Novel 3,4-diazabenzotropone compounds (2,3-benzodiazepin-5-ones): synthesis, unique reactivity, and biological evaluation.
Novel 3,4-diazabenzotropone compounds (2,3-benzodiazepin-5-ones): synthesis, unique reactivity, and biological evaluation.
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新型 3,4-二氮杂苯并环酮化合物（2,3-苯二氮卓-5-酮）：合成、独特的反应性和生物学评价。
作者：
Y. Matsuya;Hiroshi Katayanagi;Takuya Ohdaira;Zheng;T. Kondo;H. Nemoto*
利用官能化苯并环丁烯酮衍生物的4 π-8 π顺序电环化反应，首次实现了3，4-二氮杂苯并[B]托品酮的有效合成。这些化合物是高度缺电子的，并且在环境温度下容易形成胺加合物。此外，温和加热导致定量氮气挤出以产生茚酮衍生物。发现这些二氮杂苯并托品对人淋巴瘤细胞表现出有效的促凋亡活性。因此，新的胺催化的氮挤出反应和有趣的生物活性被发现是这些新的二氮杂苯并卓酮化合物的特征。
Efficient synthesis of 3,4-diazabenzo[b]tropone was first achieved utilizing 4pi-8pi sequential electrocyclic reactions of functionalized benzocyclobutenone derivatives. These compounds are highly electron deficient and readily form amine adducts at ambient temperature. Furthermore, gentle heating resulted in quantitative nitrogen extrusion to produce indenone derivatives. These diazabenzotropones were found to exhibit potent apoptosis-inducing activity against human lymphoma cells. Thus, novel amine-catalyzed nitrogen extrusion reactions and interesting bioactivities were found to be characteristic of these novel diazabenzotropone compounds.