2-(4-{[(3-Chloro-4-methoxyphenyl)methyl]amino}-6-[(dimethylsulfamoyl)amino]-7-methoxyquinazolin-8-yl)ethan-1-ol | 1349752-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(4-{[(3-Chloro-4-methoxyphenyl)methyl]amino}-6-[(dimethylsulfamoyl)amino]-7-methoxyquinazolin-8-yl)ethan-1-ol
• 英文别名: 4-[(3-chloro-4-methoxyphenyl)methylamino]-6-(dimethylsulfamoylamino)-8-(2-hydroxyethyl)-7-methoxyquinazoline
• CAS: 1349752-80-2
• 化学式: C₂₁H₂₆ClN₅O₅S
• 分子量: 495.987
• InChiKey: GCBJQSZJMUMFEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 2-(4-{[(3-Chloro-4-methoxyphenyl)methyl]amino}-6-[(dimethylsulfamoyl)amino]-7-methoxyquinazolin-8-yl)ethan-1-ol
  参考文献：
  名称：

  Discovery of potent, selective, and orally bioavailable PDE5 inhibitor: Methyl-4-(3-chloro-4-methoxybenzylamino)-8-(2-hydroxyethyl)-7-methoxyquinazolin-6-ylmethylcarbamate (CKD 533)

  摘要：

  In a continuing effort to discover novel PDE5 inhibitors, we have successfully found quinazolines with 4-benzylamino substitution as potent and selective PDE5 inhibitors. Initial lead compound (1) was found to be easily metabolized when incubated with human liver microsomes mainly through C6 amide hydrolysis. Blocking of this metabolic hot spot led to discovery of 10 (CKD533) which is highly potent, selective and orally efficacious in conscious rabbit model for erectile dysfunction and now is undergoing preclinical toxicology study. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.071