N-{1-[3-fluoro-4-(methylsulfonylamino)phenyl]ethyl}-3-(4-tert-butylphenyl)-2-propenamide | 824937-17-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-{1-[3-fluoro-4-(methylsulfonylamino)phenyl]ethyl}-3-(4-tert-butylphenyl)-2-propenamide
• 英文别名: 3-(4-tert-butylphenyl)-N-[1-[3-fluoro-4-(methanesulfonamido)phenyl]ethyl]prop-2-enamide
• CAS: 824937-17-9
• 化学式: C₂₂H₂₇FN₂O₃S
• 分子量: 418.532
• InChiKey: MGIAWEQCVGZBOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-[3-fluoro-4-(methylsulfonylamino)phenyl]ethylamine 、 3-[4-叔丁基苯基]-2-丙烯酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以67%的产率得到N-{1-[3-fluoro-4-(methylsulfonylamino)phenyl]ethyl}-3-(4-tert-butylphenyl)-2-propenamide
  参考文献：
  名称：

  2-(4-Methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure–activity relationships in the B and C-regions

  摘要：

  On the basis of the previous lead N-4-t-butylbenzyl 2-(3-fluoro-4-methylsulfonylaminophenyl) propanamide (3) as a potent TRPV1 antagonist, structure-activity relationships for the B (propanamide part) and C-region (4-t-butylbenzyl part) have been investigated for rTRPV1 in CHO cells. The B-region was modified with dimethyl, cyclopropyl and reverse amides and then the C-region was replaced with 4-substituted phenyl, aryl alkyl and diaryl alkyl derivatives. Among them, compound 50 showed high binding affinity with K-i = 21.5 nM, which was twofold more potent than 3 and compound 54 exhibited potent antagonism with K-i(ant) = 8.0 nM comparable to 3. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.014