Ethyl L-3-trans-(2-phenylethylcarbamoyl)oxirane-2-carboxylate | 192815-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: Ethyl L-3-trans-(2-phenylethylcarbamoyl)oxirane-2-carboxylate
• CAS: 192815-59-1
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: VFOFWDSZUCGPQL-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Ethyl L-3-trans-(2-phenylethylcarbamoyl)oxirane-2-carboxylate 在 氢氧化钾 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (S)-4-Benzyloxycarbonylamino-4-{(S)-1-[N'-tert-butoxycarbonylmethyl-N'-((2S,3S)-3-phenethylcarbamoyl-oxiranecarbonyl)-hydrazinocarbonyl]-2-methyl-propylcarbamoyl}-butyric acid tert-butyl 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)-3-(乙氧羰基)环氧乙烷-2-羧酸 、 2-苯乙胺 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 作用下， 以 氯仿 为溶剂， 反应 17.0h， 生成 Ethyl L-3-trans-(2-phenylethylcarbamoyl)oxirane-2-carboxylate
  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

• Epoxysuccinamide derivative or salt thereof, and medicine comprising the
  申请人：Taiho Pharmaceutical Co., Ltd.

  公开号：US05883121A1

  公开（公告）日：1999-03-16

  The invention relates an epoxysuccinamide derivative represented by the general formula (1) ##STR1## wherein R.sup.1 and R.sup.2 are the same or different from each other and independently represent H or an aromatic hydrocarbon group or aralkyl group which may be substituted, or R.sup.1 and R.sup.2 may form a nitrogen-containing heterocyclic ring together with the adjacent nitrogen atoms, R.sup.3 is H or an acyl group, R.sup.4 is H or an aralkyl group, and R.sup.5 is an aromatic hydrocarbon group or aralkyl group which may be substituted, or R.sup.5 may form an amino acid residue, which may be protected, together with the adjacent nitrogen atom, or a salt thereof, and a medicine comprising the derivative as an active ingredient; and this compound has an inhibiting activity against cathepsin, and particularly, specifically inhibits cathepsin L and is hence useful for prevention and treatment of osteopathy such as osteoporosis.

  该发明涉及一种由一般式(1)表示的环氧琥珀酰胺衍生物 ##STR1## 在该式中，R.sup.1和R.sup.2相同或不同，分别代表H或芳香烃基或芳基烷基，可以被取代，或R.sup.1和R.sup.2可以与相邻氮原子一起形成含氮杂环，R.sup.3为H或酰基，R.sup.4为H或芳基烷基，R.sup.5为芳香烃基或芳基烷基，可以被取代，或R.sup.5可以与相邻氮原子一起形成氨基酸残基，可以被保护，或其盐，以及包含该衍生物作为活性成分的药物；该化合物对半胱氨酸蛋白酶具有抑制活性，特别是特异性抑制半胱氨酸蛋白酶L，因此对于预防和治疗骨病如骨质疏松症非常有用。