-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】2,3,7,8,9,11-Hexahydro-1H-pyrrolo[1,2-a]pyrrolo[1',2':1,2]imidazo[4,5-f]benzimidazole-5,10-dione

【CA登记号】

【分子式】C₁₄H₁₂N₄O₂

【分子量】268.27734

【开发单位】Arizona State University (Originator)

【药理作用】ONCOLYTIC DRUGS, DNA Topoisomerase II Inhibitors, DNA-Intercalating Drugs

合成路线1

Treatment of 1,5-dibromo-2,4-dinitrobenzene (I) with pyrrolidine (II) afforded dipyrrolidino derivative (III). Reduction of the nitro groups of (III) by catalytic hydrogenation, followed by acetylation of amine (IV) provided diamide (V). Oxidative cyclization of (V) using H2O2 in the presence of formic acid gave rise to the dipyrroloimidazobenzimidazole system (VI). Quinone elaboration involved nitration of (VI) to (VII), nitro group reduction to amine (VIII), and finally amine oxidation employing Fremy's salt.

参考文献中间体

【1】 Skibo, E.B.; Schulz, W.G.; Inhibitors of topoisomerase II based on the benzodiimidazole and dipyrroloimidazobenzimidazole ring systems: Controlling DT-diaphorase reductive inactivation with steric bulk. J Med Chem 2000, 43, 4, 629.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	39236	1,5-dibromo-2,4-dinitrobenzene		C₆H₂Br₂N₂O₄	详情	详情
(II)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(III)	39237	1-[2,4-dinitro-5-(1-pyrrolidinyl)phenyl]pyrrolidine		C₁₄H₁₈N₄O₄	详情	详情
(IV)	39238	4,6-di(1-pyrrolidinyl)-1,3-benzenediamine; 5-amino-2,4-di(1-pyrrolidinyl)phenylamine		C₁₄H₂₂N₄	详情	详情
(V)	39239	N-[5-(acetamido)-2,4-di(1-pyrrolidinyl)phenyl]acetamide		C₁₈H₂₆N₄O₂	详情	详情
(VI)	39240	2,3,8,9-tetrahydro-1H,7H-pyrrolo[1,2-a]pyrrolo[1',2':1,2]imidazo[4,5-f]benzimidazole		C₁₄H₁₄N₄	详情	详情
(VII)	39241	5-nitro-2,3,8,9-tetrahydro-1H,7H-pyrrolo[1,2-a]pyrrolo[1',2':1,2]imidazo[4,5-f]benzimidazole		C₁₄H₁₃N₅O₂	详情	详情
(VIII)	39242	2,3,8,9-tetrahydro-1H,7H-pyrrolo[1,2-a]pyrrolo[1',2':1,2]imidazo[4,5-f]benzimidazol-5-ylamine; 2,3,8,9-tetrahydro-1H,7H-pyrrolo[1,2-a]pyrrolo[1',2':1,2]imidazo[4,5-f]benzimidazol-5-amine		C₁₄H₁₅N₅	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)