triphenyl(11-((3,4,5-trihydroxybenzoyl)oxy)-undecyl)phosphonium bromide | 1581234-55-0

• 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: triphenyl(11-((3,4,5-trihydroxybenzoyl)oxy)-undecyl)phosphonium bromide
• 英文别名: triphenyl(11-((3,4,5-trihydroxybenzoyl)oxy)undecyl)phosphonium bromide；Triphenyl-[11-(3,4,5-trihydroxybenzoyl)oxyundecyl]phosphanium;bromide；triphenyl-[11-(3,4,5-trihydroxybenzoyl)oxyundecyl]phosphanium;bromide
• CAS: 1581234-55-0
• 化学式: Br*C₃₆H₄₂O₅P
• 分子量: 665.604
• InChiKey: PJDDKBBWMSSINE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  没食子酸 、 (11-hydroxyundecyl)triphenylphosphonium bromide 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 乙腈 为溶剂， 以192 mg的产率得到triphenyl(11-((3,4,5-trihydroxybenzoyl)oxy)-undecyl)phosphonium bromide
  参考文献：
  名称：

  从苯甲酸衍生的亲脂性阳离子的连续流动合成作为人头颈癌细胞系中的新细胞毒性化学实体

  摘要：

  连续流动化学用于合成一系列离域亲脂性三苯基鏻阳离子 (DLC)，这些阳离子通过酯官能团与几种羟基化苯甲酸衍生物相连，并在反应时间和选择性方面进行评估。合成的化合物在头颈部肿瘤细胞系中显示出细胞毒活性和选择性。分子的作用机制涉及线粒体解偶联效应和细胞内 ATP 产生和细胞凋亡诱导的减少。

  DOI：

  10.1039/d0md00153h

文献信息

• Antiproliferative and Uncoupling Effects of Delocalized, Lipophilic, Cationic Gallic Acid Derivatives on Cancer Cell Lines. Validation in Vivo in Singenic Mice
  作者：José A. Jara、Vicente Castro-Castillo、Jorge Saavedra-Olavarría、Liliana Peredo、Mario Pavanni、Fabián Jaña、María Eugenia Letelier、Eduardo Parra、María Inés Becker、Antonio Morello、Ulrike Kemmerling、Juan Diego Maya、Jorge Ferreira

  DOI：10.1021/jm500174v

  日期：2014.3.27

  Tumor cells principally exhibit increased mitochondrial transmembrane potential (ΔΨ(m)) and altered metabolic pathways. The therapeutic targeting and delivery of anticancer drugs to the mitochondria might improve treatment efficacy. Gallic acid exhibits a variety of biological activities, and its ester derivatives can induce mitochondrial dysfunction. Four alkyl gallate triphenylphosphonium lipophilic cations were synthesized, each differing in the size of the linker chain at the cationic moiety. These derivatives were selectively cytotoxic toward tumor cells. The better compound (TPP(+)C10) contained 10 carbon atoms within the linker chain and exhibited an IC50 value of approximately 0.4-1.6 μM for tumor cells and a selectivity index of approximately 17-fold for tumor compared with normal cells. Consequently, its antiproliferative effect was also assessed in vivo. The oxygen consumption rate and NAD(P)H oxidation levels increased in the tumor cell lines (uncoupling effect), resulting in a ΔΨ(m) decrease and a consequent decrease in intracellular ATP levels. Moreover, TPP(+)C10 significantly inhibited the growth of TA3/Ha tumors in mice. According to these results, the antineoplastic activity and safety of TPP(+)C10 warrant further comprehensive evaluation.
• Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines
  作者：Mabel Catalán、Vicente Castro-Castillo、Javier Gajardo-de la Fuente、Jocelyn Aguilera、Jorge Ferreira、Ricardo Ramires-Fernandez、Ivonne Olmedo、Alfredo Molina-Berríos、Charlotte Palominos、Marcelo Valencia、Marta Domínguez、José A. Souto、José A. Jara

  DOI：10.1039/d0md00153h

  日期：——

  Continuous flow chemistry was used for the synthesis of a series of delocalized lipophilic triphenylphosphonium cations (DLCs) linked by means of an ester functional group to several hydroxylated benzoic acid derivatives and evaluated in terms of both reaction time and selectivity. The synthesized compounds showed cytotoxic activity and selectivity in head and neck tumor cell lines. The mechanism of

  连续流动化学用于合成一系列离域亲脂性三苯基鏻阳离子 (DLC)，这些阳离子通过酯官能团与几种羟基化苯甲酸衍生物相连，并在反应时间和选择性方面进行评估。合成的化合物在头颈部肿瘤细胞系中显示出细胞毒活性和选择性。分子的作用机制涉及线粒体解偶联效应和细胞内 ATP 产生和细胞凋亡诱导的减少。