(2S)-2-(cyclopentylmethoxycarbonylamino)-3-methylbutanoic acid | 797057-80-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-(cyclopentylmethoxycarbonylamino)-3-methylbutanoic acid
• CAS: 797057-80-8
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: IVGGNWKTBGKIBN-JTQLQIEISA-N

物化性质

• 沸点：
  400.3±28.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-(cyclopentylmethoxycarbonylamino)-3-methylbutanoic acid 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 生成 3-((S)-2-Cyclopentylmethoxycarbonylamino-3-methyl-butyrylamino)-5-fluoro-4-oxo-pentanoic acid
  参考文献：
  名称：

  Dipeptidyl aspartyl fluoromethylketones as potent caspase inhibitors: SAR of the N-protecting group

  摘要：

  This article describes the synthesis and biological evaluation of a group of N-protected Val-Asp-fmk as caspase inhibitors. The protecting group was found to contribute to caspase-3 inhibiting activity, and compounds with a large group such as Cbz are more active than compounds with a small group such as Ac. Compounds with more hydrophobic protecting groups were found to be more active in cell apoptosis protection assays, probably due to increased cell permeability. MX1122,2,4-di-Cl-Cbz-Val-Aspfmk, is identified as a potent broad-spectrum caspase inhibitor and is selective for caspases versus other proteases, with good activity in the cell apoptosis protection assays as well as good efficacy in the mouse liver apoptosis model. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.027
• 作为产物：
  描述：

  环戊基甲醇 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 生成 (2S)-2-(cyclopentylmethoxycarbonylamino)-3-methylbutanoic acid
  参考文献：
  名称：

  Dipeptidyl aspartyl fluoromethylketones as potent caspase inhibitors: SAR of the N-protecting group

  摘要：

  This article describes the synthesis and biological evaluation of a group of N-protected Val-Asp-fmk as caspase inhibitors. The protecting group was found to contribute to caspase-3 inhibiting activity, and compounds with a large group such as Cbz are more active than compounds with a small group such as Ac. Compounds with more hydrophobic protecting groups were found to be more active in cell apoptosis protection assays, probably due to increased cell permeability. MX1122,2,4-di-Cl-Cbz-Val-Aspfmk, is identified as a potent broad-spectrum caspase inhibitor and is selective for caspases versus other proteases, with good activity in the cell apoptosis protection assays as well as good efficacy in the mouse liver apoptosis model. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.027

文献信息

• CASPASE INHIBITORS AND THE USE THEREOF
  申请人：Cytovia, Inc.

  公开号：EP1177168A1

  公开（公告）日：2002-02-06
• EP1177168A4
  申请人：——

  公开号：EP1177168A4

  公开（公告）日：2003-06-25
• CASPASE INHIBITORS FOR THE TREATMENT OF DISEASES AND CONDITIONS CAUSED BY EXPOSURE TO RADIONUCLIDES, BIOLOGICAL AGENTS, OR CHEMICAL AGENTS
  申请人：Cytovia, Inc.

  公开号：EP1494700A2

  公开（公告）日：2005-01-12
• [EN] CASPASE INHIBITORS AND THE USE THEREOF<br/>[FR] INHIBITEURS DE LA CASPASE ET LEUR UTILISATION
  申请人：CYTOVIA INC

  公开号：WO2000061542A1

  公开（公告）日：2000-10-19

  The present invention is directed to novel dipeptide thereof, represented by general formula (I): where R1-R3, X and Y are defined herein. The present invention also relates to the discovery that compounds having Formula (I) are potent inhibitors of caspases and apoptotic cell death. Therefore, the inhibitors of this invention can retard or block cell death in a variety of clinical conditions in which the loss of cells, tissues or entire organs occurs.
• [EN] CASPASE INHIBITORS FOR THE TREATMENT OF DISEASES AND CONDITIONS CAUSED BY EXPOSURE TO RADIONUCLIDES, BIOLOGICAL AGENTS, OR CHEMICAL AGENTS<br/>[FR] INHIBITEURS DE CASPASES POUR LE TRAITEMENT DE MALADIES ET D'ETATS PATHOLOGIQUES DUS A UNE EXPOSITION A DES RADIONUCLEIDES, A DES AGENTS BIOLOGIQUES OU A DES AGENTS CHIMIQUES
  申请人：CYTOVIA INC

  公开号：WO2004002401A2

  公开（公告）日：2004-01-08

  The use of caspase inhibitors for treating cell death induced by radionuclides, biological agents, or chemical agents is disclosed. In particular, treatment of diseases or conditions caused by exposure to radionuclides, biological agents, or chemical agents, spread of radionuclides, biological agents, or chemical agents, explosion of radionuclides, biological agents, or chemical agents by terrorists or accidental exposure to radionuclides, biological agents, or chemical agents from a nuclear power plant, manufacturing or processing plant, research facility, or hospital is disclosed.