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【结 构 式】

【药物名称】

【化学名称】4-Nitro-N-[1,2,3-tris(acetyloxy)-5,6,7,9-tetrahydro-10- (methylsulfanyl)-9-oxobenzo[a]heptalen-7(S)-yl]- benzamide

【CA登记号】

【 分 子 式 】C30H26N2O10S

【 分 子 量 】606.61312

【开发单位】Natl. Cancer Inst., Frederick, MD (US); Univ. North Carolina, Chapel Hill, NC (US)

【药理作用】ONCOLYTIC DRUGS,DNA-INTERCALATING DRUGS

合成路线1

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.

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