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A facile one step synthesis of N-2 substituted 3-phenyliminoisoindolinones from N-(2-carboxybenzoyl)-anthranilic acid and the design of reverse-turn mimetics

Koley, P., Dutta, A., Drew, M. G. B., Kar, S. and Pramanik, A. (2009) A facile one step synthesis of N-2 substituted 3-phenyliminoisoindolinones from N-(2-carboxybenzoyl)-anthranilic acid and the design of reverse-turn mimetics. Arkivoc. pp. 12-24. ISSN 1424-6376

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Official URL: http://www.arkat-usa.org/arkivoc-journal/browse-ar...

Abstract/Summary

Stirring of N-(2-carboxybenzoyl) anthranilic acid with anilines and amines such as p-toluidine, benzylamine, methyl esters of Leu, Phe, Ile and Val in presence of DCC produces N- 2 substituted 3-phenyliminoisoindolinones in very good yields. Single crystal X-ray diffraction studies and solution phase NMR and CD studies reveal that the 3-phenyliminoisoindolinone moiety is a turn-inducing scaffold which should be useful for reverse-turn mimetics.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11399
Uncontrolled Keywords:N-(2-Carboxybenzoyl)anthranilic acid, 3-phenyliminoisoindolinones, amino acids, DCC mediated coupling, reverse-turn mimetics, CONFORMATIONAL-ANALYSIS, AMINO-ACIDS, DIPEPTIDE MIMICS, BICYCLIC, LACTAMS, MODEL PEPTIDES, PROTEINS, PEPTIDOMIMETICS, SCAFFOLDS, PRODUCTS, CRYSTAL

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