5-(4-氯苯基)-6-羟基-4(1H)-吡啶酮 | 3979-80-4

• 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: 5-(4-氯苯基)-6-羟基-4(1H)-吡啶酮
• 英文名称: 5-(4-chlorophenyl)pyrimidine-4,6-diol
• 英文别名: 5-(4-chloro-phenyl)-1H-pyrimidine-4,6-dione；5-(4-chlorophenyl)-pyrimidine-4,6-diol；4,6-Dihydroxy-5-(4-chlorphenyl)-pyrimidin, 4,6-Dihydroxy-5-(p-chlor-phenyl)-pyrimidin；4,6-Dihydroxy-5-(4-chlorphenyl)-pyrimidin；5-(4-chlorophenyl)-4-hydroxy-1H-pyrimidin-6-one
• CAS: 3979-80-4
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: AZCIUNXJXVOJGZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-氯苯基)-6-羟基-4(1H)-吡啶酮 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 氢碘酸 、 三乙胺 、 sodium iodide 、 三氯氧磷 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 15.0h， 生成 4-{5-[5-(4-chlorophenyl)-6-iodopyrimidin-4-ylethynyl]pyrimidin-2-yl}morpholine
  参考文献：
  名称：

  4-Amino-5-aryl-6-arylethynylpyrimidines: Structure–activity relationships of non-nucleoside adenosine kinase inhibitors

  摘要：

  A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-yipyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.029
• 作为产物：
  描述：

  对氯苯乙酸甲酯 在 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 51.0h， 生成 5-(4-氯苯基)-6-羟基-4(1H)-吡啶酮
  参考文献：
  名称：

  的发现ñ - [5-（4-溴苯基）-6- [2 - [（5-溴-2-嘧啶基）氧基]乙氧基] -4-嘧啶基] - ñ '-propylsulfamide（美西特田），一种口服活性，强效双重内皮素受体拮抗剂

  摘要：

  从波生坦（1）的结构开始，我们着手于一项药物化学程序，旨在鉴定具有高口服功效的新型有效的双重内皮素受体拮抗剂。这导致发现了一系列新的烷基磺酰胺取代的嘧啶。其中，化合物17（macitentan，ACT-064992）引起了人们的特别关注，因为它是对ET B受体具有显着亲和力的ET A的有效抑制剂，并且在高血压Dahl盐敏感性大鼠中显示出优异的药代动力学特性和高体内功效。化合物17成功完成了一项肺动脉高压的长期III期临床试验。

  DOI：

  10.1021/jm3009103

文献信息

• Arylalkane-sulfonamides having endothelin-antagonist activity
  申请人：——

  公开号：US20040102464A1

  公开（公告）日：2004-05-27

  The invention relates to novel aryl-alkane-sulfonamides and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.

  这项发明涉及新型芳基-烷基-磺酰胺及其在制备药物组合物中作为活性成分的用途。该发明还涉及相关方面，包括制备这些化合物的过程、含有其中一种或多种化合物的药物组合物，特别是它们作为内皮素受体拮抗剂的用途。
• Novel arylethene-sulfonamides
  申请人：——

  公开号：US20030220359A1

  公开（公告）日：2003-11-27

  The invention relates to novel aryl-ethene-sulfonamides and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.

  这项发明涉及新颖的芳基乙烯磺酰胺及其在制备药物组合物中作为活性成分的用途。该发明还涉及相关方面，包括制备这些化合物的过程、含有其中一个或多个化合物的药物组合物，特别是它们作为内皮素受体拮抗剂的用途。
• Arylethene-sulfonamides
  申请人：Boss Christoph

  公开号：US06951856B2

  公开（公告）日：2005-10-04

  The invention relates to novel aryl-ethene-sulfonamides and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.

  本发明涉及新型芳基乙烯磺酰胺及其在制备药物组合物中作为活性成分的应用。本发明还涉及相关方面，包括制备该化合物的过程、含有其中一种或多种该化合物的药物组合物，尤其是它们作为内皮素受体拮抗剂的应用。
• ARYLETHENE-SULFONAMIDES, THEIR PREPARATION AND THEIR USE AS ENDOTHELIN ANTAGONISTS
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP1309564A2

  公开（公告）日：2003-05-14
• ARYLALKANE-SULFONAMIDES HAVING ENDOTHELIN-ANTAGONIST ACTIVITY
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP1322624B1

  公开（公告）日：2009-10-21