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【结 构 式】

【药物名称】

【化学名称】N-[3-[N-(4-Cyanobenzyl)-N-[1-(4-cyanobenzyl)-1H-imidazol-5-ylmethyl]aminomethyl]benzoyl]-L-methionine

【CA登记号】245126-51-6

【 分 子 式 】C33H32N6O3S

【 分 子 量 】592.72539

【开发单位】Merck & Co. (Originator)

【药理作用】ONCOLYTIC DRUGS, Farnesyl Transferase Inhibitors, Inhibitors of Signal Transduction Pathways

合成路线1

Amide (III) was prepared by acylation of L-methionine methyl ester (I) with 3-(chloromethyl)benzoyl chloride (II). Displacement of the halogen atom of (III) with LiN3 gave azide (IV), which was reduced to amine (V) by catalytic hydrogenation in the presence of Pd/C. Reductive coupling of (V) with protected imidazole-4-carboxaldehyde (VI) provided the (imidazolylmethyl)amine (VII), and a second reductive coupling of (VII) with benzaldehyde (VIII) furnished the trisubstituted amine (IX). The regioselective imidazole alkylation of (IX) with bromide (X), followed by trityl group deprotection with trifluoroacetic acid yielded (XI). Finally, the methyl ester group of (XI) was hydrolyzed with methanolic NaOH to afford the title carboxylic acid.

1 Ciccarone, T.M.; MacTough, S.C.; Williams, T.M.; et al.; Non-thiol 3-aminomethylbenzamide inhibitor of farnesyl-protein transferase. Bioorg Med Chem Lett 1999, 9, 14, 1991.
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) 17950 D-Methionine methyl ester; methyl (2S)-2-amino-4-(methylsulfanyl)butanoate hydrochloride 21691-49-6 C6H13NO2S 详情 详情
(II) 25107 3-(chloromethyl)benzoyl chloride 63024-77-1 C8H6Cl2O 详情 详情
(III) 33729 methyl (2S)-2-[[3-(chloromethyl)benzoyl]amino]-4-(methylsulfanyl)butanoate C14H18ClNO3S 详情 详情
(IV) 33730 methyl (2S)-2-[[3-(azidomethyl)benzoyl]amino]-4-(methylsulfanyl)butanoate C14H18N4O3S 详情 详情
(V) 33731 methyl (2S)-2-[[3-(aminomethyl)benzoyl]amino]-4-(methylsulfanyl)butanoate C14H20N2O3S 详情 详情
(VI) 27712 1-trityl-1H-imidazole-4-carbaldehyde;1-Tritylimidazole-4-carboxaldehyde 33016-47-6 C23H18N2O 详情 详情
(VII) 33732 methyl (2S)-4-(methylsulfanyl)-2-[[3-([[(1-trityl-1H-imidazol-4-yl)methyl]amino]methyl)benzoyl]amino]butanoate C37H38N4O3S 详情 详情
(VIII) 17552 4-formylbenzonitrile; 4-Cyanobenzaldehyde 105-07-7 C8H5NO 详情 详情
(IX) 33733 methyl (2S)-2-[[3-([(4-cyanobenzyl)[(1-trityl-1H-imidazol-4-yl)methyl]amino]methyl)benzoyl]amino]-4-(methylsulfanyl)butanoate C45H43N5O3S 详情 详情
(X) 14200 4-(Bromomethyl)benzonitrile; alpha-Bromo-p-tolunitrile 17201-43-3 C8H6BrN 详情 详情
(XI) 33734 methyl (2S)-2-([3-[((4-cyanobenzyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)methyl]benzoyl]amino)-4-(methylsulfanyl)butanoate C34H34N6O3S 详情 详情
Extended Information