[5-[[4-(乙酰基氨基)苯基]硫代]-1H-苯并咪唑-2-基]-氨基甲酸甲酯 | 56073-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: [5-[[4-(乙酰基氨基)苯基]硫代]-1H-苯并咪唑-2-基]-氨基甲酸甲酯
• 英文名称: [5-(4-acetylamino-phenylsulfanyl)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester
• 英文别名: methyl N-[6-(4-acetamidophenyl)sulfanyl-1H-benzimidazol-2-yl]carbamate
• CAS: 56073-95-1
• 化学式: C₁₇H₁₆N₄O₃S
• 分子量: 356.405
• InChiKey: SUZMAVYKEQSUQK-UHFFFAOYSA-N

物化性质

• 熔点：
  280 °C
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  [5-[[4-(乙酰基氨基)苯基]硫代]-1H-苯并咪唑-2-基]-氨基甲酸甲酯 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：

  Benzimidazole vascular damaging agents

  摘要：

  提供了由取代的5（6）-取代苯并咪唑-2-氨基甲酸酯组成的血管破坏剂。这些剂对于制备治疗涉及新血管生成的疾病的药物特别有用，尤其是用于实体肿瘤、黄斑变性、糖尿病视网膜病变、类风湿性关节炎、银屑病和动脉粥样硬化的治疗。实施例包括式I的5（6）-取代苯并咪唑-2-氨基甲酸酯，其中A代表多取代的烷基或芳香环。

  公开号：

  US07081469B2
• 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 [5-[[4-(乙酰基氨基)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

文献信息

• Benzimidazole vascular damaging agents
  申请人：Angiogene Pharmaceuticals Ltd.

  公开号：US07081469B2

  公开（公告）日：2006-07-25

  Vascular damaging agents composed of substituted 5(6)-substituted benzimidazole-2-carbamates are provided. These agents are useful in the preparation of medicaments for the treatment of diseases involving neovascularisation, particularly for the treatment of solid tumors, macular degeneration, diabetic retinopathy, rheumatoid arthritis, psoriasis, and atherosclerosis. Embodiments include a 5(6)-substituted benzimidazole-2-carbamate of formula I wherein A represents a multi-substituted alkyl group or aromatic ring.

  提供了由取代的5（6）-取代苯并咪唑-2-氨基甲酸酯组成的血管破坏剂。这些剂对于制备治疗涉及新血管生成的疾病的药物特别有用，尤其是用于实体肿瘤、黄斑变性、糖尿病视网膜病变、类风湿性关节炎、银屑病和动脉粥样硬化的治疗。实施例包括式I的5（6）-取代苯并咪唑-2-氨基甲酸酯，其中A代表多取代的烷基或芳香环。
• 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：——
• WO2006/76376
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors
  作者：Masaichi Hasegawa、Naohiko Nishigaki、Yoshiaki Washio、Kazuya Kano、Philip A. Harris、Hideyuki Sato、Ichiro Mori、Rob I. West、Megumi Shibahara、Hiroko Toyoda、Liping Wang、Robert T. Nolte、James M. Veal、Mui Cheung

  DOI：10.1021/jm0611051

  日期：2007.9.1

  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.