p-Quinone methides as geometric analogues of quinolone carboxylate antibacterials

Abstract

In an attempt to examine the role of the N(I)-alkyl or -aryl moiety of the quinolone antibacterials, several quinone methides such as perinaphthindenone carboxylates (6) were synthesized as 1-carba(sp(2)) analogues of the quinolone structure, and found to have no antibacterial activity. These results together with literature information are interpreted as the necessity of a: least one nitrogen atom at the position of 1, 3, 4a, 6 or 8 in the quinolone-like skeleton for the antibacterial activities. Copyright (C) 1996 Elsevier Science Ltd