ethyl 2-(3,4,5-trimethoxyphenoxy)acetate | 65876-11-1

• 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: ethyl 2-(3,4,5-trimethoxyphenoxy)acetate
• 英文别名: 3,4,5-Trimethoxyphenoxyessigsaeureaethylester；Ethyl 3,4,5-trimethoxyphenoxy acetate
• CAS: 65876-11-1
• 化学式: C₁₃H₁₈O₆
• mdl: MFCD27067216
• 分子量: 270.282
• InChiKey: JLAFAKCVFRVYGU-UHFFFAOYSA-N

物化性质

• 熔点：
  51-53 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  148-150 °C(Press: 2 Torr)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3,4,5-trimethoxyphenoxy)acetate 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N,N'-(disulfanediylbis(ethane-2,1-diyl))bis(2-(3,4,5-trimethoxyphenoxy)acetamide)
  参考文献：
  名称：

  Design, synthesis and biological evaluation of oxime lacking Psammaplin inspired chemical libraries as anti-cancer agents

  摘要：

  DOI：

  10.1016/j.molstruc.2020.129173
• 作为产物：
  描述：

  3,4,5-trimethoxyphenoxyacetic acid 在 potassium carbonate 、 二乙胺 作用下， 以 丙酮 为溶剂， 生成 ethyl 2-(3,4,5-trimethoxyphenoxy)acetate
  参考文献：
  名称：

  Basic amides of 3,4,5-trimethoxyphenoxyacetic acid; Synthesis and pharmacology of trimethophenoxamide and analogues

  摘要：

  DOI：

  10.1135/cccc19773628

文献信息

• Palladium-Catalyzed Carbonylative Cyclization of Aryl Alkenes/Alkenols: A New Reaction Mode for the Synthesis of Electron-Rich Chromanes
  作者：Shuang Li、Fuzhuo Li、Jianxian Gong、Zhen Yang

  DOI：10.1021/acs.orglett.5b00214

  日期：2015.3.6

  The Pd(II)-catalyzed intramolecular carbonylative cyclization reaction of aryl alkenes and aryl alkenols is reported for the synthesis of structurally diverse chromanes. PdCl2(CH3CN)2 was used as the catalyst and CuCl2 as the oxidant under the balloon pressure of CO. The reaction is conducted under mild conditions, and chromane-type esters and lactones can be generated in a highly regio- and stereoselective

  据报道，Pd（II）催化的芳基烯烃和芳基烯醇的分子内羰基化环化反应可合成结构多样的苯并二氢吡喃。在CO的球囊压力下，将PdCl 2（CH 3 CN）2用作催化剂，将CuCl 2用作氧化剂。反应在温和的条件下进行，并且可以在高区域和高纯度下生成苯并二氢吡喃型酯和内酯。立体选择性的方式。
• Reverse hydroxamate inhibitors of matrix metalloproteinases
  申请人：——

  公开号：US20020007060A1

  公开（公告）日：2002-01-17

  Compounds having the formula 1 are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.

  具有公式1的化合物是基质金属蛋白酶抑制剂。还披露了基质金属蛋白酶抑制剂组合物和在哺乳动物中抑制基质金属蛋白酶的方法。
• Concise synthesis and preliminary biological evaluation of new triazolylthioacetone derivatives bearing pyridine, pyrazine, and 3,4,5-trimethoxybenzyl fragment
  作者：Lin Chen、Bei Zhang、Yan-Hong Li、Xian-Sen Huo、Wen-Wei You、Pei-Liang Zhao

  DOI：10.1016/j.bmcl.2022.128721

  日期：2022.6

  Based on our previous work, a series of novel triazolylthioacetones incorporating pyridine, pyrazine, and 3,4,5-trimethoxybenzyl fragment were synthesized, and evaluated for antiproliferative activities and interactions with tubulin. Some analogues exhibited moderate to excellent potency, with the most promising compound IIc possessing IC50 values of 0.62, 1.46, and 3.65 μM against HT-29, HCT116, and

  基于我们之前的工作，合成了一系列包含吡啶、吡嗪和 3,4,5-三甲氧基苄基片段的新型三唑基硫代丙酮，并评估了其抗增殖活性和与微管蛋白的相互作用。一些类似物表现出中等至极好的效力，最有希望的化合物IIc对 HT-29、HCT116 和 HepG2 肿瘤细胞的IC 50值分别为 0.62、1.46 和 3.65 μM，与阳性对照 CA-4 相当. 机制研究表明，IIc浓度依赖性地导致 HCT116 肿瘤细胞 G 2 /M 期的细胞周期停滞，并显示显着抑制微管蛋白聚合的 IC 50值为 12.7 μM。此外，分子对接分析表明，IIc 可以以与典型的微管蛋白聚合 抑制剂类似的方式占据秋水仙碱结合位点。这些结果突出了 4-氨基-三唑基硫代丙酮支架作为开发高效抗癌剂的潜在微管蛋白聚合抑制剂。
• Discovery of novel 6-p-tolyl-3-(3,4,5-trimethoxybenzyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivative as a potent tubulin inhibitor with promising in vivo antitumor activity
  作者：Tangyang Ji、Xieer Jian、Lin Chen、Wenbin Zeng、Xiansen Huo、Mingxia Li、Peng Chen、Yuqi Zhang、Wenwei You、Peiliang Zhao

  DOI：10.1016/j.ejmech.2023.115437

  日期：2023.8

  effect. Meanwhile, B5 exerted significant antivascular activity in the wound-healing and tube formation assays. Most importantly, B5 remarkably inhibited tumor growth without obvious signs of toxicity in A549-xenograft mice model. These observations indicate that 6-p-tolyl-3-(3,4,5-trimethoxybenzyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine might be considered as the potential lead compound to develop

  在我们之前的研究的基础上，通过直接闭环策略设计并成功实现了一系列新型三甲氧基苯氧基甲基和三甲氧基苄基取代的三唑并噻二嗪化合物。初步生物学评估表明，最活跃的衍生物B 5对 HeLa、HT-29 和 A549 表现出显着的细胞生长抑制活性，IC 50值分别为 0.046、0.57 和 0.96 μM，这与 CA- 4. 机制研究表明，B 5引起G 2 /M期阻滞，以浓度依赖性方式诱导HeLa细胞凋亡，并显示出有效的微管蛋白聚合抑制作用。同时，乙5在伤口愈合和管形成测定中发挥了显着的抗血管活性。最重要的是， B 5在A549-异种移植小鼠模型中显着抑制肿瘤生长而没有明显的毒性迹象。这些观察结果表明 6-p-tolyl-3-(3,4,5-trimethoxybenzyl)-7 H -[1,2,4]triazolo[3,4- b ][1,3,4]thiadiazine 可能是被认为是开发对正常人体细
• Synthesis and Insect Antifeedant Activity of Aurones against <i>Spodoptera litura</i> Larvae
  作者：Masanori Morimoto、Hiromi Fukumoto、Toki Nozoe、Ai Hagiwara、Koichiro Komai

  DOI：10.1021/jf062562t

  日期：2007.2.1

  A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 mu mol/cm(2). The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3',4',5'-trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED(50)) and a hydrogen-bonding parameter calculated from the R-f value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.