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【结 构 式】

【药物名称】TSRI-265

【化学名称】N1,N3-Bis[2-[5(S)-carboxy-5-[4-(trifluoromethyl)benzyloxycarboxamido]pentylamino]-2-oxoethyl]benzene-1,3-dicarboxamide

【CA登记号】

【 分 子 式 】C42H46F6N6O12

【 分 子 量 】940.85832

【开发单位】Scripps Research Institute (Originator)

【药理作用】Oncolytic Drugs, Angiogenesis Inhibitors

合成路线1

Reaction of 4-(trifluoromethyl)benzyl alcohol (I) with DSC followed by coupling with partially protected lysine (II) affords carbamate (III), which is converted into derivative (V) first by Boc removal with HCl/dioxane in dichloromethane followed by coupling with Boc-Gly-OH (IV) by means of EDCl and DIEA. Boc removal of compound (V) with HCl/dioxane in dichloromethane, followed by condensation with isophthaloyl dichloride (VI) by means of DIEA in DMF, gives compound (VII), which is finally subjected to methyl ester saponification with LiOH in THF/MeOH to provide the desired product.

1 Boger, D.L.; et al.; Identification of a novel class of small-molecule antiangiogenic agents through the screening of combinatorial libraries which function by inhibiting the binding and localization of proteinase MMP2 to integrin alphavbeta3. J Am Chem Soc 2001, 123, 7, 1280.
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) 47327 [4-(trifluoromethyl)phenyl]methanol 349-95-1 C8H7F3O 详情 详情
(II) 47328 methyl (2S)-2-amino-6-[(tert-butoxycarbonyl)amino]hexanoate C12H24N2O4 详情 详情
(III) 47329 methyl (2S)-6-[(tert-butoxycarbonyl)amino]-2-[([[4-(trifluoromethyl)benzyl]oxy]carbonyl)amino]hexanoate C21H29F3N2O6 详情 详情
(IV) 18066 N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid 4530-20-5 C7H13NO4 详情 详情
(V) 47330 methyl (2S)-6-([2-[(tert-butoxycarbonyl)amino]acetyl]amino)-2-[([[4-(trifluoromethyl)benzyl]oxy]carbonyl)amino]hexanoate C23H32F3N3O7 详情 详情
(VI) 12501 Isophthaloyl dichloride 99-63-8 C8H4Cl2O2 详情 详情
(VII) 47331 methyl (2S)-6-([2-[(3-[(10S)-10-(methoxycarbonyl)-4,12-dioxo-14-[4-(trifluoromethyl)phenyl]-13-oxa-2,5,11-triazatetradec-1-anoyl]benzoyl)amino]acetyl]amino)-2-[([[4-(trifluoromethyl)benzyl]oxy]carbonyl)amino]hexanoate C44H50F6N6O12 详情 详情
Extended Information