(4S)-12-ethoxy-4-ethyl-4,9-dihydroxy-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】38994

【品名】(4S)-12-ethoxy-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

【CA登记号】

【分子式】C₂₂H₂₀N₂O₆

【分子量】408.41068

【元素组成】C 64.7% H 4.94% N 6.86% O 23.5%

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：(II)

Treatment of 10-hydroxycamptothecin (I) with EtOH and H2SO4 in the presence of FeCl3 produced 5-ethoxy-10-hydroxycamptothecin (II) along with minor amounts of the 5-hydroxy derivative (III). Hydrolysis of (II) to give (III) was effected using HCl in H2O-EtOH. Finally, acid-catalyzed condensation of (III) with 2,2,2-trifluoroethanol furnished the title compound.

参考文献中间体

合成目标

【1】 Subrahmanyam, D.; Sarma, V.M.; Venkateswarlu, A.; et al.; Novel C-ring analogues of 20(S)-camptothecin. Part 3: Synthesis and their in vitro cytotoxicity of A-, B- and C-ring analogues. Bioorg Med Chem Lett 2000, 10, 4, 369.
【2】 Bitonti, A.; Woessner, R.; Peyman, A.; Uhlmann, E. (Aventis Pharma Deutschland GmbH); Short oligonucleotides for the inhibition of VEGF expression. EP 0979869; WO 0008141 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	19483	2,2,2-trifluoro-1-ethanol	75-89-8	C₂H₃F₃O	详情	详情
(I)	13340	(4S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 7-Ethyl-10-hydroxycamptothecin	86639-52-3	C₂₀H₁₆N₂O₅	详情	详情
(II)	38994	(4S)-12-ethoxy-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione		C₂₂H₂₀N₂O₆	详情	详情
(III)	38995	(4S)-4-ethyl-4,9,12-trihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione		C₂₀H₁₆N₂O₆	详情	详情

Extended Information