(2S,3S)-oxirane-2,3-dicarboxylic acid monobenzyl ester | 646532-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-oxirane-2,3-dicarboxylic acid monobenzyl ester
• 英文别名: (2S,3S)-3-phenylmethoxycarbonyloxirane-2-carboxylic acid
• CAS: 646532-92-5
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: MSOZTSXXIISYMG-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-oxirane-2,3-dicarboxylic acid monobenzyl ester 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (2S,3S)-3-(N-Carboxymethyl-N'-{(S)-2-[(S)-3-methyl-2-(3-phenyl-propionylamino)-butyrylamino]-propionyl}-hydrazinocarbonyl)-oxirane-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Aza-Peptide Epoxides as Selective and Potent Inhibitors of Caspases-1, -3, -6, and -8

  摘要：

  Aza-peptide epoxides, a novel class of irreversible protease inhibitors, are specific for the clan CD cysteine proteases. Aza-peptide epoxides with an aza-Asp residue at PI are excellent irreversible inhibitors of caspases-1, -3, -6, and -8 with second-order inhibition rates up to 1910 000 M-1 s(-1). In general, the order of reactivity of aza-peptide epoxides is S'S > R,R > trans > cis. Interestingly, some of the R,R epoxides while being less potent are actually more selective than the S,S epoxides. Our aza-peptide epoxides designed For caspases are stable, potent, and specific inhibitors, as they show little to no inhibition of other proteases such as the aspartyl proteases porcine pepsin, human cathepsin D, plasmepsin 2 from P. falciparum, HIV-1 protease, and the secreted aspartic proteinase 2 (SAP-2) from Candida albicans; the serine proteases granzyme B and alpha-chymotrypsin; and the cysteine proteases cathepsin B and papain (clan CA), and legumain (clan CD).

  DOI：

  10.1021/jm0305016
• 作为产物：
  描述：

  (2S,3S)-oxirane-2,3-dicarboxylic acid 、 苯甲醇 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (2S,3S)-oxirane-2,3-dicarboxylic acid monobenzyl ester
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Aza-Peptide Epoxides as Selective and Potent Inhibitors of Caspases-1, -3, -6, and -8

  摘要：

  Aza-peptide epoxides, a novel class of irreversible protease inhibitors, are specific for the clan CD cysteine proteases. Aza-peptide epoxides with an aza-Asp residue at PI are excellent irreversible inhibitors of caspases-1, -3, -6, and -8 with second-order inhibition rates up to 1910 000 M-1 s(-1). In general, the order of reactivity of aza-peptide epoxides is S'S > R,R > trans > cis. Interestingly, some of the R,R epoxides while being less potent are actually more selective than the S,S epoxides. Our aza-peptide epoxides designed For caspases are stable, potent, and specific inhibitors, as they show little to no inhibition of other proteases such as the aspartyl proteases porcine pepsin, human cathepsin D, plasmepsin 2 from P. falciparum, HIV-1 protease, and the secreted aspartic proteinase 2 (SAP-2) from Candida albicans; the serine proteases granzyme B and alpha-chymotrypsin; and the cysteine proteases cathepsin B and papain (clan CA), and legumain (clan CD).

  DOI：

  10.1021/jm0305016

文献信息

• Aza-peptide epoxides
  申请人：——

  公开号：US20040048327A1

  公开（公告）日：2004-03-11

  The present invention provides compositions for inhibiting proteases, methods for synthesizing the compositions, and methods of using the disclosed protease inhibitors. Aspects of the invention include aza-peptide epoxide compositions that inhibit proteases, for example cysteine proteases, either in vivo or in vitro. The disclosed compounds, pharmaceutically acceptable salts, pharmaceutically acceptable derivatives, prodrugs, or combinations thereof can be used to treat disease or pathological conditions related to the activity of proteases associated with a specific disease or condition. Such treatable conditions include viral infections, stroke, neurodegenerative disease, and inflammatory disease, among others.

  本发明提供了用于抑制蛋白酶的组合物、合成该组合物的方法以及使用所披露的蛋白酶抑制剂的方法。本发明的方面包括抑制蛋白酶（例如半胱氨酸蛋白酶）的氮杂肽环氧化物组合物，无论是在体内还是体外。所披露的化合物、药学上可接受的盐、药学上可接受的衍生物、前药或其组合物可以用于治疗与特定疾病或病况相关的蛋白酶活性相关的疾病或病理条件。这些可治疗的疾病包括病毒感染、中风、神经退行性疾病和炎症性疾病等。
• US4393228A
  申请人：——

  公开号：US4393228A

  公开（公告）日：1983-07-12
• US7056947B2
  申请人：——

  公开号：US7056947B2

  公开（公告）日：2006-06-06
• US8013014B2
  申请人：——

  公开号：US8013014B2

  公开（公告）日：2011-09-06
• [EN] AZA-PEPTIDE EPOXIDES<br/>[FR] EPOXYDES D'AZA-PEPTIDES
  申请人：GEORGIA TECH RES INST

  公开号：WO2004005270A1

  公开（公告）日：2004-01-15

  The present invention provides compositions for inhibiting proteases, methods for synthesizing the compositions, and methods of using the disclosed protease inhibitors. Aspects of the invention include aza-peptide epoxide compositions that inhibit proteases, for example cysteine proteases, either in vivo or in vitro. The disclosed compounds, pharmaceutically acceptable salts, pharmaceutically acceptable derivatives, prodrugs, or combinations thereof can be used to treat disease or pathological conditions related to the activity of proteases associated with a specific disease or condition. Such treatable conditions include viral infections, stroke, neurodegenerative disease, and inflammatory disease, among others.