tert-butyl ({1-[(3-methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate | 1374671-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tert-butyl ({1-[(3-methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate
• 英文别名: tert-butyl N-[[1-(3-methoxyphenyl)sulfonyl-5-phenylpyrrol-3-yl]methyl]-N-methylcarbamate
• CAS: 1374671-88-1
• 化学式: C₂₄H₂₈N₂O₅S
• 分子量: 456.563
• InChiKey: JDCIZPOCWFYKIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl ({1-[(3-methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate 在 盐酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 以68%的产率得到1-{1-[(3-methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}-N-methylmethanamine hydrochloride
  参考文献：
  名称：

  Discovery of a Novel Pyrrole Derivative 1-[5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate (TAK-438) as a Potassium-Competitive Acid Blocker (P-CAB)

  摘要：

  In our pursuit of developing a novel and potent potassium-competitive acid blocker (P-CAB), we synthesized pyrrole derivatives focusing on compounds with low log D and high ligand-lipophilicity efficiency (LLE) values. Among the compounds synthesized, the compound 13e exhibited potent H+,K(+)ATPase inhibitory activity and potent gastric acid secretion inhibitory action in vivo. Its maximum efficacy was more potent and its duration of action was much longer than those of proton pump inhibitors (PPIs). Therefore, compound 13e (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine fumarate, TAK-438) was selected as a drug candidate for the treatment of gastroesophageal reflux disease (GERD), peptic ulcer, and other acid-related diseases.

  DOI：

  10.1021/jm300318t
• 作为产物：
  描述：

  沃诺拉赞杂质07 在 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 2.67h， 生成 tert-butyl ({1-[(3-methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate
  参考文献：
  名称：

  Discovery of a Novel Pyrrole Derivative 1-[5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate (TAK-438) as a Potassium-Competitive Acid Blocker (P-CAB)

  摘要：

  In our pursuit of developing a novel and potent potassium-competitive acid blocker (P-CAB), we synthesized pyrrole derivatives focusing on compounds with low log D and high ligand-lipophilicity efficiency (LLE) values. Among the compounds synthesized, the compound 13e exhibited potent H+,K(+)ATPase inhibitory activity and potent gastric acid secretion inhibitory action in vivo. Its maximum efficacy was more potent and its duration of action was much longer than those of proton pump inhibitors (PPIs). Therefore, compound 13e (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine fumarate, TAK-438) was selected as a drug candidate for the treatment of gastroesophageal reflux disease (GERD), peptic ulcer, and other acid-related diseases.

  DOI：

  10.1021/jm300318t

文献信息

• Discovery of a Novel Pyrrole Derivative 1-[5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1<i>H</i>-pyrrol-3-yl]-<i>N</i>-methylmethanamine Fumarate (TAK-438) as a Potassium-Competitive Acid Blocker (P-CAB)
  作者：Yasuyoshi Arikawa、Haruyuki Nishida、Osamu Kurasawa、Atsushi Hasuoka、Keizo Hirase、Nobuhiro Inatomi、Yasunobu Hori、Jun Matsukawa、Akio Imanishi、Mitsuyo Kondo、Naoki Tarui、Teruki Hamada、Terufumi Takagi、Toshiyuki Takeuchi、Masahiro Kajino

  DOI：10.1021/jm300318t

  日期：2012.5.10

  In our pursuit of developing a novel and potent potassium-competitive acid blocker (P-CAB), we synthesized pyrrole derivatives focusing on compounds with low log D and high ligand-lipophilicity efficiency (LLE) values. Among the compounds synthesized, the compound 13e exhibited potent H+,K(+)ATPase inhibitory activity and potent gastric acid secretion inhibitory action in vivo. Its maximum efficacy was more potent and its duration of action was much longer than those of proton pump inhibitors (PPIs). Therefore, compound 13e (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine fumarate, TAK-438) was selected as a drug candidate for the treatment of gastroesophageal reflux disease (GERD), peptic ulcer, and other acid-related diseases.