(2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one | 61777-22-8

• 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)-1-(2,4,6-trimethoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
• 英文别名: (E)-3-(4-hydroxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one；(E)-4-hydroxy-2',4',6'-trimethoxychalcone；4-hydroxy-2',4',6'-trimethoxy-chalcone；4-Hydroxy-2',4',6'-trimethoxy-chalkon；4-Hydroxy-2',4',6'-trimethoxychalcone
• CAS: 61777-22-8
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: ZWNLSRDFHQCTQW-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以11%的产率得到柚皮素查尔酮
  参考文献：
  名称：

  Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

  摘要：

  Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as aglucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards aglucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good a-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 mu M concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line). (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.007
• 作为产物：
  描述：

  2,4,6-三甲氧基苯乙酮 、 对羟基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以79%的产率得到(2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Mechanisms of action and structure-activity relationships of cytotoxic flavokawain derivatives

  摘要：

  22 Flavokawain derivatives (FKd) were obtained by one step syntheses in order to conduct a SAR study to understand the structural requirements for optimum and selective cytotoxicity. FKd and natural flavokawains A and B found into kava, a South Pacific traditional beverage, were evaluated against nine cancer and one healthy cell lines. The targeted cell cycle phases as well as the effects on the induction of apoptosis and cell cycle protein levels were investigated. Therapeutic improvements (more activity and selectivity) were achieved with FKd compared to natural flavokawains and notably with the 2',3,4',6'-tetramethoxychalcone (FKd 19). FKd induced a Gl/S arrest on p53 wild-type cells and an M arrest on p53 mutant-type, via the up-regulation of p21 and cyclin B1 proteins, followed by apoptosis. Moreover, FKd exhibited a 24 h-effect on Akt/mTor normal cells versus a 48 h-effect on Akt/mTor up-regulated cells. The SAR study resulted in the conclusion that trimethoxy A-ring allowed the best compromise between cytotoxicity and selectivity, as well as the substitution of the meta position on the B-ring and the use of halogens substituents. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.01.049

文献信息

• [EN] DRUG FOR ANTAGONIZING REPLICATION OF PORCINE REPRODUCTIVE AND RESPIRATORY SYNDROME VIRUS AND APPLICATION THEREOF<br/>[FR] MÉDICAMENT POUR ANTAGONISER LA RÉPLICATION DU VIRUS DU SYNDROME RESPIRATOIRE ET REPRODUCTEUR PORCIN ET SON APPLICATION<br/>[ZH] 一种拮抗猪繁殖与呼吸综合征病毒复制的药物及其应用
  申请人：UNIV NANJING AGRICULTURAL

  公开号：WO2021068533A1

  公开（公告）日：2021-04-15

  一种拮抗猪繁殖与呼吸综合征病毒复制的药物及其应用，采用病毒感染试验，从386种植物来源的天然药物库中首次发现一种PRRSV拮抗药物—黄腐酚。黄腐酚在Marc-145和PAM细胞上均可有效抑制PRRSV复制。人工合成5种不同分子结构的黄腐酚衍生物，发现衍生物Xn-4体外抑制病毒复制作用最强。仔猪人工感染和药物治疗试验结果显示，Xn-4能够有效地抑制PRRSV病毒血症，减轻感染猪临床症状，显著降低肺部炎症和病理损伤。
• 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.
• Mosimann; Tambor, Chemische Berichte, 1916, vol. 49, p. 1701
  作者：Mosimann、Tambor

  DOI：——

  日期：——
• USE OF CHALCONES FOR THE TREATMENT OF VIRAL DISORDERS
  申请人：Johnson and Johnson Consumer Companies, Inc.

  公开号：EP1888174B1

  公开（公告）日：2012-02-22
• Use of chalcones for the treatment of viral disorders
  申请人：Boddupalli Sekhar

  公开号：US20060270614A1

  公开（公告）日：2006-11-30

  The present invention relates to chalcone derivatives and compositions containing such derivatives useful in the treatment of viral disorders, including but not limited to the treatment of viral lesions resulting from viruses such as Herpes Simplex virus.