6-[4-(2-Isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl]-pyrimidin-4-ol | 388118-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-[4-(2-Isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl]-pyrimidin-4-ol
• 英文别名: 6-(4-(2-Isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyrimidin-4-ol；4-[4-(2-propan-2-ylphenyl)sulfanyl-3-(trifluoromethyl)phenyl]-1H-pyrimidin-6-one
• CAS: 388118-57-8
• 化学式: C₂₀H₁₇F₃N₂OS
• 分子量: 390.429
• InChiKey: ZKSGNXMHHTXSLV-UHFFFAOYSA-N

物化性质

• 沸点：
  455.6±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-[4-(2-Isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl]-pyrimidin-4-ol 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (3-Imidazol-1-yl-propyl)-(6-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyrimidin-4-yl)-amine
  参考文献：
  名称：

  Amino-substituted heterocycles as isosteres of trans-cinnamides: design and synthesis of heterocyclic biaryl sulfides as potent antagonists of LFA-1/ICAM-1 binding

  摘要：

  2-Amino-4-phenyl pyridine and, to a lesser extent, 4-amino-6-phenyl pyrimidine, were established as isosteres of transcinnamide moiety. Applying this isosterism to previously reported p-arylthio cinnamides resulted in the identification of 4-amino-6-(p-arylthio)phenyl-pyrimidines and 2-amino-4-(p-arylthio)phenyl-pyridines as potent antagonists of LFA-1/ICAM-1 binding. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.008
• 作为产物：
  描述：

  2-异丙基苯硫酚 在 sodium hydride 、 caesium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 6-[4-(2-Isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl]-pyrimidin-4-ol
  参考文献：
  名称：

  Amino-substituted heterocycles as isosteres of trans-cinnamides: design and synthesis of heterocyclic biaryl sulfides as potent antagonists of LFA-1/ICAM-1 binding

  摘要：

  2-Amino-4-phenyl pyridine and, to a lesser extent, 4-amino-6-phenyl pyrimidine, were established as isosteres of transcinnamide moiety. Applying this isosterism to previously reported p-arylthio cinnamides resulted in the identification of 4-amino-6-(p-arylthio)phenyl-pyrimidines and 2-amino-4-(p-arylthio)phenyl-pyridines as potent antagonists of LFA-1/ICAM-1 binding. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.008
• 作为试剂：
  描述：

  3-(4-(2-Isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-3-oxo-propionic acid ethyl ester 、 甲脒盐酸盐 、 甲醇 在 6-[4-(2-Isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl]-pyrimidin-4-ol 、 C8 、 NH4OAc H2O CH3CN 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以gave a white solid 46 (1.40 g, 14%)的产率得到6-[4-(2-Isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl]-pyrimidin-4-ol
  参考文献：
  名称：

  Aryl phenylheterocyclyl sulfide derivatives and their use as cell adhesion-inhibiting anti-inflammatory and immune-suppressive agents

  摘要：

  本发明涉及一种新型杂环基含二芳基硫化物化合物，适用于治疗炎症和免疫性疾病，包括包含这些化合物的制药组合物，以及在哺乳动物中抑制炎症或抑制免疫反应的方法。

  公开号：

  US06787542B2

文献信息

• Aryl phenylheterocyclyl sulfide derivatives and their use as cell adhesion-inhibiting anti-inflammatory and immune-supressive agents
  申请人：Wang T. Gary

  公开号：US20050014746A1

  公开（公告）日：2005-01-20

  The present invention relates to novel heterocyclyl-containing diaryl sulfide compounds that are useful for treating inflammatory and immune diseases, to pharmaceutical compositions comprising these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及一种新型含杂环基的二芳基硫化物化合物，可用于治疗炎症和免疫性疾病，还涉及包含这些化合物的制药组合物以及在哺乳动物中抑制炎症或抑制免疫反应的方法。
• ARYL PHENYLHETEROCYCLYL SULFIDE DERIVATIVES AND THEIR USE AS CELL ADHESION-INHIBITING ANTI-INFLAMMATORY AND IMMUNE-SUPPRESSIVE AGENTS
  申请人：Wang T. Gary

  公开号：US20070066585A1

  公开（公告）日：2007-03-22

  The present invention relates to novel heterocyclyl-containing diaryl sulfide compounds that are useful for treating inflammatory and immune diseases, to pharmaceutical compositions comprising these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及一种新的含杂环基的二芳基硫化物化合物，用于治疗炎症和免疫性疾病，包括包含这些化合物的制药组合物，以及在哺乳动物中抑制炎症或抑制免疫反应的方法。
• US7129247B2
  申请人：——

  公开号：US7129247B2

  公开（公告）日：2006-10-31
• [EN] ARYL PHENYLHETEROCYCLYL SULFIDE DERIVATIVES AND THEIR USE AS CELL ADHESION-INHIBITING ANTI-INFLAMMATORY AND IMMUNE-SUPPRESSIVE AGENTS<br/>[FR] DERIVES D'ARYLE PHENYLHETEROCYCLYLE SULFURES ET LEUR UTILISATION EN TANT QU'AGENTS IMMUNOSUPPRESSEURS ANTI-INFLAMMATOIRES INHIBANT L'ADHERENCE CELLULAIRE
  申请人：ABBOTT LAB

  公开号：WO2002002539A1

  公开（公告）日：2002-01-10

  The present invention relates to novel heterocyclyl-containing diaryl sulfide compounds that are useful for treating inflammatory and immune diseases, to pharmaceutical compositions comprising these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.
• Amino-substituted heterocycles as isosteres of trans-cinnamides: design and synthesis of heterocyclic biaryl sulfides as potent antagonists of LFA-1/ICAM-1 binding
  作者：Gary T. Wang、Sheldon Wang、Robert Gentles、Thomas Sowin、Sandra Leitza、Edward B. Reilly、Thomas W. von Geldern

  DOI：10.1016/j.bmcl.2004.10.008

  日期：2005.1

  2-Amino-4-phenyl pyridine and, to a lesser extent, 4-amino-6-phenyl pyrimidine, were established as isosteres of transcinnamide moiety. Applying this isosterism to previously reported p-arylthio cinnamides resulted in the identification of 4-amino-6-(p-arylthio)phenyl-pyrimidines and 2-amino-4-(p-arylthio)phenyl-pyridines as potent antagonists of LFA-1/ICAM-1 binding. (C) 2004 Elsevier Ltd. All rights reserved.