The antibacterial action of some stilbene derivatives

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Abstract
The wide distr. of cyclopentanophenanthrene derivatives in living matter suggested the use of this spatial framework to carry known antibacterial groups into contact with vital systems. The diethylstilbene molecule offers a similar space configuration with the intense physiol. activity unimpaired and capable of ready chemical synthesis. A series of stilbene derivatives containing known antibacterial groupings was prepd. and several are descr. with exceptional antibacterial properties against staphylococci and streptococci, the most active being 4- OH [center dot] CeH4 [center dot] CEt = CEt [center dot] CbH5, which is some 40 times as active as the mould metabolic product citrinin and as active as chloroxylenol under the conditions of the tests. The solubility of all the compounds is low, the most soluble being of the order of 0.1% in the medium. The antibacterial and estrogenic activities are not concurrent. In vivo the compounds tested show no activity. The following new compounds were prepd.:[long dash]C6H5 [center dot] C(OH)Et [center dot] CHEt.C6H6[long dash]b.p. 182-186[degree] at 14 mm.; 4-MeO [center dot] C8H4 [center dot] C6H4 [center dot] CHEt [center dot] CHEt [center dot] C6H6[long dash]m.p. 89-90[degree]; 4-OH [center dot] CeH4 [center dot] CHEt [center dot] CHEt [center dot] CH5[long dash]m.p. 139-140[degree] (benzoate m.p. 110[degree]) [center dot] Pyridine salt of 4-HSO3 [center dot] O [center dot] CeH4 [center dot] CHEt [center dot] CHEt [center dot] C6H5[long dash]m.p. 195-196[degree]; 4-OH [center dot] C6H4 [center dot] CEt = CEt [center dot] C6H4 [center dot] 0Me4''-m.p. 101-102[degree]; C6H5 [center dot] CO [center dot] CHEt [center dot] CeH4 [center dot] NH2-4[long dash]m.p. 128-129[degree]; C.H.. C(OH)Et- CHEt [center dot] C6H4 [center dot] NH2-4[long dash]m.p. 91-92[degree]; CaH5 [center dot] CEt = CEt [center dot] CeH4 [center dot] NH2-4[long dash]m.p. 96-97[degree] (Hydro-chloride 254-255 [degree]); C8H5 [center dot] CEt = CEt [center dot] C6H* [center dot] NH [center dot] S02 [center dot] CaH4[image]NH2-4[long dash]m.p. 180-182[degree] (N4-acetyl derivative m.p. 207-208[degree]); 4-OH [center dot] C6H4 [center dot] CH = CH [center dot] C6H4 [center dot] NH2-4[long dash]m.p. 270-271[degree]; 4-OH. C8H4-CH = CH [center dot] C.H [center dot] CN-4[image][long dash]m.p. 221-223[degree]; 4-OH [center dot] C6H4 [center dot] CH = CH [center dot] G,H4 [center dot] C [image] [center dot] HC1 [center dot] 4[long dash]m.p. 316-317[degree].

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