2-(Chloromethyl)-6-hydroxy-1-(methylsulphonyl)-indoline | 152568-62-2

• 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: 2-(Chloromethyl)-6-hydroxy-1-(methylsulphonyl)-indoline
• 英文别名: 3-(chloromethyl)-1-methylsulfonyl-2,3-dihydroindol-6-ol
• CAS: 152568-62-2
• 化学式: C₁₀H₁₂ClNO₃S
• 分子量: 261.729
• InChiKey: NKRUFEUYGKNSDG-UHFFFAOYSA-N

物化性质

• 沸点：
  441.8±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Chloromethyl)-6-hydroxy-1-(methylsulphonyl)-indoline 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以61%的产率得到5-bromo-3-(chloromethyl)-6-hydroxy-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
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 platinum(IV) oxide 、 palladium on activated charcoal 吡啶 、 甲酸 、 氯化亚砜 、 sodium azide 、 硫酸 、 氢气 、 甲酸铵 、 sodium hydride 、 二异丁基氢化铝 、 N,N-二甲基甲酰胺 、 尿素 、 lithium chloride 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， -8.0~90.0 ℃ 、344.73 kPa 条件下， 反应 48.74h， 生成 2-(Chloromethyl)-6-hydroxy-1-(methylsulphonyl)-indoline
  参考文献：
  名称：

  Tercel, Moana; Denny, William A., Journal of the Chemical Society. Perkin transactions I, 1998, # 3, p. 509 - 519

  摘要：

  DOI：

文献信息

• Nitrogen and sulfur analogues of the secoCI alkylating agent: Synthesis and cytotoxicity
  作者：M. Tercel、W.A. Denny、W.R. Wilson

  DOI：10.1016/s0960-894x(96)00507-0

  日期：1996.11

  The first synthesis of seca-CI alkylating agents bearing a nitrogen or sulfur substituent in place of the oxygen at C-6 is described. In comparison with a phenol, an amino substituent confers reduced but significant cytotoxicity, even when mono- or dimethylated, while sulfur analogues are considerably less potent. Copyright (C) 1996 Elsevier Science Ltd
• Tercel, Moana; Denny, William A., Journal of the Chemical Society. Perkin transactions I, 1998, # 3, p. 509 - 519
  作者：Tercel, Moana、Denny, William A.

  DOI：——

  日期：——
• 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.