3,3,14-trimethyl-6-(methyloxy)-7-oxo-1-(4-pentenoyloxy)-2,3,7,14-tetrahydro-1H-benzo[b]pyrano[3,2-h]acridin-2-yl 4-pentenoate -Drug Synthesis Database

【结构式】

【分子编号】64870

【品名】3,3,14-trimethyl-6-(methyloxy)-7-oxo-1-(4-pentenoyloxy)-2,3,7,14-tetrahydro-1H-benzo[b]pyrano[3,2-h]acridin-2-yl 4-pentenoate

【CA登记号】

【分子式】C₃₄H₃₅NO₇

【分子量】569.65444

【元素组成】C 71.69% H 6.19% N 2.46% O 19.66%

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：(III)

Dihydroxylation of the benzo[b]pyrano[3,2-h]acridinone derivative (I) by means of N-methylmorpholine-N-oxide in the presence of OsO4 leads to the cis-diol (II), which upon esterification with 4-pentenoyl chloride in pyridine furnishes a mixture of diester (III) and the title mono-pentenoate ester, which can be separated employing flash chromatography.

参考文献中间体

合成目标

【1】 Mai, H.D.T.; Gaslonde, T.; Michel, S.; Tillequin, F.; Koch, M.; Bongui, J.-B.; Elomri, A.; Seguin, E.; Pfeiffer, B.; Renard, P.; David-Cordonnier, M.-H.; Laine, W.; Bailly C.; Kraus-Berthier, L.; Leonce, S.; Hickman, J.A.; Pierre, A.; Structure-activity relationships and mechanism of action of antitumor benzo[b]pyrano[3,2-h]acridin-7-one acronycine analogues. J Med Chem 2003, 46, 14, 3072.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
	61648	4-PENTENOYL CHLORIDE	C₅H₇ClO	详情	详情
(I)	47435	6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one	C₂₄H₂₁NO₃	详情	详情
(II)	47436	(1S,2S)-1,2-dihydroxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one	C₂₄H₂₃NO₅	详情	详情
(III)	64870	3,3,14-trimethyl-6-(methyloxy)-7-oxo-1-(4-pentenoyloxy)-2,3,7,14-tetrahydro-1H-benzo[b]pyrano[3,2-h]acridin-2-yl 4-pentenoate	C₃₄H₃₅NO₇	详情	详情

Extended Information