SYNTHESIS AND STRUCTURE ELUCIDATION OF 5-AMINOMETHINIMINO-3-METHYL-4-ISOXAZOLECARBOXYLIC ACID PHENYLAMIDES AND THEIR IMMUNOLOGICAL ACTIVITY

A series of 15-aminomethinimino-3-methyl-4-isoxazolecarboxylic acid ph enylamides 4 has been prepared by condensation of 5-amino-3-methyl-4-i soxazolecarboxylic acid phenylamides 1 with trichloroacetic aldehyde. Alcoholysis of trichloro derivatives 2 gave 5-alkoxymethine derivative s 3 which, on reaction with an appropriate amine, formed the correspon ding compounds 4. The compounds obtained were evaluated for their immu nological activity. The properties of three compounds, described in th is report, permitted inhibition of the immune response in all possible ways: diminishing both types of immune response (4d), humoral immune response (4a), or cellular immune response (4c). Preparation 4d is com parable in its effectiveness to CsA, so it may be potentially used as an agent for prolongation of the function of transplanted organs. Two other compounds may potentially be used in cases where only one type t he immune response is required for combating pathogen invasion.