Methyl 2(R)-(1(S)-carboxy-3-phenylpropylamino)-4-(p-toluenesulfonylamino)butyrate | 184685-22-1

• 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: Methyl 2(R)-(1(S)-carboxy-3-phenylpropylamino)-4-(p-toluenesulfonylamino)butyrate
• 英文别名: (2S)-2-[[(2R)-1-methoxy-4-[(4-methylphenyl)sulfonylamino]-1-oxobutan-2-yl]amino]-4-phenylbutanoic acid
• CAS: 184685-22-1
• 化学式: C₂₂H₂₈N₂O₆S
• 分子量: 448.54
• InChiKey: AKRGYVOVFSMMPU-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 2(R)-(1(S)-carboxy-3-phenylpropylamino)-4-(p-toluenesulfonylamino)butyrate 在 lithium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-2-[(S)-1-((S)-3-Methyl-1-phenylcarbamoyl-butylcarbamoyl)-3-phenyl-propylamino]-4-(toluene-4-sulfonylamino)-butyric acid
  参考文献：
  名称：

  Potent matrix metalloproteinase inhibitors: Amino-carboxylate compounds containing modifications of the P1 residue

  摘要：

  A series of amino-carboxylate inhibitors of matrix metalloproteinases containing different p1 modifications have been synthesized. It was discovered that a toluenesulfonamide-type substituent at the P1 position considerably enhances the binding affinity of inhibitors for stromelysin. Replacements of the P2'-P3' residues with nonpeptide components result in loss of inhibitory activity.

  DOI：

  10.1016/0960-894x(96)00028-5
• 作为产物：
  描述：

  (R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-cyanopropanoate 在 palladium on activated charcoal 盐酸 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 生成 Methyl 2(R)-(1(S)-carboxy-3-phenylpropylamino)-4-(p-toluenesulfonylamino)butyrate
  参考文献：
  名称：

  Potent matrix metalloproteinase inhibitors: Amino-carboxylate compounds containing modifications of the P1 residue

  摘要：

  A series of amino-carboxylate inhibitors of matrix metalloproteinases containing different p1 modifications have been synthesized. It was discovered that a toluenesulfonamide-type substituent at the P1 position considerably enhances the binding affinity of inhibitors for stromelysin. Replacements of the P2'-P3' residues with nonpeptide components result in loss of inhibitory activity.

  DOI：

  10.1016/0960-894x(96)00028-5

文献信息

• US5703092A
  申请人：——

  公开号：US5703092A

  公开（公告）日：1997-12-30
• Potent matrix metalloproteinase inhibitors: Amino-carboxylate compounds containing modifications of the P1 residue
  作者：Chu-Biao Xue、Xiaohua He、John Roderick、William F. DeGrado、Carl Decicco、Robert A. Copeland

  DOI：10.1016/0960-894x(96)00028-5

  日期：1996.2

  A series of amino-carboxylate inhibitors of matrix metalloproteinases containing different p1 modifications have been synthesized. It was discovered that a toluenesulfonamide-type substituent at the P1 position considerably enhances the binding affinity of inhibitors for stromelysin. Replacements of the P2'-P3' residues with nonpeptide components result in loss of inhibitory activity.