SYNTHESIS, ISOMER IDENTIFICATION BY 2D-NMR AND ANTIINFLAMMATORY EVALUATION OF SOME 9H-IMIDAZOLO[1,2-A]BENZIMIDAZOLE AND PERHYDRO IMIDAZOLO[1,2-D][1,2,4]DITHIAZEPINE DERIVATIVES
Sm. Sondhi et al., SYNTHESIS, ISOMER IDENTIFICATION BY 2D-NMR AND ANTIINFLAMMATORY EVALUATION OF SOME 9H-IMIDAZOLO[1,2-A]BENZIMIDAZOLE AND PERHYDRO IMIDAZOLO[1,2-D][1,2,4]DITHIAZEPINE DERIVATIVES, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 33(12), 1994, pp. 1144-1149
3-Phenyl-9H-imidazolo[1,2-a]benzimidazole derivatives (2a-c) and perhy
dro 4,4-tetramethylimidazolo[1,2-d][1,2,4]dithiazepine (6) on condensa
tion with methyl 2-bromo- and ethyl 2 bromopropanoate/ethanoate give t
he corresponding esters 3AB and 7. In case of 3AB6 both the isomers, i
.e. 3A6 and 3B6 have been separated by repeated column chromatography.
The structures of 3A6 and 3B6 have been assigned on the basis of H-1
and C-13 NMR spectral data and C-13-APT (C-13-attached proton test), H
MQC (proton-detected multiple quantum coherence), TOCSY (total coheren
ce spectroscopy) and HMBC (proton-detected multiple bond coherence) ex
periments. Condensation of o-phenylenediamine and 2,2'-dithiobis(2-met
hyl-propanal) gives 8. Anti-inflammatory evaluation of 2a-c, 3AB1-3AB1
2, 6, 7a-d and 8 has been carried out and some of the compounds such a
s 3AB1,3,4,10, 6 and 7a show 32, 34, 10, 17, 39 and 20.5% activity at
100 mg/kg p.o., respectively.