SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF METHYL ESTERS OF 2-(HET)ARYLAMINO-4-OXO-Z-2-BUTENOIC ACIDS, THEIR STRUCTURAL ANALOGS, AND CONVERSION PRODUCTS

摘要

The beta-diketone moiety is an important structural feature in biologically active compounds. In particular, compounds containing a P-diketo acid and its biological isomers have recently been of great interest [1,2]. Keeping in mind tautom-erism, the aminovinylketone moiety can be viewed as a biological isomer of a p-diketone. Thus, amino and hydrazino derivatives of P-diketones may also be promising for studies of antimicrobial activity in particular [3,4]. We used known reactions [5, 6] to synthesize a small library of compounds with the aminovinylketone moiety in order to study the antimicrobial activity. These were (het)aroyl-pyrotartaric derivatives 2-(het)arylamino-4-oxo-Z-2-bute-noates (IIIa - n, t-v, and y-au) and their structural analogs 2-arylamino-l,4-diaryl-2-buten-l,4-diones (IIIo - s, w, and x). Methyl-3-(het)aroyl-l-aryl-2,4-dihydroxy-5-oxo-2,5-dihydro-l//-pyrrol-2-carboxylates V were prepared for 2-arylamino-4-oxo-Z-2-butenoates (Scheme).