3-(3,4-Dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 111797-23-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(3,4-Dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 111797-23-0
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: XCTVYGILKGHJLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3-(3,4-Dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 丙酮 为溶剂， 生成 3-(3,4-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)propan-1-one
  参考文献：
  名称：

  10.1186/s40360-024-00758-2

  摘要：

  DOI：

  10.1186/s40360-024-00758-2
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 3,4-二甲氧基苯甲醛 在 potassium hydroxide 作用下， 生成 3-(3,4-Dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of New <i>N</i>¹-Substituted-5-aryl-3-(3,4,5-trimethoxyphenyl)-2-pyrazoline Derivatives as Antitumor Agents Targeting the Colchicine Site on Tubulin

  摘要：

  合成了一系列与康柏拉斯汀A4（CA-4）结构相关的吡唑啉衍生物2a–e、3a–e和4a–e，并通过光谱学方法和元素分析进行了表征。在这些化合物中，CA-4的顺式双键被吡唑啉环取代，旨在增强CA-4表现出的细胞毒性作用，并防止与CA-4失活相关的顺/反异构化。所有新化合物的细胞毒性活性在体外对MCF-7和HCT-116细胞系进行了研究。对最活跃化合物3d、4a和e的微管聚合抑制作用进行了评估。体外研究表明，化合物4e的细胞毒性与凋亡诱导和caspase-3活化相关，因此指示了这些化合物的抗癌效果的凋亡途径。此外，对合成化合物在小鼠中的埃赫利希腹水癌（EAC）实体肿瘤进行了体内评估。化合物2c、3a和e显示出肿瘤重量显著降低，以及caspase-3表达增加约2–4倍。

  DOI：

  10.1248/bpb.b16-00277

文献信息

• Divergent Strategy for the Diastereoselective Synthesis of the Tricyclic 6,7-Diaryltetrahydro-6<i>H</i>-benzo[<i>c</i>]chromene Core via Pt(IV)-Catalyzed Cycloaddition of <i>o</i>-Quinone Methides and Olefin Ring-Closing Metathesis
  作者：Kassrin Tangdenpaisal、Kanokpish Chuayboonsong、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1021/acs.joc.6b03086

  日期：2017.3.3

  A divergent strategy for the synthesis of the tricyclic 6,7-diaryltetrahydro-6H-benzo[c]chromene core was successfully developed. The 2,3-trans, 2,4-cis trisubstituted chroman moiety was formed via highly efficient and stereoselective Pt(IV)-catalyzed cycloaddition reactions of the corresponding quinone methides with chalcones. Subsequent steps provided the common diene alcohol, which underwent BF3·Et2O-mediated

  成功开发了一种合成三环6,7-二芳基四氢-6 H-苯并[ c ]色烯核心的不同策略。2,3-反式，2,4-顺式三取代的苯并二氢吡喃部分是通过相应的醌甲基化物与查耳酮的高效且立体选择性的Pt（IV）催化的环加成反应形成的。随后的步骤提供了普通的二烯醇，其经过BF 3 ·Et 2 O介导的Et 3 SiH还原和使用Ru（II）催化剂进行的烯烃闭环复分解（RCM）。最后两个步骤的顺序为使C6和C10a处的立体化学结果多样化提供了一种方法。
• Discovery of novel tubulin CBSI <b>(<i>R</i>)-9k</b> from the indanone scaffold for the treatment of colorectal cancer
  作者：Zhipeng Huo、Delin Min、Shijie Zhang、Mei-Lin Tang、Xun Sun

  DOI：10.1039/d3md00337j

  日期：——

  Compared with the first line therapy 5-fluorouracil, (R)-9k bound to the colchicine site and showed more potent inhibitory activities against colorectal cancer cells, lower cytotoxicity against normal cells and less cardiotoxicity.

  与一线疗法 5-氟尿嘧啶相比，(R)-9k 与秋水仙碱位点结合，对结直肠癌细胞的抑制活性更强，对正常细胞的细胞毒性更低，心脏毒性更小。
• Identification of 3′,4′,5′-trimethoxychalcone analogues as potent inhibitors of Helicobacter pylori-induced inflammation in human gastric epithelial cells
  作者：Chih-Ho Lai、Yerra Koteswara Rao、Shih-Hua Fang、Yu-Ting Sing、Yew-Min Tzeng

  DOI：10.1016/j.bmcl.2010.07.094

  日期：2010.9

  Efforts to identify potent small molecule inhibitors of Helicobacter pylori led to the evaluation of 23 3',4',5'-trimethoxychalcone analogues. Some of the compounds displayed potent antibacterial activity against H. pylori. Three most active and selective compounds 1, 7, and 13 also showed the bactericide activity against the reference as well as multidrug-resistant strains of H. pylori. Additionally, the aforementioned three compounds potentially inhibited the H. pylori adhesion and invasion to human gastric epithelial (AGS) cells. Furthermore, these selective compounds inhibited the H. pylori-induced gastric inflammation by reduced inflammatory mediator's nuclear factor kappa B activation, and the secretion of interleukin-8. (c) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of New &lt;i&gt;N&lt;/i&gt;&lt;sup&gt;1&lt;/sup&gt;-Substituted-5-aryl-3-(3,4,5-trimethoxyphenyl)-2-pyrazoline Derivatives as Antitumor Agents Targeting the Colchicine Site on Tubulin
  作者：Salwa Elmeligie、Nadia Abdalla Khalil、Eman Mohamed Ahmed、Soha Hussein Emam、Sawsan Abo-Bakr Zaitone

  DOI：10.1248/bpb.b16-00277

  日期：——

  A series of pyrazoline derivatives 2a–e, 3a–e and 4a–e structurally related to combretastatin A4 (CA-4) were synthesized and characterized by spectroscopic means and elemental analyses. In these compounds, the cis double bond of CA-4 was replaced with the pyrazoline ring aiming to enhance the cytotoxic effects displayed by CA-4 and to prevent the cis/trans isomerization that is associated with inactivation of CA-4. The cytotoxic activity of all new compounds was investigated in vitro against MCF-7 and HCT-116 cell lines. The inhibition of tubulin polymerization by the most active compounds 3d, 4a and e was evaluated. The cytotoxicity of 4e was correlated with induction of apoptosis and caspase-3 activation in vitro thus indicating the apoptotic pathway of anticancer effect of these compounds. Furthermore, in vivo evaluation of the synthesized compounds was carried out against Ehrlich’s ascites carcinoma (EAC) solid tumor grown in mice. Compounds 2c, 3a and e showed significant reduction in tumor weight, and about 2–4 fold increase in caspase-3 expression.

  合成了一系列与康柏拉斯汀A4（CA-4）结构相关的吡唑啉衍生物2a–e、3a–e和4a–e，并通过光谱学方法和元素分析进行了表征。在这些化合物中，CA-4的顺式双键被吡唑啉环取代，旨在增强CA-4表现出的细胞毒性作用，并防止与CA-4失活相关的顺/反异构化。所有新化合物的细胞毒性活性在体外对MCF-7和HCT-116细胞系进行了研究。对最活跃化合物3d、4a和e的微管聚合抑制作用进行了评估。体外研究表明，化合物4e的细胞毒性与凋亡诱导和caspase-3活化相关，因此指示了这些化合物的抗癌效果的凋亡途径。此外，对合成化合物在小鼠中的埃赫利希腹水癌（EAC）实体肿瘤进行了体内评估。化合物2c、3a和e显示出肿瘤重量显著降低，以及caspase-3表达增加约2–4倍。
• 10.1186/s40360-024-00758-2
  作者：Li, Peng、Tian, Xiangjuan、Zhang, Die、Ou, Huiping、Huang, Qiufeng、Jin, Wenbin、Liu, Ran

  DOI：10.1186/s40360-024-00758-2

  日期：——