4-(1'-benzenesulfonylindol-3'-yl)-2-(4'-chlorophenyl)oxazole | 1220958-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1'-benzenesulfonylindol-3'-yl)-2-(4'-chlorophenyl)oxazole
• 英文别名: 4-[1-(Benzenesulfonyl)indol-3-yl]-2-(4-chlorophenyl)-1,3-oxazole
• CAS: 1220958-40-6
• 化学式: C₂₃H₁₅ClN₂O₃S
• 分子量: 434.903
• InChiKey: KNCMCGXVLAKZFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(1'-benzenesulfonylindol-3'-yl)-2-(4'-chlorophenyl)oxazole 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以84%的产率得到2-(4'-chlorophenyl)-4-(3'-indolyl)-oxazole
  参考文献：
  名称：

  An expeditious synthesis and anticancer activity of novel 4-(3′-indolyl)oxazoles

  摘要：

  A series of 4-(3'-indolyl)oxazole congeners have been synthesized and studied for their cytotoxicity against six cancer cell lines. Reaction of 3-acetyl-1'-benzenesulfonylindole with [hydroxy(tosyloxy)iodo]benzene afforded pure 3-tosyloxyacetyl-1'-benzenesuifonylindole. Microwave-accelerated neat reaction of 3-tosyloxyacetyl-1-benzenesulfonylindole with amides resulted in the exclusive formation of 4-(1'-benzenesulfonylindol-3'-yl)-2-substituted oxazoles (4) in very good yield. Treatment of 4 with aqueous sodium hydroxide under refluxing conditions afforded pure 4-(3'-indolyl)-2-substituted oxazoles (5) in excellent yield. The 4-(T-indolyl)oxazoles; 5d and 11 were found to be most cytotoxic and selective against various cancer cell lines. Compounds 5g, 5j and 51 showed moderate anticancer activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.024
• 作为产物：
  描述：

  3-tosyloxyacetyl-1-benzenesulfonylindole 、 4-氯苯甲酰胺 以80%的产率得到4-(1'-benzenesulfonylindol-3'-yl)-2-(4'-chlorophenyl)oxazole
  参考文献：
  名称：

  An expeditious synthesis and anticancer activity of novel 4-(3′-indolyl)oxazoles

  摘要：

  A series of 4-(3'-indolyl)oxazole congeners have been synthesized and studied for their cytotoxicity against six cancer cell lines. Reaction of 3-acetyl-1'-benzenesulfonylindole with [hydroxy(tosyloxy)iodo]benzene afforded pure 3-tosyloxyacetyl-1'-benzenesuifonylindole. Microwave-accelerated neat reaction of 3-tosyloxyacetyl-1-benzenesulfonylindole with amides resulted in the exclusive formation of 4-(1'-benzenesulfonylindol-3'-yl)-2-substituted oxazoles (4) in very good yield. Treatment of 4 with aqueous sodium hydroxide under refluxing conditions afforded pure 4-(3'-indolyl)-2-substituted oxazoles (5) in excellent yield. The 4-(T-indolyl)oxazoles; 5d and 11 were found to be most cytotoxic and selective against various cancer cell lines. Compounds 5g, 5j and 51 showed moderate anticancer activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.024

文献信息

• An expeditious synthesis and anticancer activity of novel 4-(3′-indolyl)oxazoles
  作者：Dalip Kumar、N. Maruthi Kumar、Swapna Sundaree、Emmanuel O. Johnson、Kavita Shah

  DOI：10.1016/j.ejmech.2009.12.024

  日期：2010.3

  A series of 4-(3'-indolyl)oxazole congeners have been synthesized and studied for their cytotoxicity against six cancer cell lines. Reaction of 3-acetyl-1'-benzenesulfonylindole with [hydroxy(tosyloxy)iodo]benzene afforded pure 3-tosyloxyacetyl-1'-benzenesuifonylindole. Microwave-accelerated neat reaction of 3-tosyloxyacetyl-1-benzenesulfonylindole with amides resulted in the exclusive formation of 4-(1'-benzenesulfonylindol-3'-yl)-2-substituted oxazoles (4) in very good yield. Treatment of 4 with aqueous sodium hydroxide under refluxing conditions afforded pure 4-(3'-indolyl)-2-substituted oxazoles (5) in excellent yield. The 4-(T-indolyl)oxazoles; 5d and 11 were found to be most cytotoxic and selective against various cancer cell lines. Compounds 5g, 5j and 51 showed moderate anticancer activity. (C) 2010 Elsevier Masson SAS. All rights reserved.