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【结 构 式】

【药物名称】NSC-D703786, NSC-703786, 5F-DF-203, 5F-203

【化学名称】4-(5-Fluorobenzothiazol-2-yl)-2-methylphenylamine

【CA登记号】260443-89-8

【 分 子 式 】C14H11FN2S

【 分 子 量 】258.31957

【开发单位】National Cancer Institute (Originator), University of Nottingham (Originator)

【药理作用】ONCOLYTIC DRUGS

合成路线1

Jacobsen radical cyclization of thiobenzanilide (I) in the presence of potassium ferricyanide produced a mixture of the desired benzothiazole (III) and minor amounts of its regioisomer (II). An alternative regiospecific synthesis of (III) consisted in the intramolecular cyclization of the ortho-bromo thiobenzanilide (IV) by means of NaH in hot NMP. Further reduction of the nitro group of (III) using SnCl2 in EtOH gave the desired amino compound.

1 Hutchinson, I.; et al.; The regiospecific synthesis of 5- and 7-monosubstituted and 5,6-disubstituted 2-arylbenzothiazoles. Tetrahedron Lett 2000, 41, 3, 425.
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) 46951 N-(3-fluorophenyl)-3-methyl-4-nitrobenzenecarbothioamide C14H11FN2O2S 详情 详情
(II) 46952 7-fluoro-2-(3-methyl-4-nitrophenyl)-1,3-benzothiazole C14H9FN2O2S 详情 详情
(III) 46953 5-fluoro-2-(3-methyl-4-nitrophenyl)-1,3-benzothiazole C14H9FN2O2S 详情 详情
(IV) 46954 N-(2-bromo-5-fluorophenyl)-3-methyl-4-nitrobenzenecarbothioamide C14H10BrFN2O2S 详情 详情

合成路线2

The reaction of 5-fluorobenzothiazol-2-amine (I) with KOH in refluxing water gives the disulfide (II), which is treated with 3-methyl-4-nitrobenzoyl chloride (III) in refluxing pyridine to yield the bis-benzamide (IV). Finally, this compound is reductively cyclized by reaction with SnCl2 and HCl in ethanol/water to afford the target aminophenyl benzothiazole.

1 Chua, M.-S.; Westwell, A.D.; Hutchinson, I.P.; Stevens, M.F.G.; Poole, T.D. (Cancer Research Campaign Technology Ltd.); Substd. 2-arylbenzazole cpds. and their use as antitumour agents. WO 0114354 .
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) 47594 5-fluoro-1,3-benzothiazol-2-amine; 5-fluoro-1,3-benzothiazol-2-ylamine C7H5FN2S 详情 详情
(II) 47595 2-[(2-amino-4-fluorophenyl)disulfanyl]-5-fluoroaniline; 2-[(2-amino-4-fluorophenyl)disulfanyl]-5-fluorophenylamine C12H10F2N2S2 详情 详情
(III) 51998 3-Methyl-4-nitrobenzamide 99584-85-7 C8H8N2O3 详情 详情
(IV) 47597 N-[5-fluoro-2-([4-fluoro-2-[(3-methyl-4-nitrobenzoyl)amino]phenyl]disulfanyl)phenyl]-3-methyl-4-nitrobenzamide C28H20F2N4O6S2 详情 详情
Extended Information