(E)-3-(3,4-dichlorophenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one | 1352993-60-2

• 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-(3,4-dichlorophenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
• 英文别名: (2E)-3-(3,4-dichlorophenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
• CAS: 1352993-60-2
• 化学式: C₁₉H₁₂Cl₂O₂
• 分子量: 343.209
• InChiKey: PVJIQEOVQSCJKX-UXBLZVDNSA-N

物化性质

• 沸点：
  548.7±50.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙酰基-1-萘酚 、 3,4-二氯苯甲醛 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以64%的产率得到(E)-3-(3,4-dichlorophenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.10.074

文献信息

• Prostaglandin reductase inhibitors
  申请人：Lin Rong-Hwa

  公开号：US20090124688A1

  公开（公告）日：2009-05-14

  A method of inhibiting 15-keto prostaglandin-Δ 13 -reductase 2 by contacting 15-keto prostaglandin-Δ 13 -reductase 2 with an aryl compound of Formula (I), (II), (III), or (IV) shown herein. Also disclosed are methods of treating peroxisome proliferators-activated receptor related diseases and lowering blood glucose levels by administering to a subject in need thereof an effective amount of such an aryl compound.

  本发明涉及一种通过将公式（I），（II），（III）或（IV）的芳基化合物与15-酮前列腺素-Δ13-还原酶2接触来抑制15-酮前列腺素-Δ13-还原酶2的方法。本发明还公开了通过向需要的受试者施用有效量的这种芳基化合物来治疗过氧化物酶体增殖物活化受体相关疾病和降低血糖水平的方法。
• [EN] PROSTAGLANDIN REDUCTASE INHIBITORS<br/>[FR] INHIBITEURS DE PROSTAGLANDINE RÉDUCTASES
  申请人：ABGENOMICS CORP

  公开号：WO2007082178A2

  公开（公告）日：2007-07-19

  [EN] A method of inhibiting 15-keto prostaglandin-?¹³-reductase 2 by contacting 15-keto prostaglandin-?¹³-reductase 2 with an aryl compound of Formula (I), (II), (III), or (IV) shown herein. Also disclosed are methods of treating peroxisome proliferators-activated receptor related diseases and lowering blood glucose levels by administering to a subject in need thereof an effective amount of such an aryl compound.
  [FR] Procédé d'inhibition de la 15-céto-prostaglandine-?¹³-réductase 2 par la mise en contact de la 15-céto-prostaglandine-?¹³-réductase 2 avec un composé aryle de formule (I), (II), (III) ou (IV) illustrée dans la présente invention. La présente invention concerne également des procédés de traitement de maladies liées au récepteur activé par des proliférateurs de peroxysome et d'abaissement des taux de glucose sanguin en administrant une quantité efficace de ce composé d'aryle à un sujet nécessitant un tel traitement.
• 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.