(E)-3-(3-pyridyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-(3-pyridyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(pyridin-3-yl)-1-(2,3₉4-trimethoxyphenyl)prop-2-en-1-one；DMU718；3-(Pyridin-3-yl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one；(E)-3-pyridin-3-yl-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: QNSVIKWLSFHHDS-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-pyridyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以8.7 %的产率得到(E)-3-(pyridin-3-yl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  [EN] ESTROGENIC COMPOUNDS AND METHODS OF USE
  [FR] COMPOSÉS ŒSTROGÉNIQUES ET MÉTHODES D'UTILISATION

  摘要：

  Estrogenic compounds, compositions and method are presented. The novel estrogenic compounds comprise novel chalcone derivatives and analogs that have little or no measurable estrogen (estradiol, E2) activity but potentiate E2 activity without binding an estrogen receptor (ER). The novel compositions comprise one or more of the novel estrogenic compounds, and may optionally comprise one or more excipients. The one or more excipients may be pharmaceutically acceptable. The one or more excipients may comprise at least one compound that does not occur in nature with estrogenic compounds. The method comprises administering a pharmaceutical composition comprising an estrogenic compound described herein to a patient in need of treatment with an estrogenic compound or pharmaceutical composition.

  公开号：

  WO2024026034A1
• 作为产物：
  描述：

  3-吡啶甲醛 、 2',3',4'-三甲氧基苯乙酮 在 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以51%的产率得到(E)-3-(3-pyridyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines

  摘要：

  The structure of alpha-napthoflavone (ANF), a potent inhibitor of CYP1A1 and CYP1B1, mimics the structure of chalcones. Two potent CYP1B1 inhibitors 7k (DMU2105) and 6j (DMU2139) have been identified from two series of synthetic pyridylchalcones. They inhibit human CYP1B1 enzyme bound to yeast-derived microsomes (Sacchrosomes((TM))) with IC50 values of 10 and 9 nM, respectively, and show a very high level of selectivity towards CYP1B1 with respect to the IC50 values obtained with CYP1A1, CYP1A2, CYP3A4, CYP2D6, CYP2C9 and CYP2C19 Sacchrosomes((TM)). Both compounds also potently inhibit CYP1B1 expressed within 'live' recombinant yeast and human HEK293 kidney cells with IC50 values of 63, 65, and 4, 4 nM, respectively. Furthermore, the synthesized pyridylchalcones possess better solubility and lipophilicity values than ANF. Both compounds overcome cisplatine-resistance in HEK293 and A2780 cells which results from CYP1B1 overexpression. These potent cell-permeable and water-soluble CYP1B1 inhibitors are likely to have useful roles in the treatment of cancer, glaucoma, ischemia and obesity. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.016

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：UNIV MONTFORT

  公开号：WO2015166043A1

  公开（公告）日：2015-11-05

  The invention relates to a compound of formula (I) for use in the prevention and/or treatment of cancer, wherein rings A and B are independently an optionally substituted aryl or an optionally substituted heteroaryl. The compounds are particularly provided for the prevention and/or treatment of hormone- induced cancers, such as breast, ovarian, uterine, endometrial and prostate cancer.
• Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines
  作者：Neill J. Horley、Kenneth J.M. Beresford、Tarun Chawla、Glen J.P. McCann、Ketan C. Ruparelia、Linda Gatchie、Vinay R. Sonawane、Ibidapo S. Williams、Hoon L. Tan、Prashant Joshi、Sonali S. Bharate、Vikas Kumar、Sandip B. Bharate、Bhabatosh Chaudhuri

  DOI：10.1016/j.ejmech.2017.02.016

  日期：2017.3

  The structure of alpha-napthoflavone (ANF), a potent inhibitor of CYP1A1 and CYP1B1, mimics the structure of chalcones. Two potent CYP1B1 inhibitors 7k (DMU2105) and 6j (DMU2139) have been identified from two series of synthetic pyridylchalcones. They inhibit human CYP1B1 enzyme bound to yeast-derived microsomes (Sacchrosomes((TM))) with IC50 values of 10 and 9 nM, respectively, and show a very high level of selectivity towards CYP1B1 with respect to the IC50 values obtained with CYP1A1, CYP1A2, CYP3A4, CYP2D6, CYP2C9 and CYP2C19 Sacchrosomes((TM)). Both compounds also potently inhibit CYP1B1 expressed within 'live' recombinant yeast and human HEK293 kidney cells with IC50 values of 63, 65, and 4, 4 nM, respectively. Furthermore, the synthesized pyridylchalcones possess better solubility and lipophilicity values than ANF. Both compounds overcome cisplatine-resistance in HEK293 and A2780 cells which results from CYP1B1 overexpression. These potent cell-permeable and water-soluble CYP1B1 inhibitors are likely to have useful roles in the treatment of cancer, glaucoma, ischemia and obesity. (C) 2017 Elsevier Masson SAS. All rights reserved.
• [EN] ESTROGENIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS ŒSTROGÉNIQUES ET MÉTHODES D'UTILISATION
  申请人：[en]IATERION, INC.

  公开号：WO2024026034A1

  公开（公告）日：2024-02-01

  Estrogenic compounds, compositions and method are presented. The novel estrogenic compounds comprise novel chalcone derivatives and analogs that have little or no measurable estrogen (estradiol, E2) activity but potentiate E2 activity without binding an estrogen receptor (ER). The novel compositions comprise one or more of the novel estrogenic compounds, and may optionally comprise one or more excipients. The one or more excipients may be pharmaceutically acceptable. The one or more excipients may comprise at least one compound that does not occur in nature with estrogenic compounds. The method comprises administering a pharmaceutical composition comprising an estrogenic compound described herein to a patient in need of treatment with an estrogenic compound or pharmaceutical composition.