4-nitro-N-[(7S)-1,2,3-trihydroxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]benzamide -Drug Synthesis Database

【结构式】

【分子编号】18484

【品名】4-nitro-N-[(7S)-1,2,3-trihydroxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]benzamide

【CA登记号】

【分子式】C₂₄H₂₀N₂O₇S

【分子量】480.49808

【元素组成】C 59.99% H 4.2% N 5.83% O 23.31% S 6.67%

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：(VI)

Thiocolchicine (II) was prepared from colchicine (I) by treatment with sodium methylthiolate. Then, hydrolysis of acetamide group with methanolic HCl afforded deacetyl thiocolchicine (III). Subsequent acylation with p-nitrobenzoyl chloride (IV) in the presence of pyridine provided amide (V), which was demethylated with excess BBr3 to give the corresponding triphenol (VI). Finally, esterification with acetyl chloride in the presence of pyridine and 4-(dimethylamino)pyridine furnished the target triacetate.

参考文献中间体

合成目标

【1】 Guan, J.; et al.; Antitumor agents. 185. Synthesis and biological evaluation of tridemethylthiocolchicine analogues as novel topoisomerase II inhibitors. J Med Chem 1998, 41, 11, 1956.

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)	18479	N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide	64-86-8	C₂₂H₂₅NO₆	详情	详情
(II)	18480	N-[(7S)-1,2,3-trimethoxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide		C₂₂H₂₅NO₅S	详情	详情
(III)	18481	(7S)-7-amino-1,2,3-trimethoxy-10-(methylsulfanyl)-6,7-dihydrobenzo[a]heptalen-9(5H)-one		C₂₀H₂₃NO₄S	详情	详情
(IV)	18941	p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride	122-04-3	C₇H₄ClNO₃	详情	详情
(V)	18483	4-nitro-N-[(7S)-1,2,3-trimethoxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]benzamide		C₂₇H₂₆N₂O₇S	详情	详情
(VI)	18484	4-nitro-N-[(7S)-1,2,3-trihydroxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]benzamide		C₂₄H₂₀N₂O₇S	详情	详情

Extended Information