(3,5-dimethoxybenzyl)triphenylphosphonium bromide | 24131-30-4

• 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: (3,5-dimethoxybenzyl)triphenylphosphonium bromide
• 英文别名: (3,5-dimethoxyphenyl)methyl-triphenylphosphanium;bromide
• CAS: 24131-30-4
• 化学式: Br*C₂₇H₂₆O₂P
• 分子量: 493.38
• InChiKey: JMJMXUZILDIHQD-UHFFFAOYSA-M

物化性质

• 熔点：
  275 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,5-dimethoxybenzyl)triphenylphosphonium bromide 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1,3-二甲氧基-5-(5-羟基戊基)苯
  参考文献：
  名称：

  Identification of Novel ROS Inducers: Quinone Derivatives Tethered to Long Hydrocarbon Chains

  摘要：

  We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 mu M) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 mu M) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.

  DOI：

  10.1021/jm501846y
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.5h， 生成 (3,5-dimethoxybenzyl)triphenylphosphonium bromide
  参考文献：
  名称：

  吲哚和吲唑基二苯乙烯的设计、合成和细胞毒活性

  摘要：

  为了开发天然存在的二苯乙烯支架衍生的新型高效抗癌剂，根据分子杂交策略设计并通过 Witting 反应合成了总共 24 种吲唑和吲唑类二苯乙烯类化合物，包括 17 种新化合物。针对人类肿瘤细胞系（K562 细胞和 MDA-MB-231 细胞）的细胞毒性筛选结果表明，基于吲哚和吲唑的二苯乙烯类化合物对于开发抗癌剂具有重要意义，因为八种衍生物具有很强的抗增殖活性，IC 为50值小于 10 μM，并且这些合成衍生物对 K562 细胞表现出比 MDA-MB-231 细胞更高的细胞毒性。特别是，基于吲哚的二苯乙烯基哌啶对 K562 和 MDA-MB-231 细胞表现出最有效的细胞毒性，IC 50 值分别为2.4 μM 和 2.18 μM，并且对人正常 L-02 细胞具有显着的选择性。总之，结果表明基于吲哚和吲唑的二苯乙烯是有前途的抗癌支架，值得进一步研究。

  DOI：

  10.1002/cbdv.202300368

文献信息

• Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters
  作者：Jan Pokorný、Denisa Olejníková、Ivo Frydrych、Barbora Lišková、Soňa Gurská、Sandra Benická、Jan Šarek、Jana Kotulová、Marián Hajdúch、Petr Džubák、Milan Urban

  DOI：10.1016/j.ejmech.2021.113706

  日期：2021.11

  synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle

  通过将桦木酸氧化为 30-氧代桦木酸，然后进行 Wittig 反应，合成了一组新的取代二烯。在八种癌细胞系和两种非癌成纤维细胞中体外测试了所有化合物的细胞毒性。几乎所有的二烯都比桦木酸更具细胞毒性。化合物4.22、4.30、4.33、4.39的IC 50低于5 μmol / L ；选择4.22和4.39进行作用机制研究。细胞周期分析显示在 5 × IC 50时凋亡细胞数量增加浓度，其中可以预期导致细胞死亡的不可逆变化的激活。既4.22和4.39导致细胞在用DNA / RNA合成的部分抑制的G0 / G1期的累积为1×IC 50，并在5几乎完全抑制×IC 50。有趣的是，化合物4.39 在 5 × IC 50导致细胞在 S 期积累。较高浓度的受试药物可能比较低浓度抑制更多的脱靶。破坏细胞代谢的机制可以诱导细胞在 S 期的积累。化合物4.22和4.39 均在癌细胞中引发选择性凋亡通过内在途径，
• [EN] FGFR4 INHIBITORS<br/>[FR] INHIBITEURS DU RÉCEPTEUR FGFR4
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2016164703A1

  公开（公告）日：2016-10-13

  Methods, compounds, pharmaceutical compositions, and methods of preparing medicaments for treating hepatocellular carcinoma having an altered FGFR4 and/or FGF19 status.

  治疗肝细胞癌的方法、化合物、药物组合物以及制备药物的方法，其中肝细胞癌具有改变的FGFR4和/或FGF19状态。
• STILBENE DERIVATIVES AS NEW CANCER THERAPEUTIC AGENTS
  申请人：Lee Ruey-min

  公开号：US20080261982A1

  公开（公告）日：2008-10-23

  Stilbene derivatives exhibit killing and suppression of growth activity against a variety of cancer cells, and are effective at suppressing tumor growth in vivo. The stilbene derivatives may be used in the treatment of diseases characterized by cell hyperproliferation including human malignancies and non-malignant diseases such as liver cirrhosis. Stilbenes may also disrupt abnormal vessels in tumor to achieve vascular disrupting effect to suppress tumor growth. Water soluble pro-drug forms of stilbene derivatives are particularly useful in suppressing tumor growth in vivo.

  Stilbene衍生物表现出对多种癌细胞的杀灭和抑制生长活性，并且在体内有效地抑制肿瘤生长。Stilbene衍生物可用于治疗以细胞过度增殖为特征的疾病，包括人类恶性肿瘤和非恶性疾病，如肝硬化。Stilbenes也可以破坏肿瘤中的异常血管，实现血管破坏效应以抑制肿瘤生长。水溶性的Stilbene衍生物前药形式在体内抑制肿瘤生长方面特别有用。
• Novel Resveratrol-Based Substrates for Human Hepatic, Renal, and Intestinal UDP-Glucuronosyltransferases
  作者：Aleksandra K. Greer、Nikhil R. Madadi、Stacie M. Bratton、Sarah D. Eddy、Zofia Mazerska、Howard P. Hendrickson、Peter A. Crooks、Anna Radominska-Pandya

  DOI：10.1021/tx400408x

  日期：2014.4.21

  majority of the hydroxyl groups blocked by methylation and the addition of other novel functional groups as part of a drug optimization program. The activities of recombinant human UGTs from the 1A and 2B families were examined for their capacity to metabolize these compounds. Glucuronide formation was identified using HPLC and verified by β-glucuronidase hydrolysis and LC–MS/MS analysis. NI-12a was glucuronidated

  反式白藜芦醇 (tRes) 已被证明具有强大的抗氧化、抗炎、抗癌和抗衰老特性；然而，它作为治疗剂的使用受到 UDP-葡萄糖醛酸转移酶 (UGT) 快速代谢为其结合形式的限制。当前研究的目的是检验以下假设：tRes 的有限生物利用度可以通过修改其结构来产生类似物，该类似物的葡萄糖醛酸化率低于 tRes 本身。在这项工作中，三种合成的芪类化合物，( E )-3-(3-羟基-4-甲氧基苯基)-2-(3,4,5-三甲氧基苯基)丙烯酸 (NI-12a)，( E )-2,4 -二甲氧基-6-(4-甲氧基苯乙烯基)苯甲醛肟 (NI-ST-05)，和 ( E)-4-(3,5-二甲氧基苯乙烯基)-2,6-二硝基苯酚 (DNR-1)，基于 tRes 的结构设计并在我们实验室合成。UGT 识别 tRes 并在其芳环上连接的 3 个羟基中的每一个上进行葡萄糖醛酸化。因此，上述每种化合物的设计都将大部分羟基通过甲基
• An expedient synthesis of 5-<i>n</i>-alkylresorcinols and novel 5-<i>n</i>-alkylresorcinol haptens
  作者：Kirsti Parikka、Kristiina Wähälä

  DOI：10.3762/bjoc.5.22

  日期：——

  The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C₂₃ and C₂₅ analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semi-stabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

  描述了通过一种新颖的Wittig反应改进合成生物活性长烷基链5-烷基间苯二酚，这种物质存在于全谷物产品中。合成了黑麦和小麦中所有主要的长链5-烷基间苯二酚，包括C23和C25类似物以及以前未制备的半抗原。在水中，半稳定叶立德和烷醛的微波促进反应在加压和开放系统中均获得良好产率。另一种微波促进合成方法是从非稳定的烷基三苯基膦盐和3,5-二甲氧基苯甲醛出发。即使起始材料在水中不溶解，水介质也适用于这些反应。5-烷基间苯二酚是全谷物摄入的潜在生物标志物，而新的5-烷基间苯二酚半抗原衍生物将为烷基间苯二酚的免疫化学检测技术打开道路。