LIT-927游离 | 2172879-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: LIT-927游离
• 英文名称: 4-(4-chlorophenyl)-6-(4-hydroxy-3-methoxyphenyl)pyrimidin-2(1H)-one
• 英文别名: 4-(4-Chlorophenyl)-6-(4-hydroxy-3-methoxyphenyl)pyrimidin-2(1H)-one；6-(4-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-1H-pyrimidin-2-one
• CAS: 2172879-52-4
• 化学式: C₁₇H₁₃ClN₂O₃
• 分子量: 328.755
• InChiKey: BYYRNPIGDRRGLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯苯乙酮 在 盐酸 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 生成 LIT-927游离
  参考文献：
  名称：

  [EN] PYRIMIDINONE DERIVATIVES AND USES THEREOF TO NEUTRALIZE THE BIOLOGICAL ACTIVITY OF CHEMOKINES
  [FR] DÉRIVÉS DE PYRIMIDINONE ET LEURS UTILISATIONS POUR NEUTRALISER L'ACTIVITÉ BIOLOGIQUE DES CHIMIOKINES

  摘要：

  本发明的一个主题是具有通式（I）的化合物，其药学上可接受的盐或其互变异构体，其中A、B3、B4、B5、Y、X、B1和B2如权利要求1至10中的任一所定义。本发明的另一个主题是上述定义的化合物作为药物的用途，特别用于预防和/或治疗炎症和炎症性疾病、免疫和自身免疫疾病、与疼痛有关的疾病、遗传疾病和/或癌症。

  公开号：

  WO2018011376A1

文献信息

• Pyrimidinone derivatives and uses thereof to neutralize the biological activity of chemokines
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US11046657B2

  公开（公告）日：2021-06-29

  A subject of the present invention is a compound having the general formula (I): a pharmaceutically acceptable salt thereof or a tautomeric form thereof, wherein A, B3, B4, B5, Y, X, B1 and B2 are as defined in any one of claims 1 to 10. Another subject of the invention is the compound as defined above for use as a medicament, in particular for preventing and/or treating inflammation and inflammatory diseases, immune and auto-immune diseases, pain related diseases, genetic diseases and/or cancer.

  本发明的一个主题是具有通式 (I) 的化合物： 其药学上可接受的盐或其同分异构体、 其中 A、B3、B4、B5、Y、X、B1 和 B2 如权利要求 1 至 10 中任一项所定义。 本发明的另一个主题是上文定义的化合物，可用作药物，特别是用于预防和/或治疗炎症和炎症性疾病、免疫和自身免疫性疾病、疼痛相关疾病、遗传性疾病和/或癌症。
• 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.
• Pyrimidinone Derivatives and Uses Thereof to Neutralize the Biological Activity of Chemokines
  申请人：Centre National de la Recherche Scientifique (CNRS

  公开号：US20200181093A1

  公开（公告）日：2020-06-11

  A subject of the present invention is a compound having the general formula (I): a pharmaceutically acceptable salt thereof or a tautomeric form thereof, wherein A, B 3 , B 4 , B 5 , Y, X, B 1 and B 2 are as defined in any one of claims 1 to 10. Another subject of the invention is the compound as defined above for use as a medicament, in particular for preventing and/or treating inflammation and inflammatory diseases, immune and auto-immune diseases, pain related diseases, genetic diseases and/or cancer.
• [EN] PYRIMIDINONE DERIVATIVES AND USES THEREOF TO NEUTRALIZE THE BIOLOGICAL ACTIVITY OF CHEMOKINES<br/>[FR] DÉRIVÉS DE PYRIMIDINONE ET LEURS UTILISATIONS POUR NEUTRALISER L'ACTIVITÉ BIOLOGIQUE DES CHIMIOKINES
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENT - CNRS -

  公开号：WO2018011376A1

  公开（公告）日：2018-01-18

  A subject of the present invention is a compound having the general formula (I) a pharmaceutically acceptable salt thereof or a tautomeric form thereof, wherein A, B3, B4, B5, Y, X, B1 and B2 are as defined in any one of claims 1 to 10. Another subject of the invention is the compound as defined above for use as a medicament, in particular for preventing and/or treating inflammation and inflammatory diseases, immune and auto-immune diseases, pain related diseases, genetic diseases and/or cancer.

  本发明的一个主题是具有通式（I）的化合物，其药学上可接受的盐或其互变异构体，其中A、B3、B4、B5、Y、X、B1和B2如权利要求1至10中的任一所定义。本发明的另一个主题是上述定义的化合物作为药物的用途，特别用于预防和/或治疗炎症和炎症性疾病、免疫和自身免疫疾病、与疼痛有关的疾病、遗传疾病和/或癌症。