(2E)-3-(2,4,5-trimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)propenone | 73694-37-8

• 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: (2E)-3-(2,4,5-trimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)propenone
• 英文别名: (E)-3-(2,4,5-trimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
• CAS: 73694-37-8
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: MZCVWDYOKBENCN-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 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 (2E)-3-(2,4,5-trimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)propenone
  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

• ANTI-INVASIVE COMPOUNDS
  申请人：Universiteit Gent

  公开号：US20150011620A1

  公开（公告）日：2015-01-08

  The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.

  本发明涉及抗侵袭化合物领域，以及预测该类化合物抗侵袭活性的方法，以及它们在预防和/或治疗与不受欢迎的细胞侵袭相关的疾病中的用途；特别是，本发明涉及抗侵袭的类似香豆素化合物领域。
• Synthesis of Xanthohumol Analogues and Discovery of Potent Thioredoxin Reductase Inhibitor as Potential Anticancer Agent
  作者：Baoxin Zhang、Dongzhu Duan、Chunpo Ge、Juan Yao、Yaping Liu、Xinming Li、Jianguo Fang

  DOI：10.1021/jm5016507

  日期：2015.2.26

  The selenoprotein thioredoxin reductases (TrxRs) are attractive targets for anticancer drugs development. Xanthohumol (Xn), a naturally occurring polyphenol chalcone from hops, has received increasing attention because of its multiple pharmacological activities. We synthesized Xn and its 43 analogues and discovered that compound 13n displayed the highest cytotoxicity toward HeLa cells (IC50 = 1.4 mu M). Structure-activity relationship study indicates that the prenyl group is not necessary for cytotoxicity, and introducing electron-withdrawing group, especially on the meta-position, is favored. In addition, methylation of the phenoxyl groups generally improves the potency. Mechanistic study revealed that 13n selectively inhibits TrxR and induces reactive oxygen species and apoptosis in HeLa cells. Cells overexpressing TrxR are resistant to 13n insult, while knockdown of TrxR sensitizes cells to 13n treatment, highlighting the physiological significance of targeting TrxR by 13n. The clarification of the structural determinants for the potency would guide the design of novel potent molecules for future development.
• 4-Fluoro-3′,4′,5′-trimethoxychalcone as a new anti-invasive agent. From discovery to initial validation in an in vivo metastasis model
  作者：Bart I. Roman、Tine De Ryck、Atanas Patronov、Svetoslav H. Slavov、Barbara W.A. Vanhoecke、Alan R. Katritzky、Marc E. Bracke、Christian V. Stevens

  DOI：10.1016/j.ejmech.2015.06.029

  日期：2015.8

  Invasion and metastasis are responsible for 90% of cancer-related mortality. Herein, we report on our quest for novel, clinically relevant inhibitors of local invasion, based on a broad screen of natural products in a phenotypic assay. Starting from micromolar chalcone hits, a predictive QSAR model for diaryl propenones was developed, and synthetic analogues with a 100-fold increase in potency were obtained. Two nanomolar hits underwent efficacy validation and eADMET profiling; one compound was shown to increase the survival time in an artificial metastasis model in nude mice. Although the molecular mechanism(s) by which these substances mediate efficacy remain(s) unrevealed, we were able to eliminate the major targets commonly associated with antineoplastic chalcones. (C) 2015 Elsevier Masson SAS. All rights reserved.
• US9290427B2
  申请人：——

  公开号：US9290427B2

  公开（公告）日：2016-03-22
• [EN] ANTI-INVASIVE COMPOUNDS<br/>[FR] COMPOSÉS ANTI-INVASIFS
  申请人：UNIV GENT

  公开号：WO2013113722A1

  公开（公告）日：2013-08-08

  The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.