(2S)-2-amino-5-([(1R)-2-[(carboxymethyl)amino]-1-[([[4-chloro(hydroxy)anilino]carbonyl]sulfanyl)methyl]-2-oxoethyl]amino)-5-oxopentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】29437

【品名】(2S)-2-amino-5-([(1R)-2-[(carboxymethyl)amino]-1-[([[4-chloro(hydroxy)anilino]carbonyl]sulfanyl)methyl]-2-oxoethyl]amino)-5-oxopentanoic acid

【CA登记号】

【分子式】C₁₇H₂₁ClN₄O₈S

【分子量】476.8946

【元素组成】C 42.82% H 4.44% Cl 7.43% N 11.75% O 26.84% S 6.72%

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：(V)

Treatment of 4-chlorophenyl chloroformate (I) with N-(4-chlorophenyl) hydroxylamine (II) produced the N-hydroxycarbamate (III). This was condensed with glutathione (IV) to afford thiocarbamate (V). Finally, both carboxylate groups of (V) were esterified in ethanolic HCl to provide the target diethyl ester.

参考文献中间体

合成目标

【1】 Sentz, D.L.; Kavarana, M.J.; O'Neill, H.B.; Wang, H.; Eiseman, J.L.; Sharkey, E.M.; Creighton, D.J.; Pharmacokinetics and antitumor properties in tumor-bearing mice of an enediol analogue inhibitor of glyoxalase I. Cancer Chemotherapy and Pharmacology 2000, 46, 2, 156.
【2】 Kavarana, M.J.; Kovaleva, E.G.; Creighton, D.J.; Wollman, M.B.; Eiseman, J.L.; Mechanism-based competitive inhibitors of glyoxalase I: Intracellular delivery, in vitro antitumor activities, and stabilities in human serum and mouse serum. J Med Chem 1999, 42, 2, 221.
【3】 Muthy, N.S.R.K.; et al.; S-(N-Aryl-N-hydroxycarbamoyl)glutathione derivatives are tight-binding inhibitors of Glyoxalase I and Slow Substrates for Glyoxalase II. J Med Chem 1994, 37, 14, 2161-2166.
【4】 Creighton, D.J.; Hamilton, D.S. (University of Maryland); Glutathione N-hydroxycarbamoyl thioesters and method of inhibiting neoplastic growth. US 5616563; WO 9600061 .

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)	17779	1-chloro-4-[(chlorocarbonyl)oxy]benzene	7693-45-0	C₇H₄Cl₂O₂	详情	详情
(II)	29435	1-chloro-4-(hydroxyamino)benzeneN-(4-chlorophenyl)hydroxylamine		C₆H₆ClNO	详情	详情
(III)	29438	4-chlorophenyl 4-chlorophenyl(hydroxy)carbamate		C₁₃H₉Cl₂NO₃	详情	详情
(IV)	29436	(2S)-2-amino-5-[[(1R)-2-[(carboxymethyl)amino]-2-oxo-1-(sulfanylmethyl)ethyl]amino]-5-oxopentanoic acid	70-18-8	C₁₀H₁₇N₃O₆S	详情	详情
(V)	29437	(2S)-2-amino-5-([(1R)-2-[(carboxymethyl)amino]-1-[([[4-chloro(hydroxy)anilino]carbonyl]sulfanyl)methyl]-2-oxoethyl]amino)-5-oxopentanoic acid		C₁₇H₂₁ClN₄O₈S	详情	详情

Extended Information