(4-Methoxyphenyl)methyl 2-cyano-3-(phenoxycarbonylamino)-3-sulfanylidenepropanimidothioate | 900525-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4-Methoxyphenyl)methyl 2-cyano-3-(phenoxycarbonylamino)-3-sulfanylidenepropanimidothioate
• 英文别名: (4-methoxyphenyl)methyl 2-cyano-3-(phenoxycarbonylamino)-3-sulfanylidenepropanimidothioate
• CAS: 900525-08-8
• 化学式: C₁₉H₁₇N₃O₃S₂
• 分子量: 399.494
• InChiKey: UERYGLGVMTWHSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4-Methoxyphenyl)methyl 2-cyano-3-(phenoxycarbonylamino)-3-sulfanylidenepropanimidothioate 在 吡啶 、 硫化氢 、 mercury(II) diacetate 、 碘 、 三氟乙酸 作用下， 生成 (4-cyano-3-mercapto-isothiazol-5-yl)-carbamic acid phenyl ester
  参考文献：
  名称：

  Discovery of novel isothiazole inhibitors of the TrkA kinase: Structure–activity relationship, computer modeling, optimization, and identification of highly potent antagonists

  摘要：

  The design, synthesis, and biological evaluation of potent inhibitors of the TrkA kinase is presented. A homology model is created to aid in the enhancement of potency and selectivity of isothiazole inhibitors found during a high-throughput screen. Three different syntheses are utilized to make diverse analogs within this series. Aminoheterocycles are found to be good urea surrogates, whereas bicyclic substituents on the C3 thio group were found to be extremely potent TrkA inhibitors in kinase and cell assays. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.003
• 作为产物：
  描述：

  4-甲氧基苄硫醇 生成 (4-Methoxyphenyl)methyl 2-cyano-3-(phenoxycarbonylamino)-3-sulfanylidenepropanimidothioate
  参考文献：
  名称：

  Discovery of novel isothiazole inhibitors of the TrkA kinase: Structure–activity relationship, computer modeling, optimization, and identification of highly potent antagonists

  摘要：

  The design, synthesis, and biological evaluation of potent inhibitors of the TrkA kinase is presented. A homology model is created to aid in the enhancement of potency and selectivity of isothiazole inhibitors found during a high-throughput screen. Three different syntheses are utilized to make diverse analogs within this series. Aminoheterocycles are found to be good urea surrogates, whereas bicyclic substituents on the C3 thio group were found to be extremely potent TrkA inhibitors in kinase and cell assays. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.003

文献信息

• Discovery of novel isothiazole inhibitors of the TrkA kinase: Structure–activity relationship, computer modeling, optimization, and identification of highly potent antagonists
  作者：Blaise Lippa、Joel Morris、Matthew Corbett、Tricia A. Kwan、Mark C. Noe、Sheri L. Snow、Thomas G. Gant、Melchiorra Mangiaracina、Heather A. Coffey、Barbara Foster、Elisabeth A. Knauth、Matthew D. Wessel

  DOI：10.1016/j.bmcl.2006.04.003

  日期：2006.7

  The design, synthesis, and biological evaluation of potent inhibitors of the TrkA kinase is presented. A homology model is created to aid in the enhancement of potency and selectivity of isothiazole inhibitors found during a high-throughput screen. Three different syntheses are utilized to make diverse analogs within this series. Aminoheterocycles are found to be good urea surrogates, whereas bicyclic substituents on the C3 thio group were found to be extremely potent TrkA inhibitors in kinase and cell assays. (c) 2006 Elsevier Ltd. All rights reserved.