3-[6-hydroxy-5-(2-hydroxyethyl)-2-morpholin-4-yl-pyrimidin-4-yl]-N-methyl-benzenesulfonamide | 1421621-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-[6-hydroxy-5-(2-hydroxyethyl)-2-morpholin-4-yl-pyrimidin-4-yl]-N-methyl-benzenesulfonamide
• CAS: 1421621-96-6
• 化学式: C₁₇H₂₂N₄O₅S
• 分子量: 394.451
• InChiKey: KKUPEBUWNVTPAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  124.88
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-[6-hydroxy-5-(2-hydroxyethyl)-2-morpholin-4-yl-pyrimidin-4-yl]-N-methyl-benzenesulfonamide 在 三氯氧磷 作用下， 反应 24.0h， 以14%的产率得到3-[6-chloro-5-(2-chloroethyl)-2-morpholin-4-yl-pyrimidin-4-yl]-N-methyl-benzenesulfonamide
  参考文献：
  名称：

  Lead optimization of a dihydropyrrolopyrimidine inhibitor against phosphoinositide 3-kinase (PI3K) to improve the phenol glucuronic acid conjugation

  摘要：

  Our lead compound for a phosphoinositide 3-kinase (PI3K) inhibitor (1) was metabolically unstable because of rapid glucuronidation of the phenol moiety. Based on structure-activity relationship (SAR) information and a FlexSIS docking simulation score, aminopyrimidine was identified as a bioisostere of phenol. An X-ray structure study revealed a hydrogen bonding pattern of aminopyrimidine derivatives. Finally, aminopyrimidine derivatives 33 showed strong tumor growth inhibition against a KPL-4 breast cancer xenograft model in vivo. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.112
• 作为产物：
  描述：

  4-<(N-methylamino)sulfonyl>benzoyl chloride 在 正丁基锂 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 2.25h， 生成 3-[6-hydroxy-5-(2-hydroxyethyl)-2-morpholin-4-yl-pyrimidin-4-yl]-N-methyl-benzenesulfonamide
  参考文献：
  名称：

  Lead optimization of a dihydropyrrolopyrimidine inhibitor against phosphoinositide 3-kinase (PI3K) to improve the phenol glucuronic acid conjugation

  摘要：

  Our lead compound for a phosphoinositide 3-kinase (PI3K) inhibitor (1) was metabolically unstable because of rapid glucuronidation of the phenol moiety. Based on structure-activity relationship (SAR) information and a FlexSIS docking simulation score, aminopyrimidine was identified as a bioisostere of phenol. An X-ray structure study revealed a hydrogen bonding pattern of aminopyrimidine derivatives. Finally, aminopyrimidine derivatives 33 showed strong tumor growth inhibition against a KPL-4 breast cancer xenograft model in vivo. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.112