V. O. Koz’minykh, A. O. Belyaev, E. N. Koz’minykh
Nov 1, 2004
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Journal
Pharmaceutical Chemistry Journal
Abstract
As is known, aroylpyruvic acids (I) attach amines under mild conditions at the carbonyl group in position C with the formation of N-substituted 2-amino-4-aryl-4-oxo-2-butenoic acids [1 – 8]. Previously, it was reported that 2-cyclohexylamino, some 2-arylamino-, 2-morpholyl-, and 2-heterylamino-4-aryl-4-oxo-2-butenoic acids exhibit moderate antimicrobial and analgesic activity [6 – 8]. In continuation of the search for biologically active substances among substituted 2-amino-4-aryl-4-oxo-2-butenoic acids, we have synthesized a series of 4-aryl-2-tert-butylamino-4-oxo-2-butenoic acids (IIa – IIg) via interaction of aroylpyruvic acids (Ia – Ig) with tert-butylamine [9 – 11]. Compounds IIa – IIg appear as colorless crystalline substances, which are soluble in DMSO, sparingly soluble in ethanol and benzene, and insoluble in water.