3-(4'-nitrophenyl)propyl methanesulfonate | 99676-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4'-nitrophenyl)propyl methanesulfonate
• 英文别名: 3-(p-nitrophenyl)propyl methanesulphonate；3-(4-Nitrophenyl)propyl methanesulfonate
• CAS: 99676-62-7
• 化学式: C₁₀H₁₃NO₅S
• 分子量: 259.283
• InChiKey: HJYSRVXZZZLJMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4'-nitrophenyl)propyl methanesulfonate 在 双氧水 、 sodium methylate 、 sodium acetate 、 铁粉 、 溶剂黄146 作用下， 以 甲醇 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 5.75h， 生成 1-acetoxy-3-(p-phthalimidophenyl)propyl p-tolyl sulphide
  参考文献：
  名称：

  Lucey, Neil M.; McElhinney, R. Stenley, Journal of Chemical Research, Miniprint, 1985, # 8, p. 2713 - 2723

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(4-硝基苯基)丙酸 在 吡啶 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-(4'-nitrophenyl)propyl methanesulfonate
  参考文献：
  名称：

  DNA-directed alkylating agents. 2. Synthesis and biological activity of platinum complexes linked to 9-anilinoacridine

  摘要：

  Two different classes of cis-diaminedichloroplatinum(II) complexes linked to the DNA-intercalating chromophore 9-anilinoacridine have been synthesized and evaluated as DNA-targeted antitumor agents. Two different Pt chelating ligands were investigated (based on 1,2-ethanediamine and 1,3-propanediamine), designed to deliver the Pt in an orientation likely to respectively enhance either intrastrand or interstrand cross-linking. Although both sets of ligands were somewhat unstable under neutral or basic conditions with respect to disproportionation, the corresponding Pt complexes, once prepared, appeared to be quite stable. All the Pt complexes were monitored for purity by TLC, HPLC, and FAB mass spectra, and the mode of Pt coordination was established by 195Pt NMR spectroscopy. The complexes appeared to cause simultaneous platination and intercalative unwinding of plasmid DNA. In vitro studies were carried out with both wild-type and cisplatin-resistant P388 cell lines. Whereas cisplatin itself and the ethylenediamine and 1,3-propanediamine complexes used as standards were about 10-fold less active against the resistant line, the ethylenediamine-linked Pt complexes showed no differential toxicity between the two lines and the propanediamine-linked complexes showed significant differentials (up to 8-fold) in favor of the cisplatin-resistant line. However, these were no greater than those shown by the unplatinated ligands themselves. The majority of the acridine complexes were inactive in vivo against the wild-type P388 leukemia. They were very insoluble, and although a suitable formulation was found, this may have been a factor. It is also possible that these compounds bind in such a way as to direct the Pt away from the major groove.

  DOI：

  10.1021/jm00173a015

文献信息

• Lucey, Neil M.; McElhinney, R. Stenley, Journal of Chemical Research, Miniprint, 1985, # 8, p. 2713 - 2723
  作者：Lucey, Neil M.、McElhinney, R. Stenley

  DOI：——

  日期：——
• DNA-directed alkylating agents. 2. Synthesis and biological activity of platinum complexes linked to 9-anilinoacridine
  作者：Brian D. Palmer、Ho H. Lee、Paul Johnson、Bruce C. Baguley、Geoffrey Wickham、Laurence P. G. Wakelin、W. David McFadyen、William A. Denny

  DOI：10.1021/jm00173a015

  日期：1990.11

  Two different classes of cis-diaminedichloroplatinum(II) complexes linked to the DNA-intercalating chromophore 9-anilinoacridine have been synthesized and evaluated as DNA-targeted antitumor agents. Two different Pt chelating ligands were investigated (based on 1,2-ethanediamine and 1,3-propanediamine), designed to deliver the Pt in an orientation likely to respectively enhance either intrastrand or interstrand cross-linking. Although both sets of ligands were somewhat unstable under neutral or basic conditions with respect to disproportionation, the corresponding Pt complexes, once prepared, appeared to be quite stable. All the Pt complexes were monitored for purity by TLC, HPLC, and FAB mass spectra, and the mode of Pt coordination was established by 195Pt NMR spectroscopy. The complexes appeared to cause simultaneous platination and intercalative unwinding of plasmid DNA. In vitro studies were carried out with both wild-type and cisplatin-resistant P388 cell lines. Whereas cisplatin itself and the ethylenediamine and 1,3-propanediamine complexes used as standards were about 10-fold less active against the resistant line, the ethylenediamine-linked Pt complexes showed no differential toxicity between the two lines and the propanediamine-linked complexes showed significant differentials (up to 8-fold) in favor of the cisplatin-resistant line. However, these were no greater than those shown by the unplatinated ligands themselves. The majority of the acridine complexes were inactive in vivo against the wild-type P388 leukemia. They were very insoluble, and although a suitable formulation was found, this may have been a factor. It is also possible that these compounds bind in such a way as to direct the Pt away from the major groove.