1961 年 81 巻 1 号 p. 1-7
In order to test the bacteriostatic activity, some compounds related to 4H-1-benzothiopyran-4-one 1, 1-dioxide, a kind of isoster of 1, 4-naphthoquinone, were prepared as illustrated in Chart 1. Contrary to expectations, none of these compounds showed strong activity in vitro against Mycobac. tuberculosis and E. coli. It is supposed that the redox potential of quinones plays an important rôle in their bacteriostatic activity.
The half-wave potentials of some typical derivatives were measured by polarography. It was clarified that these compounds, which possessed 3-oxopropenylsulfonyl (-CO-CH=CH-SO2-) structure, showed comparatively positive reduction potential. This result agreed with the fact that 2-(phenylthio)thiochroman-4-one 1, 1-dioxide was easily produced from 3-bromo-4H-1-benzothiopyran-4-one 1, 1-dioxide and thiophenol in alkaline medium.