4-acetoxy-2',4'-dimethoxychalcone | 876513-28-9

• 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: 4-acetoxy-2',4'-dimethoxychalcone
• 英文别名: 4-[3-(2,4-Dimethoxyphenyl)-3-oxoprop-1-en-1-yl]phenyl acetate；[4-[3-(2,4-dimethoxyphenyl)-3-oxoprop-1-enyl]phenyl] acetate
• CAS: 876513-28-9
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: XTFDWSGQZILIFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二甲氧基苯乙酮 在 吡啶 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 4-acetoxy-2',4'-dimethoxychalcone
  参考文献：
  名称：

  In vivo anti-diabetic activity of derivatives of isoliquiritigenin and liquiritigenin

  摘要：

  Isoliquiritigenin (ISL), a chalcone and liquiritigenin (LTG), a flavonoid found in licorice roots and several other plants. ISL displays antioxidant, anti-inflammatory, antitumor and hepatoprotective activities whereas LTG is an estrogenic compound, acts as an agonist selective for the beta-subtype of the oestrogen receptor. Both the phenolics were isolated from the rhizomes of Glycyrrhiza glabra. Five derivatives from ISL and four derivatives from LTG were synthesized. All the compounds were established by extensive spectroscopic analyses and screened through oral glucose tolerance test to gain preliminary information regarding the antihyperglycemic effect in normal Swiss albino male mice. ISL (1), ISL derivatives 3, 4, 5, 7 and LTG derivatives 9 and 10 showed significant blood glucose lowering effect. The structure-activity relationship indicated that the presence of ether and ester groups in ISL and LTG analogues are important for exhibiting the activity. Compounds 1,4 and 10 were selected for in vivo antidiabetic activity and found to be potential candidates for treatment of diabetes. It is the first report on antidiabetic activity of ISL derivative 4 and LTG derivative 10. (C) 2013 Elsevier GmbH. All rights reserved.

  DOI：

  10.1016/j.phymed.2013.10.015

文献信息

• In vivo anti-diabetic activity of derivatives of isoliquiritigenin and liquiritigenin
  作者：Rashmi Gaur、Kuldeep Singh Yadav、Ram Kishor Verma、Narayan Prasad Yadav、Rajendra Singh Bhakuni

  DOI：10.1016/j.phymed.2013.10.015

  日期：2014.3

  Isoliquiritigenin (ISL), a chalcone and liquiritigenin (LTG), a flavonoid found in licorice roots and several other plants. ISL displays antioxidant, anti-inflammatory, antitumor and hepatoprotective activities whereas LTG is an estrogenic compound, acts as an agonist selective for the beta-subtype of the oestrogen receptor. Both the phenolics were isolated from the rhizomes of Glycyrrhiza glabra. Five derivatives from ISL and four derivatives from LTG were synthesized. All the compounds were established by extensive spectroscopic analyses and screened through oral glucose tolerance test to gain preliminary information regarding the antihyperglycemic effect in normal Swiss albino male mice. ISL (1), ISL derivatives 3, 4, 5, 7 and LTG derivatives 9 and 10 showed significant blood glucose lowering effect. The structure-activity relationship indicated that the presence of ether and ester groups in ISL and LTG analogues are important for exhibiting the activity. Compounds 1,4 and 10 were selected for in vivo antidiabetic activity and found to be potential candidates for treatment of diabetes. It is the first report on antidiabetic activity of ISL derivative 4 and LTG derivative 10. (C) 2013 Elsevier GmbH. All rights reserved.
• Synthesis, antitubercular activity, and molecular modeling studies of analogues of isoliquiritigenin and liquiritigenin, bioactive components from Glycyrrhiza glabra
  作者：Rashmi Gaur、Jay Prakash Thakur、Dharmendra K. Yadav、Deepak Singh Kapkoti、Ram Kishor Verma、Namita Gupta、Feroz Khan、Dharmendra Saikia、Rajendra Singh Bhakuni

  DOI：10.1007/s00044-015-1401-1

  日期：2015.9

  Isoliquiritigenin (ISL, 1) and liquiritigenin (LTG, 2) were isolated from the rhizomes of Glycyrrhiza glabra. In an attempt to develop potent and selective antituberculosis agents, a series of ISL analogues were synthesized mainly via acid- and base-catalyzed Claisen-Schmidt condensation reaction for their antitubercular activity. Compared to ISL (MIC = 25 mu g/mL), analogues 5, 8, and 10 showed similar antitubercular activity, but, interestingly, 6, 7, and 15 exhibited twofold higher activity (MIC = 12.5 mu g/mL) over ISL, against Mycobacterium tuberculosis. Among the LTG derivatives, LTG 4'-acetate and LTG-oxime were found to be as active (MIC = 25 mu g/mL) as LTG. It is the first report on antimycobacterial activity of these ISL- and LTG-based derivatives. Molecular docking and in silico ADME studies revealed that compounds 6, 7, and 15 are potent inhibitors of M. tuberculosis H(37)Rv alanine dehydrogenase and showed compliance with standard parameters of drug likeness.