1-(4-Methylphenyl)sulfonyl-4-phenylpyrrole-2-carbaldehyde | 177949-82-5

• 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-4-phenylpyrrole-2-carbaldehyde
• CAS: 177949-82-5
• 化学式: C₁₈H₁₅NO₃S
• 分子量: 325.388
• InChiKey: POWYUQKPPPIGGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：

  5-ureidoindolin-2-one 、 1-(4-Methylphenyl)sulfonyl-4-phenylpyrrole-2-carbaldehyde 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 [(3Z)-2-oxo-3-[(4-phenyl-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-5-yl]urea
  参考文献：
  名称：

  Indolinone based phosphoinositide-dependent kinase-1 (PDK1) inhibitors. Part 2: Optimization of BX-517

  摘要：

  Based on the lead compound BX-517, a series of C-4 ' substituted indolinones have been synthesized and evaluated for PDK1 inhibition. Modification at C-4 ' of the pyrrole afforded potent compounds (7b and 7d) with improved solubility and ADME properties. In this letter, we describe the synthesis, selectivity profile, and pharmacokinetic data of selected compounds. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.060
• 作为产物：
  描述：

  4-溴-1H-吡咯-2-甲醛 在 四(三苯基膦)钯 sodium t-butanolate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 1-(4-Methylphenyl)sulfonyl-4-phenylpyrrole-2-carbaldehyde
  参考文献：
  名称：

  Indolinone based phosphoinositide-dependent kinase-1 (PDK1) inhibitors. Part 2: Optimization of BX-517

  摘要：

  Based on the lead compound BX-517, a series of C-4 ' substituted indolinones have been synthesized and evaluated for PDK1 inhibition. Modification at C-4 ' of the pyrrole afforded potent compounds (7b and 7d) with improved solubility and ADME properties. In this letter, we describe the synthesis, selectivity profile, and pharmacokinetic data of selected compounds. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.060

文献信息

• A general synthesis of β-aryl and heteroarylpyrroles by palladium-catalyzed coupling reaction of β-tributylstannylpyrrole with aryl and heteroaryl halides
  作者：Jianji Wang、A.Ian Scott

  DOI：10.1016/0040-4039(96)00530-8

  日期：1996.5

  Several β-aryl and heteroarylpyrroles have been synthesized by palladium-catalyzed coupling reaction of β-tributylstannylpyrroles with aryl and heteroaryl halides in 62–89% yields. These precursors may be readily converted into β-aryl and heteroaryl substituted porphyrins for the study of the oxophlorin to oxaporphyrin conversion in heme catabolism, catalyzed by heme oxygenase.

  通过钯催化的β-三丁基锡烷基吡咯与芳基卤化物和杂芳基卤化物的偶合反应，已经合成了几种β-芳基和杂芳基吡咯。这些前体可以容易地转化为β-芳基和杂芳基取代的卟啉，用于研究在血红素加氧酶催化下血红素分解代谢中的氧代卟啉向氧杂卟啉的转化。