(E)-1-(4-chlorophenyl)-3-(3-ethoxy-4-hydroxyphenyl)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)-1-(4-chlorophenyl)-3-(3-ethoxy-4-hydroxyphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₅ClO₃
• 分子量: 302.757
• InChiKey: HOKXZSSLXZDGLC-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  丁二酸酐 、 (E)-1-(4-chlorophenyl)-3-(3-ethoxy-4-hydroxyphenyl)prop-2-en-1-one 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 以342 mg的产率得到4-(3-(4-chlorophenyl)-5-(3-ethoxy-4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-oxobutanoic acid
  参考文献：
  名称：

  METHANOGEN INHIBITORS

  摘要：

  The present invention relates to a new class of methanogen inhibitors for ruminants. The invention also extends to the use of such compounds in ruminants to reduce methane production in the rumen and/or to enhance productivity in the ruminant.

  公开号：

  WO2024039250A1
• 作为产物：
  描述：

  乙基香兰素 、 对氯苯乙酮 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到(E)-1-(4-chlorophenyl)-3-(3-ethoxy-4-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Discovery of a Locally and Orally Active CXCL12 Neutraligand (LIT-927) with Anti-inflammatory Effect in a Murine Model of Allergic Airway Hypereosinophilia

  摘要：

  We previously reported Chalcone-4 (1) that binds the chemokine CXCL12, not its cognate receptors CXCR4 or CXCR7, and neutralizes its biological activity. However, this neutraligand suffers from limitations such as poor chemical stability, solubility, and oral activity. Herein, we report on the discovery of pyrimidinone 57 (LIT-927), a novel neutraligand of CXCL12 which displays a higher solubility than 1 and is no longer a Michael acceptor. While both 1 and 57 reduce eosinophil recruitment in a murine model of allergic airway hypereosinophilia, 57 is the only one to display inhibitory activity following oral administration. Thereby, we here describe 57 as the first orally active CXCL12 neutraligand with anti-inflammatory properties. Combined with a high binding selectivity for CXCL12 over other chemokines, 57 represents a powerful pharmacological tool to investigate CXCL12 physiology in vivo and to explore the activity of chemokine neutralization in inflammatory and related diseases.

  DOI：

  10.1021/acs.jmedchem.8b00657

文献信息

• Discovery of a Locally and Orally Active CXCL12 Neutraligand (LIT-927) with Anti-inflammatory Effect in a Murine Model of Allergic Airway Hypereosinophilia
  作者：Pierre Regenass、Dayana Abboud、François Daubeuf、Christine Lehalle、Patrick Gizzi、Stéphanie Riché、Muriel Hachet-Haas、François Rohmer、Vincent Gasparik、Damien Boeglin、Jacques Haiech、Tim Knehans、Didier Rognan、Denis Heissler、Claire Marsol、Pascal Villa、Jean-Luc Galzi、Marcel Hibert、Nelly Frossard、Dominique Bonnet

  DOI：10.1021/acs.jmedchem.8b00657

  日期：2018.9.13

  We previously reported Chalcone-4 (1) that binds the chemokine CXCL12, not its cognate receptors CXCR4 or CXCR7, and neutralizes its biological activity. However, this neutraligand suffers from limitations such as poor chemical stability, solubility, and oral activity. Herein, we report on the discovery of pyrimidinone 57 (LIT-927), a novel neutraligand of CXCL12 which displays a higher solubility than 1 and is no longer a Michael acceptor. While both 1 and 57 reduce eosinophil recruitment in a murine model of allergic airway hypereosinophilia, 57 is the only one to display inhibitory activity following oral administration. Thereby, we here describe 57 as the first orally active CXCL12 neutraligand with anti-inflammatory properties. Combined with a high binding selectivity for CXCL12 over other chemokines, 57 represents a powerful pharmacological tool to investigate CXCL12 physiology in vivo and to explore the activity of chemokine neutralization in inflammatory and related diseases.
• METHANOGEN INHIBITORS
  申请人：[en]PASTORAL GREENHOUSE GAS RESEARCH LIMITED

  公开号：WO2024039250A1

  公开（公告）日：2024-02-22

  The present invention relates to a new class of methanogen inhibitors for ruminants. The invention also extends to the use of such compounds in ruminants to reduce methane production in the rumen and/or to enhance productivity in the ruminant.