6-(benzyloxy)-3-(chloromethyl)-1-(methylsulfonyl)indoline | 152568-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-(benzyloxy)-3-(chloromethyl)-1-(methylsulfonyl)indoline
• 英文别名: 3-(Chloromethyl)-1-methylsulfonyl-6-phenylmethoxy-2,3-dihydroindole
• CAS: 152568-61-1
• 化学式: C₁₇H₁₈ClNO₃S
• 分子量: 351.854
• InChiKey: ZDHXDSIOQZSTPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(benzyloxy)-3-(chloromethyl)-1-(methylsulfonyl)indoline 在 palladium on activated charcoal 、 ammonium formate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 以94%的产率得到2-(Chloromethyl)-6-hydroxy-1-(methylsulphonyl)-indoline
  参考文献：
  名称：

  CC-1065 functional analogs possessing different electron-withdrawing substituents and leaving groups: synthesis, kinetics, and sequence specificity of reaction with DNA and biological evaluation

  摘要：

  Antitumor agent CC-1065 functional analogues possessing different electron-withdrawing substituents and leaving groups have been synthesized. The extent and the relative rates of DNA cleavage following alkylation by these CPI structures and thermal treatment were determined independently by an ethidium binding assay and by agarose gel electrophoresis experiments. The anticipated preferential covalent binding to adenine sites within the minor groove was confirmed by sequencing determination of selected agents on high-resolution gels. Certain of the synthetic agents, unlike CC-1065, also bind covalently to G sites with weaker intensity. The cytotoxicities of these compounds were also determined against KB cells in vitro. Compounds bearing a bromo or nitro group in the benzene ring and a methylsulfonyl as a leaving group are 10 and 5 times more potent than their unsubstituted counterparts, respectively. Compounds bearing a methylsulfonyl as a leaving group are more potent than those bearing a chlorine.

  DOI：

  10.1021/jm00078a005
• 作为产物：
  描述：

  6-(benzyloxy)-1-(methylsulfonyl)-3-<<(methylsulfonyl)oxy>methyl>indoline 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 以69%的产率得到6-(benzyloxy)-3-(chloromethyl)-1-(methylsulfonyl)indoline
  参考文献：
  名称：

  CC-1065 functional analogs possessing different electron-withdrawing substituents and leaving groups: synthesis, kinetics, and sequence specificity of reaction with DNA and biological evaluation

  摘要：

  Antitumor agent CC-1065 functional analogues possessing different electron-withdrawing substituents and leaving groups have been synthesized. The extent and the relative rates of DNA cleavage following alkylation by these CPI structures and thermal treatment were determined independently by an ethidium binding assay and by agarose gel electrophoresis experiments. The anticipated preferential covalent binding to adenine sites within the minor groove was confirmed by sequencing determination of selected agents on high-resolution gels. Certain of the synthetic agents, unlike CC-1065, also bind covalently to G sites with weaker intensity. The cytotoxicities of these compounds were also determined against KB cells in vitro. Compounds bearing a bromo or nitro group in the benzene ring and a methylsulfonyl as a leaving group are 10 and 5 times more potent than their unsubstituted counterparts, respectively. Compounds bearing a methylsulfonyl as a leaving group are more potent than those bearing a chlorine.

  DOI：

  10.1021/jm00078a005

文献信息

• CC-1065 functional analogs possessing different electron-withdrawing substituents and leaving groups: synthesis, kinetics, and sequence specificity of reaction with DNA and biological evaluation
  作者：Yuqiang Wang、Rajan Gupta、Liren Huang、J. William Lown

  DOI：10.1021/jm00078a005

  日期：1993.12

  Antitumor agent CC-1065 functional analogues possessing different electron-withdrawing substituents and leaving groups have been synthesized. The extent and the relative rates of DNA cleavage following alkylation by these CPI structures and thermal treatment were determined independently by an ethidium binding assay and by agarose gel electrophoresis experiments. The anticipated preferential covalent binding to adenine sites within the minor groove was confirmed by sequencing determination of selected agents on high-resolution gels. Certain of the synthetic agents, unlike CC-1065, also bind covalently to G sites with weaker intensity. The cytotoxicities of these compounds were also determined against KB cells in vitro. Compounds bearing a bromo or nitro group in the benzene ring and a methylsulfonyl as a leaving group are 10 and 5 times more potent than their unsubstituted counterparts, respectively. Compounds bearing a methylsulfonyl as a leaving group are more potent than those bearing a chlorine.