1-(4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one | 105686-92-8

• 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: 1-(4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one
• 英文别名: 1-p-Tolyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；1-(4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 105686-92-8
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: OSPIHNUGEOGEEL-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  471.8±45.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以82%的产率得到3-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of new 4,5-dihydropyrazole derivatives

  摘要：

  A series of 3,5-diaryl-4,5-dihydropyrazole regioisomers, and their 1-acetylated derivatives, bearing a 3,4,5-trimethoxyphenyl moiety combined with a variety of substituted phenyl rings, was synthesized and evaluated for antitumor activity. Results of the in vitro assay against a non-small cell lung carcinoma cell line (NCI-H460) showed several compounds to be endowed with cytotoxicity in micromolar to sub-micromolar range, depending on substitution pattern and position of aryl rings on 4,5-dihydropyrazole core. Potent and selective activity was also observed in the NCI 60 human cancer cell line panel. 5-(3,4,5-Trimethoxyphenyl) pyrazolines 31 and 39 were found to possess potent antiproliferative activity against SR and MDA-MB-435, with GI(50) inhibitory values in nanomolar range. Structure-activity relationships revealed that introduction of a (hydroxy) acetyl group at N-1 of inactive 5-(3,4,5-trimethoxyphenyl) pyrazolines, results in a clear in vitro activating effect. Compound 31 (IC(50) = 5.16 mu M) showed inhibition of tubulin polymerization comparable to that of CA-4 (IC(50) = 4.92 mu M). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.037
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 对甲基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one
  参考文献：
  名称：

  在介孔石墨氮化碳上修饰的单分散NiPd合金纳米粒子，作为高效化学选择性还原α，β-不饱和酮化合物的催化剂

  摘要：

  本文中，研究报告称，通过在介孔石墨氮化碳上装饰NiPd合金纳米粒子的催化剂（NiPd / mpg-C 3 N 4）催化转移各种α，β-不饱和酮，可实现非凡的化学选择性还原（> 99％）。）在水/甲醇介质中的温和条件下。通过在硼烷-叔丁胺的帮助下在油胺（OAm）溶液中还原金属盐，合成NiPd合金NP ，然后通过液相自组装法在mpg-C 3 N 4上修饰。通过TEM，XRD和ICP-MS对NiPd / mpg-C 3 N 4纳米催化剂进行了表征。NiPd / mpg-C 3 N4纳米催化剂是用于化学选择性还原α，β-不饱和酮的高活性催化剂，所有有机化合物均以高收率和99％的选择性转化。另外，该催化剂可以重复使用五次而不会显着降低反应产率。

  DOI：

  10.1039/d0nj03104f

文献信息

• Lewis acid catalyst system for Claisen-Schmidt reaction under solvent free condition
  作者：Chandni G. Halpani、Satyendra Mishra

  DOI：10.1016/j.tetlet.2020.152175

  日期：2020.7

  function as an efficient catalyst system for one-pot Claisen-Schmidt condensation under neat conditions. Substituted acetophenones and benzaldehydes were coupled in situ to afford their corresponding chalcones in excellent yields. The method, with a broad range of substrate tolerance and mild operational conditions can produce assorted chalcone derivatives in moderate to high yields from easily accessible

  建立了Ca（OTf）2与NBu 4 .BF 4的结合，以在纯净条件下用作一锅Claisen-Schmidt冷凝的有效催化剂体系。取代的苯乙酮和苯甲醛在原位偶联，以优异的产率得到它们相应的查耳酮。该方法具有广泛的底物耐受性和温和的操作条件，可以从容易获得的起始原料以中等到高产率生产各种查尔酮衍生物。
• Synthesis and Anticancer Activity of 3-(Substituted Aroyl)-4-(3,4,5-trimethoxyphenyl)-1<i>H</i>-pyrrole Derivatives
  作者：Xiao-Ping Zhan、Lan Lan、Shuai Wang、Kai Zhao、Yu-Xuan Xin、Qi Qi、Yao-Lin Wang、Zhen-Min Mao

  DOI：10.1002/cbdv.201600219

  日期：2017.2

  A series of 3-(substituted aroyl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrrole derivatives were synthesized and determined for their anticancer activity against eleven cancer cell lines and two normal tissue cell lines using MTT assay. Among the synthesized compounds, compound 3f was the most potent compound against A375, CT-26, HeLa, MGC80-3, NCI-H460 and SGC-7901 cells (IC50 = 8.2 - 31.7 μm); 3g, 3n and

  合成了一系列3-（取代的芳酰基）-4-（3,4,5-三甲氧基苯基）-1H-吡咯衍生物，并使用MTT法测定了它们对十一种癌细胞系和两种正常组织细胞系的抗癌活性。在合成的化合物中，化合物3f是针对A375，CT-26，HeLa，MGC80-3，NCI-H460和SGC-7901细胞的最有效化合物（IC50 = 8.2-31.7μm）；3g，3n和3a分别是对抗CHO（IC50 = 8.2μm），HCT-15（IC50 = 21μm）和MCF-7细胞（IC50 = 18.7μm）最有效的化合物。重要的是，所有目标化合物都没有表现出对正常组织细胞的细胞毒性（IC50> 100μm）。因此，这些具有有效的抗癌活性和低毒性的化合物具有开发新的抗癌化学治疗剂的潜力。
• A New Series of Cytotoxic Pyrazoline Derivatives as Potential Anticancer Agents that Induce Cell Cycle Arrest and Apoptosis
  作者：Hong Wang、Jinhong Zheng、Weijie Xu、Cheng Chen、Duncan Wei、Wenxiu Ni、Ying Pan

  DOI：10.3390/molecules22101635

  日期：——

  A new series of pyrazoline derivatives 1b-12b was designed, synthesized and evaluated for antiproliferative activity against three cancer cell lines (HepG-2, Hela and A549). Additionally, NIH/3T3 cell cytotoxicity were tested and the structure activity relationships (SARs) were also determined. Among these new derivatives, the compounds 3-(4-fluorophenyl)-5-(3,4,5-trimethoxythiophenyl)-4,5-dihydro

  设计，合成并评价了一系列新的吡唑啉衍生物1b-12b对三种癌细胞系（HepG-2，Hela和A549）的抗增殖活性。此外，测试了NIH / 3T3细胞的细胞毒性，并确定了结构活性关系（SAR）。在这些新衍生物中，化合物3-（4-氟苯基）-5-（3,4,5-三甲氧基硫代苯基）-4,5-二氢-1H-吡唑-1-碳硫酰胺（1b）和3-（4-氯苯基） ）-5-（3,4,5-三甲氧基噻吩）-4,5-二氢-1H-吡唑-1-碳硫酰胺（2b）对HepG-2细胞表现出最佳活性，IC50值为6.78μM和16.02μM，分别。他们还显示出对Hela细胞的有效活性。同时，3-（4-氯苯基）-5-（3-溴-4-羟基-5-甲氧基硫苯基）-4，5-二氢-1H-吡唑-1-碳硫酰胺（5b）和3-（4-溴-苯基）-5-（3-溴-4-羟基-5-甲氧基硫代苯基）-4,5-二氢-1H-吡唑与顺铂（IC50 = 29.48μM）相比
• Targeting microbial resistance: Synthesis, antibacterial evaluation, DNA binding and modeling study of new chalcone-based dithiocarbamate derivatives
  作者：Marwa Ayman、Shahenda M. El-Messery、Elsayed E. Habib、Sara T. Al-Rashood、Abdulrahman A. Almehizia、Hamad M. Alkahtani、Ghada S. Hassan

  DOI：10.1016/j.bioorg.2019.01.001

  日期：2019.4

  Molecular docking study showed that 20, 22, 24 and 25 had good binding affinity with active site residues via Thr280. DNA macromolecule was further targeted. Compounds 28 and 34 were recorded to have better DNA binding than doxurubucin with IC50 of 27.48 and 30.97 µg/ml respectively, suggesting that it could have a role in their higher antibacterial effect. Their docking into DNA has shown a clear

  合成了新的基于二硫代氨基甲酸酯查尔酮的衍生物，使用不同的光谱技术阐明了它们的结构。对他们进行了针对所选革兰氏阴性细菌的抗菌筛选，重点是微生物抵抗力。通过磷酸乙醇胺转移酶靶向细菌耐药性。大多数合成的化合物显示出与大肠菌素标准品相同或更高的活性。化合物24被证明是活性最高的候选物，对Ps12和K4的MIC为8 µg / ml，对Ps12的MBC为32 µg / ml，对K4的MBC为16 µg / ml。分子对接研究显示20、22、24和25通过Thr280与活性位点残基具有良好的结合亲和力。DNA大分子被进一步靶向。记录的化合物28和34与阿霉素相比具有更好的DNA结合，IC50为27.48和30。分别为97 µg / ml，表明它可能具有较高的抗菌作用。它们与DNA的对接已显示出与抗菌数据相匹配的清晰插值。活性化合物的药代动力学参数表明它们通过GIT具有更好的吸收。
• Synthesis and biological evaluation of pyrimidine bridged combretastatin derivatives as potential anticancer agents and mechanistic studies
  作者：Bhupinder Kumar、Praveen Sharma、Vivek Prakash Gupta、Madhu Khullar、Sandeep Singh、Nilambra Dogra、Vinod Kumar

  DOI：10.1016/j.bioorg.2018.02.027

  日期：2018.8

  evaluation of these compounds showed that selective cancer cell toxicity (in vitro using human lung and breast cancer cell lines) might be due to the inhibition of antioxidant enzymes instigating elevated ROS levels which triggers intrinsic apoptotic pathways. These compounds were found nontoxic to the normal human primary cells. Compound 4a, was found to be competitive inhibitor of colchicine and in

  使用MTT分析法设计，合成和评估了许多嘧啶桥联的康他汀衍生物，并评估了它们对乳腺癌（MCF-7）和肺癌（A549）细胞系的抗癌活性。大多数合成的化合物显示出良好的抗癌活性，其IC 50值在低微摩尔范围内。化合物4a和4p在该系列中最有效，对MCF7和A549癌细胞系的IC 50值分别为4.67 µM和3.38 µM和4.63 µM和3.71 µM。这些化合物的生物学评估表明，选择性癌细胞毒性（体外使用人肺癌和乳腺癌细胞系）可能是由于抗氧化剂酶的抑制导致ROS水平升高，从而触发了内在的凋亡途径。发现这些化合物对正常人原代细胞无毒。发现化合物4a是秋水仙碱的竞争性抑制剂，并且在微管蛋白结合测定中显示出与秋水仙碱相当的微管蛋白聚合抑制潜能。分子模型研究还表明，合成的化合物很好地适合秋水仙碱结合袋。