(E)-3-(2-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one

• 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-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 2-chloro-2'-hydroxy-4'-methoxy-trans-chalcone；2-chloro-2'-hydroxy-4'-methoxy-chalcone；2-Chlor-2'-hydroxy-4'-methoxy-trans-chalkon；2-Chlor-2'-hydroxy-4'-methoxy-chalkon；(2E)-3-(2-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: ODHIKTBXCYVAFQ-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one 生成 2'-acetoxy-2-chloro-4'-methoxy-trans-chalcone
  参考文献：
  名称：

  Vallotton, 1923, vol. 3, p. 145,147

  摘要：

  DOI：
• 作为产物：
  描述：

  丹皮酚 、 2-氯苯甲醛 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以48%的产率得到(E)-3-(2-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Antimitotic and Antiproliferative Activities of Chalcones: Forward Structure–Activity Relationship

  摘要：

  A series of 59 chalcones was prepared and evaluated for the antimitotic effect against K562 leukemia cells. The most active chalcones were evaluated for their antiproliferative activity against a panel of I I human and murine cell cancer lines. We found that three chalcones were of great interest as potential antimitotic drugs. In vivo safety studies conducted on one of the most active chalcones revealed that the compound was safe, allowing further in vivo antitumor evaluation.

  DOI：

  10.1021/jm0708331

文献信息

• Antimitotic and Antiproliferative Activities of Chalcones: Forward Structure–Activity Relationship
  作者：Ahcène Boumendjel、Julien Boccard、Pierre-Alain Carrupt、Edwige Nicolle、Madeleine Blanc、Annabelle Geze、Luc Choisnard、Denis Wouessidjewe、Eva-Laure Matera、Charles Dumontet

  DOI：10.1021/jm0708331

  日期：2008.4.1

  A series of 59 chalcones was prepared and evaluated for the antimitotic effect against K562 leukemia cells. The most active chalcones were evaluated for their antiproliferative activity against a panel of I I human and murine cell cancer lines. We found that three chalcones were of great interest as potential antimitotic drugs. In vivo safety studies conducted on one of the most active chalcones revealed that the compound was safe, allowing further in vivo antitumor evaluation.
• Roethlisberger, Helvetica Chimica Acta, 1925, vol. 8, p. 116
  作者：Roethlisberger

  DOI：——

  日期：——
• Vallotton, 1923, vol. 3, p. 145,146
  作者：Vallotton

  DOI：——

  日期：——
• Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein
  作者：Kapil Juvale、Veronika F.S. Pape、Michael Wiese

  DOI：10.1016/j.bmc.2011.10.074

  日期：2012.1

  Breast cancer resistance protein (BCRP/ABCG2) belongs to the ATP binding cassette family of transport proteins. BCRP has been found to confer multidrug resistance in cancer cells. A strategy to overcome resistance due to BCRP overexpression is the investigation of potent and specific BCRP inhibitors. The aim of the current study was to investigate different multi-substituted chalcones for their BCRP inhibition. We synthesized chalcones and benzochalcones with different substituents (viz. OH, OCH3, Cl) on ring A and B of the chalcone structure. All synthesized compounds were tested by Hoechst 33342 accumulation assay to determine inhibitory activity in MCF-7 MX and MDCK cells expressing BCRP. The compounds were also screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity in the calcein AM accumulation assay and were found to be selective towards inhibition of BCRP. Substituents at position 20 and 40 on chalcone ring A were found to be essential for activity; additionally there was a great influence of substituents on ring B. Presence of 3,4-dimethoxy substitution on ring B was found to be optimal, while presence of 2- and 4-chloro substitution also showed a positive effect on BCRP inhibition. (C) 2011 Elsevier Ltd. All rights reserved.
• Vallotton, <hi>1923</hi>, vol. 3, p. 145,147
  作者：Vallotton

  DOI：——

  日期：——