-3-yl)-1,5-dihydrospiro
[benzo[b][1,4]diazepine-2,3'-indolin]-2'-one (Figure-6). All the compounds have
been screened for their antimicrobial and antianxiety activity in mice. 47
Figure-6
A library of compounds targeted to the vasopressin/oxytocin family of
receptors was screened for activity at a cloned human oxytocin receptor using a
reporter gene assay. Potency and selectivity were optimized to afford compound
(Figure-7), EC 50 =33 nM. This series of compounds represents the first disclosed,
non-peptide, low molecular weight agonists of the hormone oxytocin. 48
Department of Chemistry, Saurashtra University, Rajkot-360005 204