(E)-3-(2,3-dimethoxyphenyl)-1-phenylprop-2-en-1-one | 39060-01-0

• 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: (E)-3-(2,3-dimethoxyphenyl)-1-phenylprop-2-en-1-one
• 英文别名: 2,3-dimethoxy-trans-chalcone；2,3-Dimethoxy-trans-chalkon；(2E)-3-(2,3-Dimethoxyphenyl)-1-phenylprop-2-en-1-one
• CAS: 39060-01-0
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: MGTKFVPIOWZSND-VAWYXSNFSA-N

物化性质

• 沸点：
  198-199 °C(Press: 2 Torr)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,3-dimethoxyphenyl)-1-phenylprop-2-en-1-one 在 铂 作用下， 生成 3-(2,3-dimethoxy-phenyl)-1-phenyl-propan-1-one
  参考文献：
  名称：

  Esters of α-(2-Dialkylaminoethyl)-benzyl Alcohols

  摘要：

  DOI：

  10.1021/ja01154a104
• 作为产物：
  描述：

  苯乙酮 、 2,3-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以41%的产率得到(E)-3-(2,3-dimethoxyphenyl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents

  摘要：

  通过Claisen-Schmidt反应设计并合成了一些查耳酮类化合物，作为铁氧化还原蛋白和铁氧化还原蛋白-NADP+还原酶相互作用的抑制剂，以追求一种新的选择性抗疟药物。合成的化合物表现出对PfFd-PfFNR相互作用的抑制作用，抑制率在10.94%至50%之间。具有最强抑制活性的三种化合物分别为：(E)-1-(4-氨基苯基)-3-(4-甲氧基苯基)丙-2-烯-1-酮（50%），(E)-1-(4-氨基苯基)-3-(2,4-二甲氧基苯基)丙-2-烯-1-酮（38.16%），以及(E)-1-(4-氨基苯基)-3-(2,3-二甲氧基苯基)丙-2-烯-1-酮（31.58%）。从对接实验中我们确定，甲氧氨基查耳酮衍生物的氨基通过盐桥的静电相互作用在抑制活性中起着重要作用，并且它与FNR形成的复合物比与Fd形成的复合物更稳定、亲和力更好。

  DOI：

  10.3390/molecules191221473

文献信息

• 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
• In vitro antifungal evaluation and structure–activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall
  作者：Silvia N López、Marı́a V Castelli、Susana A Zacchino、José N Domı́nguez、Gricela Lobo、Jaime Charris-Charris、Juan C.G Cortés、Juan C Ribas、Cristina Devia、Ana M Rodrı́guez、Ricardo D Enriz

  DOI：10.1016/s0968-0896(01)00116-x

  日期：2001.8

  Here we report the synthesis, in vitro antifungal evaluation and SAR study of 41 chalcones and analogues. In addition, all active structures were tested for their capacity of inhibiting Saccharomyces cerevisiae beta (1,3)-glucan synthase and chitin synthase, enzymes that catalyze the synthesis of the major polymers of the fungal cell wall. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics
  作者：Thanh-Dao Tran、Tuong-Ha Do、Ngoc-Chau Tran、Trieu-Du Ngo、Thi-Ngoc-Phuong Huynh、Cat-Dong Tran、Khac-Minh Thai

  DOI：10.1016/j.bmcl.2012.05.112

  日期：2012.7

  A total of 30 chalcone analogues was synthesized via a base catalyzed Claisen Schmidt condensation and screened for their in vitro antibacterial activity against Methicillin-sensitive Staphylococcus aureus (MSSA) and Methicillin-resistant Staphylococcus aureus (MRSA) alone or in combination with non beta-lactam antibiotics namely ciprofloxacin, chloramphenicol, erythromycin, vancomycin, doxycycline and gentamicin. In the checkerboard technique, fractional inhibitory concentration indices (FICI) show that the following combinations like ciprofloxacin with 25 (4'-bromo-2-hydroxychalcone); doxycycline with 21 (4-hydroxychalcone); doxycycline with 25; and doxycycline with 4 (2',2-dihydroxychalcone) were synergistic against MRSA. In term SAR study, the relationship between chalcone structure and their antibacterial activity against S. aureus and synergy with tested antibiotics were discussed. Possible mechanisms for antibacterial activity of chalcones alone as well as the synergistic effect in combinations were proposed by molecular modeling studies, respectively. Combinations of chalcones with conventional antibiotics could be an effective alternative in the treatment of infection caused by MRSA. (C) 2012 Elsevier Ltd. All rights reserved.
• 2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis
  作者：Douglas G. Batt、Robin Goodman、David G. Jones、Janet S. Kerr、Lisa R. Mantegna、Candice McAllister、Robert C. Newton、Sherrill Nurnberg、Patricia K. Welch、Maryanne B. Covington

  DOI：10.1021/jm00062a016

  日期：1993.5

  A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1beta from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-muM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings beta to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.
• MOUSSA, H. H.;CHABAKA, L. M.;ZAKI, D., EGYPT. J. CHEM., 1983, 26, N 6, 469-477
  作者：MOUSSA, H. H.、CHABAKA, L. M.、ZAKI, D.

  DOI：——

  日期：——