1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde | 881673-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde
• 英文别名: 1-[(4-Methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde；1-(4-methylphenyl)sulfonyl-5-phenylpyrrole-3-carbaldehyde
• CAS: 881673-31-0
• 化学式: C₁₈H₁₅NO₃S
• 分子量: 325.388
• InChiKey: NSLXRXVEXGLLNX-UHFFFAOYSA-N

物化性质

• 沸点：
  550.0±60.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.25h， 生成 N-methyl-1-{1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methanamine hydrochloride
  参考文献：
  名称：

  Discovery, synthesis, and biological evaluation of novel pyrrole derivatives as highly selective potassium-competitive acid blockers

  摘要：

  To discover a gastric antisecretory agent more potent than existing proton pump inhibitors, novel pyrrole derivatives were synthesized, and their H+, K+-ATPase inhibitory activities and inhibitory action on histamine-stimulated gastric acid secretion in rats were evaluated. Among the compounds synthesized, compound 17a exhibited selective and potent H+, K+-ATPase inhibitory activity through reversible and K+-competitive ionic binding; furthermore, compound 17c exhibited potent inhibitory action on histamine-stimulated gastric acid secretion in rats and Heidenhain pouch dogs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.014
• 作为产物：
  描述：

  ethyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carboxylate 在 四丙基高钌酸铵 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 2.5h， 生成 1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde
  参考文献：
  名称：

  Discovery, synthesis, and biological evaluation of novel pyrrole derivatives as highly selective potassium-competitive acid blockers

  摘要：

  To discover a gastric antisecretory agent more potent than existing proton pump inhibitors, novel pyrrole derivatives were synthesized, and their H+, K+-ATPase inhibitory activities and inhibitory action on histamine-stimulated gastric acid secretion in rats were evaluated. Among the compounds synthesized, compound 17a exhibited selective and potent H+, K+-ATPase inhibitory activity through reversible and K+-competitive ionic binding; furthermore, compound 17c exhibited potent inhibitory action on histamine-stimulated gastric acid secretion in rats and Heidenhain pouch dogs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.014

文献信息

• [EN] PROTON PUMP INHIBITORS<br/>[FR] INHIBITEURS DE POMPE A PROTONS
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2006036024A1

  公开（公告）日：2006-04-06

  Proton pump inhibitors which have excellent proton pumping activity and which can be converted in vivo into proton pump inhibitors to exhibit antiulcer effect and so on, containing compounds represented by the general formula (I) or salts thereof or prodrugs of the same: (I) wherein X and Y are each independently a free valency or a spacer whose main chain has 1 to 20 carbon atoms; R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; R2, R3 and R4 are each independently hydrogen, an optionally substituted hydrocarbon group, optionally substituted thienyl, optionally substituted benzo[b]thienyl, optionally substituted furyl, optionally substituted pyridyl, optionally substituted pyrazolyl, optionally substituted pyrimidinyl, acyl, halogeno, cyano, or nitro; and R5 and R6 are each independently hydrogen or an optionally substituted hydrocarbon group.

  质子泵抑制剂具有优异的质子泵活性，可以在体内转化为质子泵抑制剂，表现出抗溃疡作用等，包含由通式（I）表示的化合物或其盐或类似物：（I）其中X和Y分别是自由价或其主链具有1至20个碳原子的间隔物；R1是可选择地取代的碳氢基团或可选择地取代的杂环基团；R2、R3和R4分别是氢、可选择地取代的碳氢基团、可选择地取代的噻吩基、可选择地取代的苯并[b]噻吩基、可选择地取代的呋喃基、可选择地取代的吡啶基、可选择地取代的吡唑基、可选择地取代的嘧啶基、酰基、卤素、氰基或硝基；R5和R6分别是氢或可选择地取代的碳氢基团。
• Proton Pump Inhibitors
  申请人：Kajino Masahiro

  公开号：US20080139639A1

  公开（公告）日：2008-06-12

  A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R 1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R 5 and R 6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

  提供一种质子泵抑制剂，其中包含公式（I）所代表的化合物，其中X和Y相同或不同，每个都是具有1到20个碳原子的主链中的键或间隔物，R1是可选取代的碳氢化合物基团或可选取代的杂环基团，R2、R3和R4相同或不同，每个都是氢原子、可选取代的碳氢化合物基团、可选取代的噻吩基团、可选取代的苯并[b]噻吩基团、可选取代的呋喃基团、可选取代的吡啶基团、可选取代的吡唑基团、可选取代的嘧啶基团、酰基、卤素原子、氰基或硝基，R5和R6相同或不同，每个都是氢原子或可选取代的碳氢化合物基团。该化合物在体内转化为质子泵抑制剂后具有卓越的质子泵作用，并显示抗溃疡活性等，或其盐或前药。
• PROTON PUMP INHIBITORS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1803709B1

  公开（公告）日：2013-01-02
• Proton pump inhibitors
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2336107B1

  公开（公告）日：2015-09-23
• US20140343070A1
  申请人：——

  公开号：——

  公开（公告）日：——