4-溴丁基蒽-9-羧酸酯 | 144449-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 4-溴丁基蒽-9-羧酸酯
• 英文名称: Anthracene-9-carboxylic acid n-bromobutyl ester
• 英文别名: 4-bromobutyl anthracene-9-carboxylate；4-Bromobutyl anthracene-9-carboxylate
• CAS: 144449-72-9
• 化学式: C₁₉H₁₇BrO₂
• 分子量: 357.247
• InChiKey: PDBKCUFIUPRGOO-UHFFFAOYSA-N

物化性质

• 沸点：
  503.1±33.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  4-溴丁基蒽-9-羧酸酯 在 甲酸 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 4-((4-hydroxybutyl)(methyl)amino)butyl anthracene-9-carboxylate
  参考文献：
  名称：

  Multidrug resistance (MDR) reversers: High activity and efficacy in a series of asymmetrical N,N-bis(alkanol)amine aryl esters

  摘要：

  As a continuation of our research on potent and efficacious P-gp-dependent multidrug resistance (MDR) reversers, several new N,N-bis(alkanol)amine aryl esters were designed and synthesized, varying the aromatic moieties or the length of the methylenic chain. The new compounds were tested on doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay, where most of the new compounds were shown to be active. In particular the asymmetrical compounds, characterized by two linkers of different length, generally showed fairly high activities as MDR reversers. Some selected compounds (isomers 15-17) were further studied by evaluating their doxorubicin cytotoxicity enhancement (reversal fold, RF) on the K562/DOX cell line. The results of both pharmacological assays indicate that compounds 16 (GDE6) and 17 (GDE19) could be interesting leads for the development of new P-gp dependent MDR modulators. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.084
• 作为产物：
  描述：

  9-蒽甲酸 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 4-溴丁基蒽-9-羧酸酯
  参考文献：
  名称：

  Multidrug resistance (MDR) reversers: High activity and efficacy in a series of asymmetrical N,N-bis(alkanol)amine aryl esters

  摘要：

  As a continuation of our research on potent and efficacious P-gp-dependent multidrug resistance (MDR) reversers, several new N,N-bis(alkanol)amine aryl esters were designed and synthesized, varying the aromatic moieties or the length of the methylenic chain. The new compounds were tested on doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay, where most of the new compounds were shown to be active. In particular the asymmetrical compounds, characterized by two linkers of different length, generally showed fairly high activities as MDR reversers. Some selected compounds (isomers 15-17) were further studied by evaluating their doxorubicin cytotoxicity enhancement (reversal fold, RF) on the K562/DOX cell line. The results of both pharmacological assays indicate that compounds 16 (GDE6) and 17 (GDE19) could be interesting leads for the development of new P-gp dependent MDR modulators. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.084

文献信息

• Photosensitization of Colloidal Titania Particles by Electron Injection from an Excited Organic Dye−Antennae Function
  作者：Jianjun He、Jincai Zhao、Tao Shen、Hisao Hidaka、Nick Serpone

  DOI：10.1021/jp971550v

  日期：1997.10.1

  Electron transfer from an excited organic dye-antennae device, the diester formed between fluorescein and anthracene-9-carboxylic acid (FL-AN), to colloidal TiO2 particles has been examined by absorption, photoluminescence, and laser flash spectroscopies and by electron spin resonance techniques under steady-state laser excitation. This diester FL-AN is chemisorbed to the TiO2 particles through the phenolic function of the fluorescein moiety; the anthracene component of FL-AN acts as the energy donor component, which is not in contact with the semiconductor particle surface. The apparent association constant (K-app) is ca. 200 mol(-1) L. Exciting the fluorescein side with visible light (around 470 nm) induces electron injection from its singlet excited state onto the conduction band of TiO2 (k(et) = 2.30 x 10(8) s(-1)). Excitation of the anthracene moiety with ultraviolet light (lambda approximate to 355 nm) first causes energy transfer from its singlet excited state to the lowest excited singlet state of fluorescein (Phi(enT) = 0.98, and k(enT) = 2.23 x 10(10) s(-1)), following which electron injection occurs from the fluorescein singlet to the conduction band of TiO2 at a rate otherwise identical to direct excitation of fluorescein. This greatly improves sensitization efficiency in applications to solar energy conversion. Electron spin resonance and laser flash spectroscopies demonstrated formation of the radical cation FL.+-AN on electron injection.
• Multidrug resistance (MDR) reversers: High activity and efficacy in a series of asymmetrical N,N-bis(alkanol)amine aryl esters
  作者：Silvia Dei、Marcella Coronnello、Elisa Floriddia、Gianluca Bartolucci、Cristina Bellucci、Luca Guandalini、Dina Manetti、Maria Novella Romanelli、Milena Salerno、Ivan Bello、Enrico Mini、Elisabetta Teodori

  DOI：10.1016/j.ejmech.2014.09.084

  日期：2014.11

  As a continuation of our research on potent and efficacious P-gp-dependent multidrug resistance (MDR) reversers, several new N,N-bis(alkanol)amine aryl esters were designed and synthesized, varying the aromatic moieties or the length of the methylenic chain. The new compounds were tested on doxorubicin-resistant erythroleukemia K562 cells (K562/DOX) in the pirarubicin uptake assay, where most of the new compounds were shown to be active. In particular the asymmetrical compounds, characterized by two linkers of different length, generally showed fairly high activities as MDR reversers. Some selected compounds (isomers 15-17) were further studied by evaluating their doxorubicin cytotoxicity enhancement (reversal fold, RF) on the K562/DOX cell line. The results of both pharmacological assays indicate that compounds 16 (GDE6) and 17 (GDE19) could be interesting leads for the development of new P-gp dependent MDR modulators. (C) 2014 Elsevier Masson SAS. All rights reserved.