PREPARATION AND ANTIBACTERIAL ACTIVITIES OF NEW 1,2,3-DIAZABORINE DERIVATIVES AND ANALOGS
PREPARATION AND ANTIBACTERIAL ACTIVITIES OF NEW 1,2,3-DIAZABORINE DERIVATIVES AND ANALOGS
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DOI：
10.1021/jm00374a003
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发表时间：
1984-01-01
影响因子：
7.3
通讯作者：
HILDEBRANDT, J
中科院分区：
文献类型：
--
作者：
GRASSBERGER, MA;TURNOWSKY, F;HILDEBRANDT, J
在FeCl 3存在下，由芳烃醛或酮的（有机磺酰基）腙与三溴硼烷反应，合成了1，2-二氢-1-羟基-2-（有机磺酰基）芳烃[d][1，2，3]二氮杂硼杂环戊二烯2（芳烃=苯、萘、噻吩、呋喃、吡咯）。测定了化合物2的体外和体内抗菌活性，并对构效关系进行了讨论。本研究包括2，3-二氢-1-羟基-2-（对甲苯磺酰基）-1H-2，1-苯并氮杂硼杂环戊烯和1-羟基-1，2，3，4-四氢-2-（对甲苯磺酰基）-2，1-苯并氮杂硼杂环戊烯，以及碳环苯并二氮杂硼杂环戊烯类似物4-羟基-3-（对甲苯磺酰基）异喹啉。活性物种的性质进行了简要讨论。
1,2-Dihydro-1-hydroxy-2-(organosulfonyl)areno[d][1,2,3]diazaborines 2 (arene = benzene, naphthalene, thiophene, furan, pyrrole) were synthesized by reaction of (organosulfonyl)hydrazones of arene aldehydes or ketones with tribromoborane in the presence of FeCl3. The activities of 2 against bacteria in vitro and in vivo (Escherichia coli) were determined and structure-activity relationships are discussed. Included in this study are 2,3-dihydro-1-hydroxy-2-(p-tolylsulfonyl)-1H-2,1-benzazaborole and 1-hydroxy-1,2,3,4-tetrahydro-2-(p-tolylsulfonyl)-2,1-benzazaborine, as well as the carbacyclic benzodiazaborine analog 4-hydroxy-3-(p-tolylsulfonyl)isoquinoline. The nature of the active species is briefly discussed.