(4S)-4-ethyl-4-hydroxy-11-methyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione -Drug Synthesis Database

【结构式】

【分子编号】42506

【品名】(4S)-4-ethyl-4-hydroxy-11-methyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

【CA登记号】

【分子式】C₂₁H₁₈N₂O₄

【分子量】362.385

【元素组成】C 69.6% H 5.01% N 7.73% O 17.66%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XII)

Semisynthesis: Treatment of camptothecin (XI) with tert-butylhydroperoxide in the presence of FeSO4, conc. H2SO4 and acetic acid in water gives (S)-7-methylcamptothecin (XII). Mannich reaction of compound (XII) with isopropylamine hydrochloride in DMSO as a formaldehyde source gives CKD-602.

参考文献中间体

合成目标

【1】 Hong, C.I.; Kim, J.K.; Ahn, S.K.; CKD-602. Drugs Fut 2000, 25, 12, 1243.
【2】 Kim, K.K.; Kim, J.W.; Journ, D.J.; Jeong, B.S.; Choi, N.S.; Hong, C.I.; Ahn, S.K.; Kim, J.K.; Lee, S.J.; Jew, S.-S.; Practical synthesis of (S)-7-(2-isopropylamino)ethylcamptothecin hydrochloride, potent topoisomerase I inhibitor. J Heterocycl Chem 2000, 37, 1141.
【3】 Miyasaka, T.; Nokata, K.; Furuta, T.; Yokokura, T.; Sawada, S.; Chemical modification of an antitumor alkaloid camptothecin: Synthesis and antitumor activity of 7-C-substituted camptothecins. Chem Pharm Bull 1991, 39, 10, 2574.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	10816	Camptothecin; (4S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 4-et-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo(b,h)fluorene-3,13-dione	7689-03-4	C₂₀H₁₆N₂O₄	详情	详情
(XII)	42506	(4S)-4-ethyl-4-hydroxy-11-methyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione		C₂₁H₁₈N₂O₄	详情	详情

Extended Information