4-(4-acetamidophenylthio)-o-phenylenediamine | 56073-94-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(4-acetamidophenylthio)-o-phenylenediamine
• 英文别名: N-[4-(3,4-diaminophenylsulfanyl)phenyl]acetamide；N-(4-((3,4-diaminophenyl)thio)phenyl)acetamide；N-[4-(3,4-diaminophenyl)sulfanylphenyl]acetamide
• CAS: 56073-94-0
• 化学式: C₁₄H₁₅N₃OS
• 分子量: 273.359
• InChiKey: LVHALRPVBKOQHO-UHFFFAOYSA-N

物化性质

• 沸点：
  605.1±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-acetamidophenylthio)-o-phenylenediamine 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-[6-[(4-氨基苯基)硫代]-1H-苯并咪唑-2-基]-氨基甲酸甲酯
  参考文献：
  名称：

  Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors

  摘要：

  We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the NI nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the NI nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

  DOI：

  10.1021/jm0611051
• 作为产物：
  描述：

  4-乙酰氨基苯硫酚 在 sodium dithionite 、 potassium tert-butylate 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 6.0h， 生成 4-(4-acetamidophenylthio)-o-phenylenediamine
  参考文献：
  名称：

  Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors

  摘要：

  We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the NI nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the NI nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

  DOI：

  10.1021/jm0611051

文献信息

• Abuzar, Syed; Rao, K. V. B.; Sharma, Satyavan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 178 - 181
  作者：Abuzar, Syed、Rao, K. V. B.、Sharma, Satyavan、Gupta, Suman、Katiyar, J. C.

  DOI：——

  日期：——
• ABUZAR, SYED;RAO, K. V. B.;SHARMA, SATYAVAN;GUPTA, SUMAN;KATIYAR, J. C., INDIAN J. CHEM., 1985, 24, N 2, 178-181
  作者：ABUZAR, SYED、RAO, K. V. B.、SHARMA, SATYAVAN、GUPTA, SUMAN、KATIYAR, J. C.

  DOI：——

  日期：——