Abstract
3-Acetyl coumarins (1) when allowed react with isatin (2) gave corresponding 3-(3′-hydroxy-2′-oxo indolo) acetyl coumarins (3), which on dehydration afforded the correspondingα,β-unsaturated ketones (4). Cyclocondensation of (4) with substitutedo-phenylene diamines resulted in novel 3-coumarinyl spiro[indolo-1,5-benzodiazepines] (5). Structures of all the compounds have been established on the basis of their IR, NMR and mass spectral data and have been screened for their antimicrobial activity and antianxiety activity in mice
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References
Richer A G and Sternbach L H 1968Chem. Rev. 68 747
Smith R H, Jorgen W L, Tirado R J and Lamb M L 1998J. Med. Chem. 41 5272
Jadhav K P and Ingled D B 1983Indian J. Chem. B22 180
Reddy R J, Ashok D and Sharma P N 1993Indian J. Chem. B32 404
Satyanarayan K and Rao M N 1993Indian J. Pharm. Sci. 55 230
Dessarro G, Chimirri A, Dessaro A and Gitto R 1995Eur. J. Med. Chem. 30 925
Ishikawa SJpn. Kokai Tokkyo Koho Jp. 61 96, 650;Chem. Abstr. 106 11222g
Yoshihana I, Okuhara M and Yamamoto TEuri. Pat. Appl EP. 435 262;Chem. Abstr. 117 58904y
Knoevenagel E 1898Berichte 31 730
Bagchi P P and Ittyeah PI 1955Agra Univ. J. Res. 14 5
Kovonagh F 1963Analytical microbiology (New York: Academic Press) p. 125
Crawley J N and Godwin F K 1980 Preliminary of simple animal behavior model for effect of benzodiazepines.Pharm. Biochem. Behav. 167–170
Kilfoil T, Michel A and Montgomony D 1988Psycho. Pharmacol. 28 901
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Kusanur, R.A., Ghate, M. & Kulkarni, M.V. Synthesis of spiro[indolo-1,5-benzodiazepines] from 3-acetyl coumarins for use as possible antianxiety agents. J Chem Sci 116, 265–270 (2004). https://doi.org/10.1007/BF02708277
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DOI: https://doi.org/10.1007/BF02708277