2-ethoxy-5-(3,4,5-trimethoxyphenethyl)phenol | 1221157-00-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-ethoxy-5-(3,4,5-trimethoxyphenethyl)phenol
• 英文别名: 2-ethoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]phenol；3,4,5-trimethoxy-3'-hydroxy-4'-ethoxydiphenylethane；3'-hydroxyl-4'-ethoxy-3,4,5-trimethoxy diphenylethane
• CAS: 1221157-00-1
• 化学式: C₁₉H₂₄O₅
• 分子量: 332.397
• InChiKey: NKGSKXGQKUQZJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethoxy-5-(3,4,5-trimethoxyphenethyl)phenol 在 三乙胺 、 三氯氧磷 作用下， 以50%的产率得到2-ethoxy-5-(3,4,5-trimethoxyphenethyl)phenyl disodium phosphate
  参考文献：
  名称：

  Combretastatin A-4及其衍生物：针对真菌微管蛋白的潜在杀菌剂

  摘要：

  Combretastatin A-4首先从非洲柳树Combretum caffrum中分离出来，是医学上的微管蛋白聚合抑制剂。在本研究中，它首先被假定为潜在的针对真菌微管蛋白的杀菌剂，可用于控制植物病害。合成了Combretastatin A-4及其衍生物，并对其进行了茄枯萎病和稻瘟病菌的抗药性试验。几种化合物的EC 50值类似于或优于异丙基硫烷的EC 50值，后者广泛用于水稻疾病控制。结构-活性关系研究表明顺式康他汀A-4的构型和羟基对于抗真菌作用至关重要。分子建模表明，康布雷他汀A-4和多菌灵在真菌微管蛋白上的结合位点完全不同。这项研究证明了康普他汀A-4及其衍生物对多菌灵耐药菌株的生物活性。结果为杀菌剂发现和杀菌剂抗性管理提供了一种新方法。

  DOI：

  10.1021/acs.jafc.5b05119
• 作为产物：
  描述：

  4-乙氧基-3-甲氧基苯甲醛 在 正丁基锂 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 二苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 苯 为溶剂， 反应 22.17h， 生成 2-ethoxy-5-(3,4,5-trimethoxyphenethyl)phenol
  参考文献：
  名称：

  Design, synthesis and anti-proliferative effects in tumor cells of new combretastatin A-4 analogs

  摘要：

  A total of 11 novel combretastatin A-4 (CA-4) analogs were designed, synthesized, and evaluated for the anti-proliferative effects in tumor cells. The compounds represent four structural classes: (i) hydrogenated derivatives, (ii) ethoxyl derivatives, (iii) amino derivatives and (iv) pro-drugs. Biological evaluations demonstrate that multiple structural features control the biological potency. Three of the compounds, sit-1, sit-2 and sit-3, have potent anti-proliferative activity against multiple cancer cell lines. Their pro-drugs were synthesized to increase water solubility. Structure-activity relationship study and Surflex-Docking were studied in this paper. These results will be useful for the design of new CA-4 analogs that are structurally related to the SAR study. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.05.003

文献信息

• 一种多取代苯酚磷酸酯盐及其制备方法和应用
  申请人：上海应用技术大学

  公开号：CN110642885A

  公开（公告）日：2020-01-03

  本发明涉及一种多取代苯酚磷酸酯盐及其制备方法，包括以下步骤：S1：将多取代的酚类化合物溶解于惰性有机溶剂中，加入缚酸剂，缓慢加入焦磷酰氯，加毕，保温反应2～24h，得到多取代苯酚单磷酸酯前驱体；S2：向多取代苯酚单磷酸酯前驱体中加入有机溶剂A，稀释后滴加无机碱溶液，使水相pH>7，分液，弃去有机相，调节水相pH＝1，加入有机溶剂B进行萃取，合并有机相，浓缩至干，得到多取代苯酚单磷酸酯；S3：用碱液中和，水解，得到多取代苯酚磷酸酯钠盐。与现有技术相比，本发明提供了一种多取代苯酚抗肿瘤药物磷酸酯盐前药合成方法的改进，在合成中具有较好磷酸酯化效果，且路线简单，纯度较高，适合工业化生产。
• 5-FLUOROURACIL DERIVATIVES, PREPARATION METHODS AND USES THEREOF
  申请人：SHANGHAI ECUST BIOMEDICINE CO., LTD.

  公开号：US20210230122A1

  公开（公告）日：2021-07-29

  Disclosed is a 5-fluorouracil derivative having the molecular structure shown in general formula VI, in which Ra and Rb groups are an alkoxy group or a fluorine-substituted alkoxy group having 1, 2, 3, or 4 carbon atoms, and are mono-, bis-, tri-, tetra- or penta-substituted on a phenyl group; a linking group L1 is an alkyl or alkenyl group having 1, 2, 3, or 4 carbon atoms, a linking group L2 is oxygen, or an alkyl or alkoxy group having 1, 2, 3, or 4 carbon atoms, or an amino acid, or an alkyl group having 1, 2, 3, or 4 carbon atoms containing an amino moiety, or a furyl group, and an X group is O or —NH—. Further disclosed is a method for preparing such a derivative and a use of the same in the treatment of cancer, tumor diseases, and diseases caused by abnormal neovascularization in a human or non-human mammal, and a medicament or a composition containing the 5-fluorouracil derivative.

  本发明披露了一种具有分子结构的5-氟尿嘧啶衍生物，通式为VI，其中Ra和Rb基团是具有1、2、3或4个碳原子的烷氧基或氟代烷氧基，并且在苯基上是单、双、三、四或五取代的；连接基L1是具有1、2、3或4个碳原子的烷基或烯基，连接基L2是氧，或具有1、2、3或4个碳原子的烷基或烷氧基，或氨基酸，或含有氨基部分的具有1、2、3或4个碳原子的烷基，或呋喃基，X基是O或—NH—。此外，还披露了一种制备此类衍生物的方法，以及在人类或非人类哺乳动物中治疗癌症、肿瘤疾病和由异常新血管生成引起的疾病中使用该衍生物的用途，以及包含5-氟尿嘧啶衍生物的药物或组合物。
• Design, synthesis and structure–activity relationship studies on erianin analogues as pyruvate carboxylase inhibitors in hepatocellular carcinoma cells
  作者：Hailong Shi、Jinlian Yang、Zeen Qiao、Lingyu Li、Gang Liu、Qi Dai、Li Xu、Wei Jiao、Guolin Zhang、Fei Wang、Xiaoxia Lu、Xiaofeng Ma

  DOI：10.1039/d3ob01114c

  日期：——

  nM) in liver cancer cells with IC50 values of 15.15 nM and 10.05 nM, respectively. Additionally, at a concentration of 10 nM, compounds 35 and 36 inhibited PC with inhibitory rates of 39.10% and 40.15%, respectively, exhibiting nearly identical inhibitory activity to erianin (inhibitory rate of 40.07%). Additionally, a computer simulation docking study demonstrated the basis for better interactions

  基于生物等排原理，通过改变毛兰素的两个芳香环、环上的取代基以及环上的连接基，设计合成了一系列新型毛兰素类似物。该类似物在肝细胞癌细胞中作为丙酮酸羧化酶 (PC) 抑制剂进行了评估。结果发现，用氟取代羟基的化合物35和36在肝癌细胞中表现出比毛兰素更高的活性（IC 50值为17.30 nM），IC 50值分别为15.15 nM和10.05 nM。此外，在10 nM浓度下，化合物35和36对PC的抑制率分别为39.10%和40.15%，表现出与毛兰素几乎相同的抑制活性（抑制率为40.07%）。此外，计算机模拟对接研究证明了受体和配体之间更好相互作用的基础。35的氟原子不仅可以与Lys-1043（NH⋯F，2.04 Å）形成氢键，还可以与Lys-1043（3.67 Å）和Glu-1046（3.70 Å）的羰基形成氟键，由于B环弹头上的卤素的取向不同。相反， 34的氯原子只能与Lys-1043中的
• ETHOXY DIPHENYL ETHANE DERIVATES, PREPARATION PROCESSES AND USES THEREOF
  申请人：Shanghai Ecust Biomedicine Co., Ltd

  公开号：EP2351730B1

  公开（公告）日：2014-07-30
• Design, synthesis and anti-proliferative effects in tumor cells of new combretastatin A-4 analogs
  作者：Lei Zhao、Jiu-Jiu Zhou、Xin-Ying Huang、Li-Ping Cheng、Wan Pang、Zhen-Peng Kai、Fan-Hong Wu

  DOI：10.1016/j.cclet.2015.05.003

  日期：2015.8

  A total of 11 novel combretastatin A-4 (CA-4) analogs were designed, synthesized, and evaluated for the anti-proliferative effects in tumor cells. The compounds represent four structural classes: (i) hydrogenated derivatives, (ii) ethoxyl derivatives, (iii) amino derivatives and (iv) pro-drugs. Biological evaluations demonstrate that multiple structural features control the biological potency. Three of the compounds, sit-1, sit-2 and sit-3, have potent anti-proliferative activity against multiple cancer cell lines. Their pro-drugs were synthesized to increase water solubility. Structure-activity relationship study and Surflex-Docking were studied in this paper. These results will be useful for the design of new CA-4 analogs that are structurally related to the SAR study. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.