[4-(4-Chloro-phenyl)-1H-pyrrol-3-yl]-(5-chloro-thiophen-2-yl)-methanone | 286956-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [4-(4-Chloro-phenyl)-1H-pyrrol-3-yl]-(5-chloro-thiophen-2-yl)-methanone
• 英文别名: [4-(4-chlorophenyl)-1H-pyrrol-3-yl]-(5-chlorothiophen-2-yl)methanone
• CAS: 286956-31-8
• 化学式: C₁₅H₉Cl₂NOS
• 分子量: 322.215
• InChiKey: KFTUNPFGQWMLTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘乙烷 、 [4-(4-Chloro-phenyl)-1H-pyrrol-3-yl]-(5-chloro-thiophen-2-yl)-methanone 在 四丁基硫酸氢铵 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以96%的产率得到[4-(4-Chloro-phenyl)-1-ethyl-1H-pyrrol-3-yl]-(5-chloro-thiophen-2-yl)-methanone
  参考文献：
  名称：

  The pyrrole moiety as a template for COX-1/COX-2 inhibitors

  摘要：

  Aroyl- and thiophene-substituted pyrrole derivatives have been synthesized as a new class of COX-1/COX-2 inhibitors. The inhibition of COX-1 was evaluated in a biological system using bovine PMNLs as the enzyme source, whereas LPS-stimulated human monocytes served as the enzyme source for inducible COX-2. The determination of the concentration of arachidonic acid metabolites was performed by HPLC for COX-1 and RIA for COX-2. Variation of the substitution pattern led to a series of active compounds which showed inhibition for COX-1 and COX-2. Structural requirements for the development of COX-1/COX-2 inhibitors are discussed, (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00150-1
• 作为产物：
  描述：

  2-乙酰基-5-氯噻酚 在 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.25h， 生成 [4-(4-Chloro-phenyl)-1H-pyrrol-3-yl]-(5-chloro-thiophen-2-yl)-methanone
  参考文献：
  名称：

  The pyrrole moiety as a template for COX-1/COX-2 inhibitors

  摘要：

  Aroyl- and thiophene-substituted pyrrole derivatives have been synthesized as a new class of COX-1/COX-2 inhibitors. The inhibition of COX-1 was evaluated in a biological system using bovine PMNLs as the enzyme source, whereas LPS-stimulated human monocytes served as the enzyme source for inducible COX-2. The determination of the concentration of arachidonic acid metabolites was performed by HPLC for COX-1 and RIA for COX-2. Variation of the substitution pattern led to a series of active compounds which showed inhibition for COX-1 and COX-2. Structural requirements for the development of COX-1/COX-2 inhibitors are discussed, (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00150-1

文献信息

• The pyrrole moiety as a template for COX-1/COX-2 inhibitors
  作者：Gerd Dannhardt、Werner Kiefer、Godehard Krämer、Sabine Maehrlein、Ulrike Nowe、Bernd Fiebich

  DOI：10.1016/s0223-5234(00)00150-1

  日期：2000.5

  Aroyl- and thiophene-substituted pyrrole derivatives have been synthesized as a new class of COX-1/COX-2 inhibitors. The inhibition of COX-1 was evaluated in a biological system using bovine PMNLs as the enzyme source, whereas LPS-stimulated human monocytes served as the enzyme source for inducible COX-2. The determination of the concentration of arachidonic acid metabolites was performed by HPLC for COX-1 and RIA for COX-2. Variation of the substitution pattern led to a series of active compounds which showed inhibition for COX-1 and COX-2. Structural requirements for the development of COX-1/COX-2 inhibitors are discussed, (C) 2000 Editions scientifiques et medicales Elsevier SAS.