N-[(2S)-3-hydroxy-4-oxo-1-phenyl-4-(2-phenylethylamino)butan-2-yl]-3-methyl-6-oxo-1H-pyridine-2-carboxamide | 1197334-31-8

• 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: N-[(2S)-3-hydroxy-4-oxo-1-phenyl-4-(2-phenylethylamino)butan-2-yl]-3-methyl-6-oxo-1H-pyridine-2-carboxamide
• CAS: 1197334-31-8
• 化学式: C₂₅H₂₇N₃O₄
• 分子量: 433.507
• InChiKey: DIMOHFBBAJQRNT-AJZOCDQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(2S)-3-hydroxy-4-oxo-1-phenyl-4-(2-phenylethylamino)butan-2-yl]-3-methyl-6-oxo-1H-pyridine-2-carboxamide 在 戴斯-马丁氧化剂 作用下， 以58%的产率得到(S)-N-(3,4-dioxo-4-(phenethylamino)-1-phenylbutan-2-yl)-3-methyl-6-oxo-1,6-dihydropyridine-2-carboxamide
  参考文献：
  名称：

  Design and synthesis of calpain inhibitory 6-pyridone 2-carboxamide derivatives

  摘要：

  Excessive calpain activation contributes to serious cellular damage in many pathological conditions. The involvement of mu-calpain in neurological disorders such as, stroke and Alzheimer's disease has attracted considerable interest in the use of calpain inhibitors as therapeutic agents. 6-Pyridone 2-carboxamides derived from ketoamides were synthesized as conformationally constrained structures resembling the well known peptidic mu-calpain inhibitor, MDL 28,170, and their mu-calpain inhibitory activities were evaluated. Of the compounds synthesized, compound 2a, which has a primary amide at warhead region of the inhibitor most potently inhibited mu-calpain with an IC50 value of 2.81 +/- 1.26 mu M, which is ca. 40-fold less than that of MDL 28,170. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.023
• 作为产物：
  描述：

  6-羟基-3-甲基吡啶-2-羧酸 、 3(S)-3-amino-2(RS)-hydroxy-N-phenethyl-4-phenylbutanamide 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 四氢呋喃 、 二氯甲烷 为溶剂， 以42%的产率得到N-[(2S)-3-hydroxy-4-oxo-1-phenyl-4-(2-phenylethylamino)butan-2-yl]-3-methyl-6-oxo-1H-pyridine-2-carboxamide
  参考文献：
  名称：

  Design and synthesis of calpain inhibitory 6-pyridone 2-carboxamide derivatives

  摘要：

  Excessive calpain activation contributes to serious cellular damage in many pathological conditions. The involvement of mu-calpain in neurological disorders such as, stroke and Alzheimer's disease has attracted considerable interest in the use of calpain inhibitors as therapeutic agents. 6-Pyridone 2-carboxamides derived from ketoamides were synthesized as conformationally constrained structures resembling the well known peptidic mu-calpain inhibitor, MDL 28,170, and their mu-calpain inhibitory activities were evaluated. Of the compounds synthesized, compound 2a, which has a primary amide at warhead region of the inhibitor most potently inhibited mu-calpain with an IC50 value of 2.81 +/- 1.26 mu M, which is ca. 40-fold less than that of MDL 28,170. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.023

文献信息

• Design and synthesis of calpain inhibitory 6-pyridone 2-carboxamide derivatives
  作者：Ki Yong Lee、Kwang Seob Lee、Changbae Jin、Yong Sup Lee

  DOI：10.1016/j.ejmech.2008.02.023

  日期：2009.3

  Excessive calpain activation contributes to serious cellular damage in many pathological conditions. The involvement of mu-calpain in neurological disorders such as, stroke and Alzheimer's disease has attracted considerable interest in the use of calpain inhibitors as therapeutic agents. 6-Pyridone 2-carboxamides derived from ketoamides were synthesized as conformationally constrained structures resembling the well known peptidic mu-calpain inhibitor, MDL 28,170, and their mu-calpain inhibitory activities were evaluated. Of the compounds synthesized, compound 2a, which has a primary amide at warhead region of the inhibitor most potently inhibited mu-calpain with an IC50 value of 2.81 +/- 1.26 mu M, which is ca. 40-fold less than that of MDL 28,170. (C) 2008 Elsevier Masson SAS. All rights reserved.