Dawson M I, Chan R, Hobbs P D, Chao W R, Schiff L J
J Med Chem. 1983 Sep;26(9):1282-93. doi: 10.1021/jm00363a013.
Aromatic analogues of (E)-1-(4-carboxyphenyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)butadiene (1b) and its ethyl ester (1a) were synthesized as potential chemopreventive agents for the treatment of epithelial cancer and such skin diseases as psoriasis and cystic acne. The phenyl ring of 1 was replaced by 2-fluorophenyl, 2-methoxyphenyl, thienyl, furanyl, and pyridyl groups. The 1-fluorobutadiene analogue of 1 was also synthesized. With exception for the furanyl analogue, these compounds demonstrated good activity in reversing keratinization in hamster tracheal organ culture and in inhibiting the induction of ornithine decarboxylase in mouse epidermis by a tumor promoter.
合成了（E）-1-（4-羧基苯基）-2-甲基-4-（2,6,6-三甲基-1-环己烯-1-基）丁二烯（1b）及其乙酯（1a）的芳香类似物，作为治疗上皮癌以及银屑病和囊性痤疮等皮肤病的潜在化学预防剂。将1的苯环替换为2-氟苯基、2-甲氧基苯基、噻吩基、呋喃基和吡啶基。还合成了1的1-氟丁二烯类似物。除呋喃基类似物外，这些化合物在逆转仓鼠气管器官培养中的角质化以及抑制肿瘤启动子诱导小鼠表皮中的鸟氨酸脱羧酶方面表现出良好的活性。
