DR-4365
Chemical Name: N,N-Dimethyl-2-[4-[2-oxo-1,2,2a,3,4,5-hexahydrobenzo[cd]indol-2-yl]butyl]-2,3,4,9-tetrahydro-1H-beta-carboline-9-carboxamide
CAS No. 230300-64-8, 247082-25-3 ((S)-isomer)
项目整合开发状态: Preclinical
项目研究机构: Meiji Seika (Originator)
合成路线:Intermediate (III) is prepared by the following route.Acylation of 2-Boc-tetrahydropyridoindole (I) with dimethylcarbamoyl chloride provides the 9-carbamoyl derivative (II).Subsequent Boc group cleavage under acidic conditions furnishes amine (III).
合成路线:Tetrahydrobenzo[cd]indol-2-one (IV) is selectively alkylated at position 2a with 1,4-dibromobutane (V) in the presence of NaH to provide the bromobutyl derivative (VI).Then,condensation of bromide (VI) with amine (III) employing K2CO3 in DMF leads to the title compound.
📌 参考资料/链接：
参考文献标题:Tetrahydrobenzindole derivs.
文献作者:Koyama,M.; Okuno,M.; Hiranuma,T.; Ando,T.; Fuji,K.; Ushiroda,O.; Kikuchi,C.; Shiiyama,M.; Satoh,E.(Meiji Seika Kaisha,Ltd.)
参考来源:EP 1057814; JP 1999189585; US 6498251; WO 9933804
📄 详细内容
合成路线:Tetrahydrobenzo[cd]indol-2-one (IV) is selectively alkylated at position 2a with 1,4-dibromobutane (V) in the presence of NaH to provide the bromobutyl derivative (VI).Then,condensation of bromide (VI) with amine (III) employing K2CO3 in DMF leads to the title compound.
参考文献标题:2a-[4-(Tetrahydropyridondol-2-yl)butyl]tetrahydrobenzindole derivatives: New selective antagonists of the 5-hydroxytryptamine7 receptor
文献作者:Kikuchi,C.; Ando,T.; Watanabe,T.; Nagaso,H.; Okuno,M.; Hiranuma,T.; Koyama,M.
参考来源:J Med Chem 2002,45(11),2197