N-methyl-3-(2-oxo-tetrahydro-furan-3-carbonyl)-benzenesulfonamide | 1421621-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methyl-3-(2-oxo-tetrahydro-furan-3-carbonyl)-benzenesulfonamide
• 英文别名: N-methyl-3-(2-oxooxolane-3-carbonyl)benzenesulfonamide
• CAS: 1421621-95-5
• 化学式: C₁₂H₁₃NO₅S
• 分子量: 283.305
• InChiKey: UYOPNYNRZFKRCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-methyl-3-(2-oxo-tetrahydro-furan-3-carbonyl)-benzenesulfonamide 在 sodium methylate 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 26.0h， 生成 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：

  3-[(甲氨基)磺酰基]苯甲酸 在 正丁基锂 、 氯化亚砜 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.25h， 生成 N-methyl-3-(2-oxo-tetrahydro-furan-3-carbonyl)-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

文献信息

• Lead optimization of a dihydropyrrolopyrimidine inhibitor against phosphoinositide 3-kinase (PI3K) to improve the phenol glucuronic acid conjugation
  作者：Hatsuo Kawada、Hirosato Ebiike、Masao Tsukazaki、Mitsuaki Nakamura、Kenji Morikami、Kiyoshi Yoshinari、Miyuki Yoshida、Kotaro Ogawa、Nobuo Shimma、Takuo Tsukuda、Jun Ohwada

  DOI：10.1016/j.bmcl.2012.11.112

  日期：2013.2

  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.