Synthesis and Antiinflammatory Activity of New N‐Acyl‐5‐bromoanthranilamides.

Abstract

2005 Carboxylic amides Q 0490Synthesis and Antiinflammatory Activity of New N-Acyl-5-bromoanthranilamides. -(DOLZHENKO-PODCHEZERTSEVA, A. V.; KORKODINOVA, L. M.; VIZGUNOVA, O. L.; KOTEGOV, V. P.; VASILYUK, M. V.; Khim.-Farm. Zh. 38 (2004) 8, 27-28; Permskaya gos. farm. akad., Perm' 614600, Russia; Russ.) -Mischke 03-097

Synthesis and biological activity of N-acyl-5-bromanthranilic acids

“…It should be recalled that previously we demonstrated [8,9] that N-acyl-5-bromanthranilic acid amides inhibit the carrageenan edema model development more effectively than the corresponding acids, in agreement with the established general rule [17]. The inverse trend is observed with respect to the antimicrobial action [10,17].…”

“…A series of N-acyl derivatives (II -X) were obtained via the interaction of 5-bromanthranilic acid with the corresponding acid chloroanhydrides in benzene. The reactions were carried out with heating on a water bath for 30 -40 min [8].…”

Synthesis, antiproliferative activity, and mechanism of action of a series of 2-{[(2E)-3-phenylprop-2-enoyl]amino}benzamides

“…The anthranilamide derivatives 10b,c were obtained by stirring the appropriate 2 H -3,1-benzoxazine-2,4(1 H )-dione 9b,c in aqueous ammonia solution (Scheme 1) [8]. …”

“…The reaction gave a mixture of ( E )-6-iodo-2-styryl-4H-benzo[d] [1,3]oxazin-4-ones 14t – u and 2-cinnamamido-5-iodobenzoic acids 15t – u , and the mixtures were treated with aqueous Na 3 PO 4 [9] to give the corresponding acids 15t [10], 15u,v as the only products. By treating the acids 15t – v with ethyl chloroformate, the 2 H -3,1-benzoxazine-2,4-diones 16t – v were obtained [11], which, in turn, converted to the 2-{[2 E ]-3-phenyl-prop-2-enoylamino}benzamides 17t – v by refluxing them in an aqueous ammonia solution [8]. …”

Synthesis and the Antiinflammatory Activity of New N-Acyl-5-Bromanthranilamides

“…This anhydride was preliminarily synthesized through oxidation of 5-bromisatin by chromium(VI) oxide [7]. N-acyl derivatives (II -XX) were obtained using the procedures described previously [8,9].…”