3-Bromopropyl 10-chloroanthracene-9-carboxylate | 1208863-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-Bromopropyl 10-chloroanthracene-9-carboxylate
• CAS: 1208863-59-5
• 化学式: C₁₈H₁₄BrClO₂
• 分子量: 377.665
• InChiKey: HIQQTRSLXRDDDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Bromopropyl 10-chloroanthracene-9-carboxylate 、 3-氨基-1-丙醇 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 3-(3-Hydroxypropylamino)propyl 10-chloroanthracene-9-carboxylate
  参考文献：
  名称：

  Structure−Activity Relationships Studies in a Series of N,N-Bis(alkanol)amine Aryl Esters as P-Glycoprotein (Pgp) Dependent Multidrug Resistance (MDR) Inhibitors

  摘要：

  As a continuation Or a previous research, a series of N,N-bis(alkanol)amine aryl esters, as Pgp-dependent MDR inhibitors, was; designed and synthesized. The aromatic ester portions are suitably modulated, and new aryl rings (Ar-1 and Ar-2) were combined with trans-3-(3,4,5-trimethoxyphenyl)-vinyl, 3,4,5-trimethoxybenzyl and anthracene moieties that were present in the most potent previously Studied compounds. The new compounds showed I wide range of potencies and efficacies Oil doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay. Selected compounds (5, 6, 8, 9, and 21) were further Studied, evaluating their action on doxorubicin cytotoxicity potentiation oil K562 cells; they significantly enhanced doxorubicin cytotoxicity oil K562/DOX cells, confirming the results obtained with pirarubicin. Compound 9 Shows file Most promising properties as it was able to nearly completely reverse Pgp-dependent pirarubicin extrusion at nanomolar closes and increased the cytotoxicity of doxorubicin with a reversal fold (RF) of 19.1 at 3 mu M dose.

  DOI：

  10.1021/jm9016174
• 作为产物：
  描述：

  10-chloroanthracene-9-carbonyl chloride 、 3-溴-1-丙醇 以 氯仿 为溶剂， 生成 3-Bromopropyl 10-chloroanthracene-9-carboxylate
  参考文献：
  名称：

  Structure−Activity Relationships Studies in a Series of N,N-Bis(alkanol)amine Aryl Esters as P-Glycoprotein (Pgp) Dependent Multidrug Resistance (MDR) Inhibitors

  摘要：

  As a continuation Or a previous research, a series of N,N-bis(alkanol)amine aryl esters, as Pgp-dependent MDR inhibitors, was; designed and synthesized. The aromatic ester portions are suitably modulated, and new aryl rings (Ar-1 and Ar-2) were combined with trans-3-(3,4,5-trimethoxyphenyl)-vinyl, 3,4,5-trimethoxybenzyl and anthracene moieties that were present in the most potent previously Studied compounds. The new compounds showed I wide range of potencies and efficacies Oil doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay. Selected compounds (5, 6, 8, 9, and 21) were further Studied, evaluating their action on doxorubicin cytotoxicity potentiation oil K562 cells; they significantly enhanced doxorubicin cytotoxicity oil K562/DOX cells, confirming the results obtained with pirarubicin. Compound 9 Shows file Most promising properties as it was able to nearly completely reverse Pgp-dependent pirarubicin extrusion at nanomolar closes and increased the cytotoxicity of doxorubicin with a reversal fold (RF) of 19.1 at 3 mu M dose.

  DOI：

  10.1021/jm9016174