4-(2-(1H-benzo[d]imidazol-2-ylthio) acetamido)benzoic acid | 86109-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-(1H-benzo[d]imidazol-2-ylthio) acetamido)benzoic acid
• 英文别名: 4-{[(1H-benzimidazol-2-ylsulfanyl)acetyl]amino}benzoic acid；4-[[2-(1H-benzimidazol-2-ylsulfanyl)acetyl]amino]benzoic acid
• CAS: 86109-64-0
• 化学式: C₁₆H₁₃N₃O₃S
• 分子量: 327.364
• InChiKey: YEIYHUXGPBAPFP-UHFFFAOYSA-N

物化性质

• 熔点：
  270-271 °C(Solv: ethanol (64-17-5))
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-(1H-benzo[d]imidazol-2-ylthio) acetamido)benzoic acid 在 吡啶 、 乙酸酐 作用下， 反应 2.0h， 以80%的产率得到
  参考文献：
  名称：

  El Sherief; Mahmoud; Abdel Rahman, Journal of the Indian Chemical Society, 1983, vol. 60, # 1, p. 58 - 60

  摘要：

  DOI：
• 作为产物：
  描述：

  对氨基苯甲酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 生成 4-(2-(1H-benzo[d]imidazol-2-ylthio) acetamido)benzoic acid
  参考文献：
  名称：

  Molecular modeling and synthesis of ZINC02765569 derivatives as protein tyrosine phosphatase 1B inhibitors: lead optimization study

  摘要：

  This article describes design, synthesis, and molecular modeling studies of the ZINC02765569 derivatives as potent protein tyrosine phosphatase 1B (PTP1B) inhibitors, which was previously reported as a vHTS hit (ZINC02765569) by our laboratory. Ten compounds were synthesized and characterized by IR, MASS, and NMR followed by in vitro screening for PTP1B inhibition and glucose uptake in skeletal muscle L6 myotubes. The most potent compound 3j shows 66.4 % in vitro PTP1B inhibition and 39.6 % increase in glucose uptake. Glide was used to study the nature of interactions governing binding of designed molecules with active site of the PTP1B enzyme.

  DOI：

  10.1007/s00044-012-0165-0

文献信息

• EL-SHERIEF, H. A.;MAHMOUD, A. M.;ABDEL-RAHMAN, A. E.;EL-NAGGAR, G. M., J. INDIAN CHEM. SOC., 1983, 60, N 1, 58-60
  作者：EL-SHERIEF, H. A.、MAHMOUD, A. M.、ABDEL-RAHMAN, A. E.、EL-NAGGAR, G. M.

  DOI：——

  日期：——
• Molecular modeling and synthesis of ZINC02765569 derivatives as protein tyrosine phosphatase 1B inhibitors: lead optimization study
  作者：Prashant Joshi、Girdhar Singh Deora、Vandana Rathore、Arun K. Rawat、A. K. Srivastava、Deepti Jain

  DOI：10.1007/s00044-012-0165-0

  日期：2013.4

  This article describes design, synthesis, and molecular modeling studies of the ZINC02765569 derivatives as potent protein tyrosine phosphatase 1B (PTP1B) inhibitors, which was previously reported as a vHTS hit (ZINC02765569) by our laboratory. Ten compounds were synthesized and characterized by IR, MASS, and NMR followed by in vitro screening for PTP1B inhibition and glucose uptake in skeletal muscle L6 myotubes. The most potent compound 3j shows 66.4 % in vitro PTP1B inhibition and 39.6 % increase in glucose uptake. Glide was used to study the nature of interactions governing binding of designed molecules with active site of the PTP1B enzyme.
• El Sherief; Mahmoud; Abdel Rahman, Journal of the Indian Chemical Society, 1983, vol. 60, # 1, p. 58 - 60
  作者：El Sherief、Mahmoud、Abdel Rahman、El Naggar

  DOI：——

  日期：——