Habib N S, Rieker A, Tawil G G
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, Egypt.
Farmaco. 1994 Jul-Aug;49(7-8):519-26.
Three novel series of 2,6-di-tert-butyl-1,4-benzoquinone derivatives were synthesized: 4-[(3,4-disubstituted-2,3-dihydrothiazol-2-ylidene) hydrazono]-2,6-di-tert-butyl-2,5-cyclohexadien-1-ones, 4-[(3-substituted-5-carbethoxy-4-methyl-2,3-dihydrothiazol-2- ylidene)hydrazono]-2,6-di-tert-butyl-2,5-cyclohexadien-1-one s, and 4-[(3-substituted-4-oxothiazolidin-2-ylidene)hydrazono]-2,6- di-tert- butyl-2,5-cyclohexadien-1-ones. These compounds were prepared by cyclization of the new 4-(N-substituted thiocarbamoylhydrazono)-2,6-di-tert-butyl-2,5-cyclohexadien- 1-ones with phenacyl bromides, ethyl alpha-chloroacetoacetate and ethyl bromoacetate, respectively. Antimicrobial testing of the prepared compounds and of the key intermediate thiosemicarbazones was performed. Some of the compounds revealed higher activity than streptomycin.
合成了三个新型系列的2,6-二叔丁基-1,4-苯醌衍生物：4-[(3,4-二取代-2,3-二氢噻唑-2-亚基)肼基]-2,6-二叔丁基-2,5-环己二烯-1-酮、4-[(3-取代-5-乙氧羰基-4-甲基-2,3-二氢噻唑-2-亚基)肼基]-2,6-二叔丁基-2,5-环己二烯-1-酮和4-[(3-取代-4-氧代噻唑烷-2-亚基)肼基]-2,6-二叔丁基-2,5-环己二烯-1-酮。这些化合物分别通过新的4-(N-取代硫代氨基甲酰肼基)-2,6-二叔丁基-2,5-环己二烯-1-酮与苯甲酰溴、α-氯代乙酰乙酸乙酯和溴乙酸乙酯环化制备。对所制备的化合物以及关键中间体硫代半卡巴腙进行了抗菌测试。其中一些化合物显示出比链霉素更高的活性。
