(2S)-2-[(2-chlorophenyl)methoxycarbonylamino]-3-methylbutanoic acid | 301346-05-4

• 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-[(2-chlorophenyl)methoxycarbonylamino]-3-methylbutanoic acid
• CAS: 301346-05-4
• 化学式: C₁₃H₁₆ClNO₄
• 分子量: 285.727
• InChiKey: RRVMQJCRVFCJKO-NSHDSACASA-N

物化性质

• 沸点：
  458.8±35.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-[(2-chlorophenyl)methoxycarbonylamino]-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 作用下， 生成 3-[(S)-2-(2-Chloro-benzyloxycarbonylamino)-3-methyl-butyrylamino]-5-fluoro-4-oxo-pentanoic acid tert-butyl ester
  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：

  邻氯苄醇 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 生成 (2S)-2-[(2-chlorophenyl)methoxycarbonylamino]-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
• 作为试剂：
  描述：

  对氯扁桃酸 在 (2S)-2-[(2-chlorophenyl)methoxycarbonylamino]-3-methylbutanoic acid 作用下， 以 aq. phosphate buffer 、 二氯甲烷 为溶剂， 生成 (R)-2-(4-氯苯基)-2-羟基乙酸 、 L-对氯扁桃酸{S-(+)-对氯扁桃酸、S-(+)-4-氯扁桃酸}
  参考文献：
  名称：

  通过使用2-氯-N-羰基苄氧基-L-氨基酸进行液-液萃取，对4-氯扁桃酸的对映选择性拆分。

  摘要：

  使用2-氯-N-羰基苄氧基-L-氨基酸（2-Cl-Z-AA）作为手性萃取剂，研究了4-氯扁桃酸（4-ClMA）的液-液萃取分离度。研究了影响萃取效率的重要因素，包括手性萃取剂的类型，水相的pH值，有机相中手性萃取剂的初始浓度，水相中4-ClMA的初始浓度和分离温度。观察到，由于（R）-4-ClMA和2−之间形成的配合物具有更高的稳定性，因此有机相中（R）-4-ClMA的浓度比（S）-4-ClMA的浓度高得多。 Cl‐Z‐AA。在0.02 mol / L的2-Cl-Z-缬氨酸溶于二氯甲烷，pH为2.0、4-ClMA的浓度为0.11 mmol / L和T为296.7K的条件下，分离系数（α）为3.05。

  DOI：

  10.1002/chir.22738

文献信息

• Caspase inhibitors and the use thereof
  申请人：Cytovia, Inc.

  公开号：US20040116355A1

  公开（公告）日：2004-06-17

  The present invention is directed to novel dipeptide thereof, represented by the general Formula I: 1 where R 1 -R 3 , 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.

  本发明涉及一种新颖的二肽，其由一般化学式I表示：1其中R1-R3，X和Y在此定义。本发明还涉及发现，具有I式化合物的化合物是半胱天冬酶和细胞凋亡的有效抑制剂。因此，本发明的抑制剂可以延缓或阻止在细胞、组织或整个器官丢失的各种临床情况中的细胞死亡。
• CASPASE INHIBITORS AND THE USE THEREOF
  申请人：Cytovia, Inc.

  公开号：EP1177168B1

  公开（公告）日：2007-05-30
• 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
• US6355618B1
  申请人：——

  公开号：US6355618B1

  公开（公告）日：2002-03-12