S-30972-1
Chemical Name: 9-(4-Carboxybutyryloxy)-N-[2-(dimethylamino)ethyl]-5,6-dimethyl-6H-pyrido[4,3-b]carbazole-1-carboxamide dihydrochloride; Pentanedioic acid [1-[N-[2-(dimethylamino)ethyl]carbamoyl]-5,6-dimethyl-6H-pyrido[4,3-b]carbazole-9-yl] monoester dihydrochloride
CAS No. 209617-63-0, 209617-97-0 (free base)
项目整合开发状态: Preclinical
项目研究机构: Servier (Originator)
合成路线:The title hemiglutarate ester was synthesized by acylation of the known olivacine derivative (I) with glutaric anhydride (II) in pyridine,followed by conversion to the corresponding dihydrochloride salt.
📌 参考资料/链接：
参考文献标题:Ellipticine derivs.,their preparation and pharmaceutical compsns.containing them
文献作者:Guilbaud,N.; Bisagni,E.; Guillonneau,C.; Charton,Y.; Atassi,G.; Pierre,A.(ADIR et Cie.)
参考来源:EP 0850940; US 6162811
📄 详细内容
合成路线:The title hemiglutarate ester was synthesized by acylation of the known olivacine derivative (I) with glutaric anhydride (II) in pyridine,followed by conversion to the corresponding dihydrochloride salt.
合成路线:The known pyridocarbazole (I) was methylated to (II) using dimethyl carbonate as the alkylating agent in the presence of K2CO3 and the phase-transfer catalyst adogen-464.For the preparation of the required amide (V),the ester group of (III) was first hydrolyzed with NaOH to the carboxylic acid (III),which was then coupled with 2-(dimethylamino)ethyl amine (IV) by means of (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) in hot N-methylpyrrolidone yielding (V).Finally,cleavage of the methyl ether of (V) with BBr3 provided the title compound.
参考文献标题:Synthesis of 9-O-substituted derivatives of 9-hydroxy-5,6-dimethyl-6H-pyrido[4,3-b]carbazole-1-carboxylic acid (2-(dimethylamino)ethyl)amide and their 10- and 11-methyl analogues with improved antitumor activity
文献作者:Guillonneau,C.; Pierre,A.; Charton,Y.; Guilbaud,N.; Kraus-Berthier,L.; Leonce,S.; Michel,A.; Bisagni,E.; Atassi,G.
参考来源:J Med Chem 1999,42(12),2191
产品链接: CAS No. 209617-63-0››