(S)-3-(4-((2H-tetrazol-5-yl)methyl)phenyl)-2-acetamidopropanoic acid | 945979-99-7

• 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: (S)-3-(4-((2H-tetrazol-5-yl)methyl)phenyl)-2-acetamidopropanoic acid
• CAS: 945979-99-7
• 化学式: C₁₃H₁₅N₅O₃
• 分子量: 289.294
• InChiKey: OGNPHGHZNYFOHM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.08
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  120.86
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-((2H-tetrazol-5-yl)methyl)phenyl)-2-acetamidopropanoic acid 、 Fmoc-L-脯氨酸 、 Fmoc-Thr-OH 、 Fmoc-L-谷氨酰胺 、 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (S)-2-((2S,3R)-2-((S)-2-((S)-1-((S)-2-((S)-3-(4-((2H-tetrazol-5-yl)methyl)phenyl)-2-acetamidopropanamido)-4-methylpentanoyl)pyrrolidine-2-carboxamido)-5-amino-5-oxopentanamido)-3-hydroxybutanamido)-3-methylbutanoic acid
  参考文献：
  名称：

  New syntheses of tetrazolylmethylphenylalanine and O-malonyltyrosine as pTyr mimetics for the design of STAT3 dimerization inhibitors

  摘要：

  Investigation within the pTyr-binding pocket of the STAT3 SH2 domain led us to develop a novel synthesis of two pTyr mimetics, L-tetrazolylmethylphenylalanine (L-Tmp) and L-O-malonyltyrosine (L-OMT), that were next incorporated in a high affinity ligand of STAT3 SH2 domain. Biological evaluation of peptidomimetics on STAT3 dimerization identified L-OMT as the first non-phosphorus pTyr mimetic so far reported against STAT3 SH2 domain, harboring an activity similar to that of the Pmp-containing reference peptidomimetic. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.107
• 作为产物：
  描述：

  N-((S)-3-(4-(cyanomethyl)phenyl)-1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-1-oxopropan-2-yl)acetamide 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (S)-3-(4-((2H-tetrazol-5-yl)methyl)phenyl)-2-acetamidopropanoic acid
  参考文献：
  名称：

  New syntheses of tetrazolylmethylphenylalanine and O-malonyltyrosine as pTyr mimetics for the design of STAT3 dimerization inhibitors

  摘要：

  Investigation within the pTyr-binding pocket of the STAT3 SH2 domain led us to develop a novel synthesis of two pTyr mimetics, L-tetrazolylmethylphenylalanine (L-Tmp) and L-O-malonyltyrosine (L-OMT), that were next incorporated in a high affinity ligand of STAT3 SH2 domain. Biological evaluation of peptidomimetics on STAT3 dimerization identified L-OMT as the first non-phosphorus pTyr mimetic so far reported against STAT3 SH2 domain, harboring an activity similar to that of the Pmp-containing reference peptidomimetic. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.107