(E)-1-phenyl-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one | 1393480-79-9

• 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: (E)-1-phenyl-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-3-(2,4,5-trimethoxyphenyl)1-phenyl-prop-2-en-1-one；(2E)-1-phenyl-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1393480-79-9
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: SSCWRHWOQOBLJF-MDZDMXLPSA-N

物化性质

• 沸点：
  463.3±45.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (E)-1-phenyl-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one 在 sodium hydride 、 三乙基硼氢化钠 、 C₃₉H₃₂OP₂*Co⁽²⁺⁾*2Cl^(1-) 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 、 mineral oil 为溶剂， 反应 13.5h， 生成
  参考文献：
  名称：

  配体控制的钴催化乙烯基环丙烷的区域发散和立体选择性开环异构化

  摘要：

  利用钴催化开发了乙烯基环丙烷的配体控制区域发散和立体选择性开环异构化。使用市售的 Xantphos 配体，该反应仅提供直链型 1,3-二烯作为产物。有趣的是，当将配体转换为酰胺基二膦配体（PNP）时，得到了具有高区域选择性和立体选择性的支链型1,3-二烯。初步的机理研究表明，π-烯丙基金属和金属氢化物物质分别作为两个转化中的关键中间体。

  DOI：

  10.1021/acs.orglett.4c01668
• 作为产物：
  描述：

  顺式-2,4,5-三甲氧基-1-丙烯基苯 在 potassium permanganate 、 碳酸氢钠 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1-phenyl-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structure–activity relationship

  摘要：

  2,4,5-Trimethoxy chalcones and analogues were synthesized from asaronaldehyde derived from beta-asarone. These novel compounds when tested against three human tumour cell lines (MCF-7, SW-982 and HeLa) using MTT assay, revealed that chalcones possessing electron donor groups in para position to carbonyl moiety of phenyl ring A, showed better inhibitory activity (2, 3, 4, 6, 7, 10, 17). When evaluated for antioxidant activities, compound 15 exhibited better free radical scavenging property in DPPH assay while compounds 2, 3, 5, 7, 9, 10, 11, 16, and 18 showed significant NO scavenging activity. All compounds exhibited very good phenyl hydrazine induced haemolysis of erythrocytes in phenylhydrazine assay. Structure activity relationship (SAR) study using in-silico analysis matched well with in-vitro tumour cell inhibitory activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.018

文献信息

• C3 amino-substituted chalcone derivative with selective adenosine rA1 receptor affinity in the micromolar range
  作者：Helena D. Janse van Rensburg、Lesetja J. Legoabe、Gisella Terre’Blanche

  DOI：10.1007/s11696-020-01414-9

  日期：2021.4

  respectively, against rat (r) A1 and A2A ARs. The chalcone derivatives 24, 29, 37 and 38 possessed selective A1 affinity below 10 µM, and thus, are the most active compounds of the present series; compound 38 was the most potent selective A1 AR antagonist (K i (r) = 1.6 µM). The structure-affinity relationships (SAR) revealed that the NH2-group at position C3 of ring A of the chalcone scaffold played a key role

  摘要 为了鉴定基于查耳酮支架的新型腺苷受体 (AR) 配体，本文对 33 种查耳酮（15-36 和 37-41）以及结构相关化合物（42-47）进行了合成、表征以及体外和计算机评估。报道称。这些化合物通过放射性配体结合和 GTP 位移测定进行表征，以确定分别针对大鼠 (r) A1 和 A2A AR 的结合亲和力的程度和类型。查尔酮衍生物24、29、37和38具有低于10μM的选择性A1亲和力，因此是本系列中最活跃的化合物；化合物 38 是最有效的选择性 A1 AR 拮抗剂（K i (r) = 1.6 µM）。结构亲和关系（SAR）表明，查耳酮支架的A环C3位上的NH2基团在亲和力中起着关键作用，而且亚苄基环B上的C3'位上的Br原子也起着关键作用。通过计算机评估，新型 C3 氨基取代的查尔酮衍生物 38（包含 α,β-不饱和羰基系统并易于进行结构修饰）可能成为未来药物发现中的合成子。图摘要在亚苄基环
• Synthesis, Characterization and Antimicrobial Activities of Chalcones and Their Post Transformation to Pyrazole Derivatives
  作者：D. Ramyashree、K.R. Raghavendra、A. Dileep Kumar、C.B. Vagish、K. Ajay Kumar

  DOI：10.14233/ajchem.2017.20561

  日期：——

  An efficient procedure for the synthesis of trisubstituted pyrazoles was developed. Claisen-Schmidt condensation of 2,4,5-trimethoxybenzaldehyde and substituted acetophenone in the presence of aqueous alkaline bases produced chalcones. The cyclocondensation reaction of chalcones and phenyl hydrazine hydrochloride catalyzed by an acid produced trisubstituted pyrazolines in good yields. The synthesized new compounds were characterized by spectral studies and elemental analysis and some of the intermediate chalcones by single crystal X-ray diffraction studies. The compounds were screened in vitro for their antimicrobial susceptibilities against different bacteria and fungi species.

  开发了一种合成三取代吡唑的高效工艺。在含水碱性条件下，2,4,5-三甲氧基苯甲醛与取代苯乙酮进行克莱森-施密特缩合反应，生成查耳酮。在酸催化下，查耳酮与苯肼盐酸盐发生环化缩合反应，以良好产率生成三取代吡唑啉。通过光谱研究和元素分析对合成的新化合物进行了表征，部分中间体查耳酮通过单晶X射线衍射研究进行了鉴定。对这些化合物进行了体外抗菌活性筛选，测试了它们对不同细菌和真菌种类的抗菌敏感性。
• Inhibition of Caco-2 and MCF-7 cancer cells using chalcones: synthesis, biological evaluation and computational study
  作者：Marco Mellado、Mauricio Reyna-Jeldes、Caroline Weinstein-Oppenheimer、Claudio Coddou、Carlos Jara-Gutierrez、Joan Villena、Luis F. Aguilar

  DOI：10.1080/14786419.2021.1984465

  日期：2022.9.2

  development of novel anticancer agents derived from natural sources, like chalcone derivatives. For this investigation, twenty-three chalcones (4a-w) were synthesized and evaluated as antiproliferative agents against MCF-7 and Caco-2 cells, finding three and two compounds with similar or higher antiproliferative activity than daunorubicin, while only two chalcones showed better selectivity indexes than

  摘要 癌症是全球第二大死亡原因，其中乳腺癌和结肠癌是最常见的类型。传统的治疗策略有几个副作用，这些副作用激发了从天然来源（如查尔酮衍生物）中提取的新型抗癌剂的开发。在这项研究中，合成了 23 种查尔酮 ( 4a-w )，并对其作为抗 MCF-7 和 Caco-2 细胞的抗增殖剂进行了评估，发现三种和两种化合物具有与柔红霉素相似或更高的抗增殖活性，而只有两种查尔酮表现出更好的抗增殖活性在 MCF-7 上的选择性指数高于柔红霉素。根据这些结果，我们开发了性能良好的 QSAR 模型 (r > 0.850, q 2>0.650），发现了几个可以改变查尔酮活性和选择性的结构特征。根据这些模型，查尔酮4w和4t分别对 Caco-2 和 MCF-7 具有高效力和选择性，这使得它们成为开发 ROS 非依赖性促凋亡剂的潜在候选药物。
• Methoxychalcones: Effect of Methoxyl Group on the Antifungal, Antibacterial and Antiproliferative Activities
  作者：Beatriz C. Marques、Mariana B. Santos、Daiane B. Anselmo、Diego A. Monteiro、Eleni Gomes、Marilia F.C. Saiki、Paula Rahal、Pedro L. Rosalen、Janaina C.O. Sardi、Luis O. Regasini

  DOI：10.2174/1573406415666190724145158

  日期：2020.11.6

  general, chalcones of series I are the most potent antifungal, antibacterial and antiproliferative agents. 2',4',5'-Trimethoxychalcone (11) demonstrated potent antifungal activity against Candida krusei (MIC = 3.9 µg/mL), eight times more potent than fluconazole (reference antifungal drug). 3'-Methoxychalcone (6) displayed anti-Pseudomonas activity (MIC = 7.8 µg/mL). 2',5'-Dimethoxychalcone (9) displayed

  背景技术被甲氧基取代的查耳酮具有广泛的生物活性，包括抗真菌，抗菌和抗增殖作用。然而，尚未描述关于该取代基在查耳酮骨架上的相关性的明确和明确的研究。目的这项工作的目的是评估两个系列的十七种合成的区域异构甲氧基查耳酮的抑菌，抗真菌和抗增殖活性。系列I和II由分别被环A（5-12）和B（13-21）上的甲氧基取代的查耳酮构成。此外，甲氧基查耳酮的文库已提交计算机模拟药物和药代动力学性质的预测。方法合成甲氧基查耳酮，并通过NMR光谱数据分析确定其结构。对五种念珠菌，两种革兰氏阴性菌和五种革兰氏阳性菌进行了抗菌活性评估。对于抗增殖活性，针对四种人类致瘤细胞系以及人类非致瘤性角质形成细胞评估了甲氧基查耳酮。使用Molinspiration和PreADMET工具包可预测药物相似性和药代动力学特性。结果通常，系列I的查耳酮是最有效的抗真菌，抗菌和抗增殖剂。2'，4'，5'-三甲氧基查尔酮（11）对克鲁斯假丝酵母具有有效的抗真菌活性（MIC
• Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative Structure–Activity Relationship Models
  作者：Marco Mellado、Alejandro Madrid、Mauricio Reyna、Caroline Weinstein-Oppenheimer、Jaime Mella、Cristian O. Salas、Elizabeth Sánchez、Mauricio Cuellar

  DOI：10.1007/s00044-018-2245-2

  日期：2018.12

  Chalcones are a group of molecules with a broad spectrum of biological activities, being especially appealing for their antiproliferative effects on several cancer cell lines. For this reason, we synthesized 23 chalcones with good to excellent yields and assessed their effect on the viability of the SH-SY5Y neuroblastoma cell line and on primary human fibroblasts. The results indicated that 18 of these compounds were more active than 5-fluorouracil in the cancer cell line and one of them was more selective than this reference drug. To identify structural features related to the antiproliferative activity of these compounds, as well as, the selectivity on the cancer cell line, a 2D-QSAR analysis was performed. The QSAR model (q(2)=0.803; r(2)=0.836) showed that lipophilicity (CLogP) is the most important factor to increase their cytotoxicity on the cancer cell line. On the other hand, the selectivity QSAR model (q(2)=0.917; r(2)=0.916) showed that changes in the Mulliken's charge of the carbonyl group and at the C4' position in the chalcone core can increase the selectivity for SH-SY5Y cell line compared to normal fibroblasts.