2-[2-(2-羟基-乙基)-苯基氨基]-苯甲酸 | 1026271-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[2-(2-羟基-乙基)-苯基氨基]-苯甲酸
• 英文名称: 2-[2-(2-Hydroxy-ethyl)-phenylamino]-benzoic acid
• 英文别名: 2-[2-(2-Hydroxyethyl)anilino]benzoic acid
• CAS: 1026271-60-2
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: JNPHEWSVEMANER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(2-羟基-乙基)-苯基氨基]-苯甲酸 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-{[2-(2-Hydroxy-ethyl)-phenyl]-oxalyl-amino}-benzoic acid
  参考文献：
  名称：

  Discovery and Structure−Activity Relationship of Oxalylarylaminobenzoic Acids as Inhibitors of Protein Tyrosine Phosphatase 1B

  摘要：

  Protein Tyrosine phosphatase 1B (PTP1B) has been implicated as a key negative regulator of both insulin and leptin signaling pathways. Using an NMR-based screening approach with 15N- and 13C-labeled PTP1B, we have identified 2,3-dimethylphenyloxalylaminobenzoic acid (1) as a general, reversible, and competitive PTPase inhibitor. Structure-based approach guided by X-ray crystallography facilitated the development of 1 into a novel series of potent and selective PTP1B inhibitors occupying both the catalytic site and a portion of the noncatalytic, second phosphotyrosine binding site. Interestingly, oral biovailability has been observed in rats for some compounds. Furthermore, we demonstrated in vivo plasma glucose lowering effects with compound 12d in ob/ob mice.

  DOI：

  10.1021/jm0205696
• 作为产物：
  描述：

  2-氨基苯乙醇 、 二苯基碘酸 在 copper diacetate 作用下， 以 异丙醇 为溶剂， 反应 23.0h， 生成 2-[2-(2-羟基-乙基)-苯基氨基]-苯甲酸
  参考文献：
  名称：

  Discovery and Structure−Activity Relationship of Oxalylarylaminobenzoic Acids as Inhibitors of Protein Tyrosine Phosphatase 1B

  摘要：

  Protein Tyrosine phosphatase 1B (PTP1B) has been implicated as a key negative regulator of both insulin and leptin signaling pathways. Using an NMR-based screening approach with 15N- and 13C-labeled PTP1B, we have identified 2,3-dimethylphenyloxalylaminobenzoic acid (1) as a general, reversible, and competitive PTPase inhibitor. Structure-based approach guided by X-ray crystallography facilitated the development of 1 into a novel series of potent and selective PTP1B inhibitors occupying both the catalytic site and a portion of the noncatalytic, second phosphotyrosine binding site. Interestingly, oral biovailability has been observed in rats for some compounds. Furthermore, we demonstrated in vivo plasma glucose lowering effects with compound 12d in ob/ob mice.

  DOI：

  10.1021/jm0205696

文献信息

• Discovery and Structure−Activity Relationship of Oxalylarylaminobenzoic Acids as Inhibitors of Protein Tyrosine Phosphatase 1B
  作者：Gang Liu、Bruce G. Szczepankiewicz、Zhonghua Pei、David A. Janowick、Zhili Xin、Philip J. Hajduk、Cele Abad-Zapatero、Heng Liang、Charles W. Hutchins、Stephen W. Fesik、Steve J. Ballaron、Mike A. Stashko、Tom Lubben、Amanda K. Mika、Bradley A. Zinker、James M. Trevillyan、Michael R. Jirousek

  DOI：10.1021/jm0205696

  日期：2003.5.1

  Protein Tyrosine phosphatase 1B (PTP1B) has been implicated as a key negative regulator of both insulin and leptin signaling pathways. Using an NMR-based screening approach with 15N- and 13C-labeled PTP1B, we have identified 2,3-dimethylphenyloxalylaminobenzoic acid (1) as a general, reversible, and competitive PTPase inhibitor. Structure-based approach guided by X-ray crystallography facilitated the development of 1 into a novel series of potent and selective PTP1B inhibitors occupying both the catalytic site and a portion of the noncatalytic, second phosphotyrosine binding site. Interestingly, oral biovailability has been observed in rats for some compounds. Furthermore, we demonstrated in vivo plasma glucose lowering effects with compound 12d in ob/ob mice.