1-(toluene-4-sulfonyloxy)-xanthen-9-one | 723250-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-(toluene-4-sulfonyloxy)-xanthen-9-one
• 英文别名: 1-(Toluol-4-sulfonyloxy)-xanthen-9-on；(9-Oxoxanthen-1-yl) 4-methylbenzenesulfonate
• CAS: 723250-28-0
• 化学式: C₂₀H₁₄O₅S
• 分子量: 366.394
• InChiKey: SHVSSRSXPOEPOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(toluene-4-sulfonyloxy)-xanthen-9-one 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 Methanesulfonic acid 2-(6-oxa-1,2-diaza-aceanthrylen-2-yl)-ethyl ester
  参考文献：
  名称：

  Design, synthesis, and antiproliferative activity of some novel aminosubstituted xanthenones, able to overcome multidrug resistance toward MES-SA/Dx5 cells

  摘要：

  A series of novel xanthenone aminoderivatives and their pyrazole-fused counterparts possessing structural analogy to the potent anticancer agent 9-methoxypyrazoloacridine (PZA) reported. These compounds exhibited an interesting cytotoxic activity against a panel of cell lines. Most noticeably, they retain activity against the multidrug resistant MES-SA/Dx5 subline, showing resistant factors close to 1. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.079
• 作为产物：
  描述：

  1-Hydroxy-3-tosyloxyxanthon 在 乙醇 、 镍 、 potassium carbonate 、 丙酮 作用下， 生成 1-(toluene-4-sulfonyloxy)-xanthen-9-one
  参考文献：
  名称：

  Jain et al., Journal Of Scientific and Industrial Research, 1953, vol. 12 B, p. 647

  摘要：

  DOI：

文献信息

• Design and synthesis of novel amino-substituted xanthenones and benzo[b]xanthenones: Evaluation of their antiproliferative activity and their ability to overcome multidrug resistance toward MES-SA/D×5 cells
  作者：Ioannis K. Kostakis、Nicole Pouli、Panagiotis Marakos、Alexios-Leandros Skaltsounis、Harris Pratsinis、Dimitris Kletsas

  DOI：10.1016/j.bmc.2005.12.003

  日期：2006.5

  A number of new xanthenone and benzo[b]xanthenone amino derivatives and their pyrazole-fused counterparts have been designed and synthesized possessing structural analogy to the potent anticancer agent 9-methoxypyrazoloacridine. The synthesis of the compounds proceeds through nucleophilic substitution of 1-chloro-4-nitroxanthenone or the corresponding benzo[b]xanthenone by the appropriately substituted

  已经设计并合成了许多新的黄原酮和苯并[b]黄酮酮氨基衍生物及其与吡唑稠合的对应物，它们具有与有效的抗癌剂9-甲氧基吡唑并ac啶相似的结构。化合物的合成是通过用适当取代的胺或肼亲核取代1-氯-4-硝基氧杂蒽酮或相应的苯并[b]噻吨酮，还原硝基，并转化成合适的二烷基氨基乙酰胺。该方法不能用于吡唑稠合的苯并[b]黄酮酮的合成，因此开发了一种不同，简单且高产的合成方法来制备目标分子。新衍生物对鼠白血病L1210细胞系的体外细胞毒性作用，描述了人结肠直肠腺癌（HT-29）和人子宫肉瘤（MES-SA及其对阿霉素变体MES-SA / D x 5的100倍耐药性）细胞系，并与参考药物进行了比较。这些化合物对受试细胞系显示出显着的细胞毒活性，此外，它们还保留了对多重耐药性MES-SA / D x 5亚系的活性，显示出接近1的抗性因子。据发现，许多衍生物具有DNA结合能力。进行标准的溴化乙锭置换试验。大多数研究的化合物诱导了G2
• US4539412A
  申请人：——

  公开号：US4539412A

  公开（公告）日：1985-09-03
• Design, synthesis, and antiproliferative activity of some novel aminosubstituted xanthenones, able to overcome multidrug resistance toward MES-SA/Dx5 cells
  作者：Ioannis K. Kostakis、Roxane Tenta、Nicole Pouli、Panagiotis Marakos、Alexios-Leandros Skaltsounis、Harris Pratsinis、Dimitris Kletsas

  DOI：10.1016/j.bmcl.2005.07.079

  日期：2005.11

  A series of novel xanthenone aminoderivatives and their pyrazole-fused counterparts possessing structural analogy to the potent anticancer agent 9-methoxypyrazoloacridine (PZA) reported. These compounds exhibited an interesting cytotoxic activity against a panel of cell lines. Most noticeably, they retain activity against the multidrug resistant MES-SA/Dx5 subline, showing resistant factors close to 1. (c) 2005 Elsevier Ltd. All rights reserved.
• Jain et al., Journal Of Scientific and Industrial Research, 1953, vol. 12 B, p. 647
  作者：Jain et al.

  DOI：——

  日期：——