Novel 3,4-diazabenzotropone compounds (2,3-benzodiazepin-5-ones): synthesis, unique reactivity, and biological evaluation.
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.
Matsuya
Yuji
Y
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan. matsuya@pha.u-toyama.ac.jp
Katayanagi
Hiroshi
H
Ohdaira
Takuya
T
Wei
Zheng-Li
ZL
Kondo
Takashi
T
Nemoto
Hideo
H
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D014334:Tropolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000970:Antineoplastic Agents; D001569:Benzodiazepines; D014334:Tropolone; C003730:tropone