(2-氯吡啶-3-基)-(3-氟苯基)甲酮 | 654059-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2-氯吡啶-3-基)-(3-氟苯基)甲酮
• 英文名称: 2-chloro-(3-pyridyl) 3-fluorophenyl ketone
• 英文别名: Methanone, (2-chloro-3-pyridinyl)(3-fluorophenyl)-；(2-chloropyridin-3-yl)-(3-fluorophenyl)methanone
• CAS: 654059-02-6
• 化学式: C₁₂H₇ClFNO
• 分子量: 235.645
• InChiKey: FYQFJTFVSFCZTO-UHFFFAOYSA-N

物化性质

• 沸点：
  367.6±32.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-氯吡啶-3-基)-(3-氟苯基)甲酮 在 potassium hydrogensulfate 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 3-fluorophenyl 2-[(4-methylsulfonyl)phenyl](3-pyridyl) ketone
  参考文献：
  名称：

  3-[4-(Methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) Phenyl Ketone as a Potent and Orally Active Cyclooxygenase-2 Selective Inhibitor:  Synthesis and Biological Evaluation

  摘要：

  Incorporation of a spacer group between the central scaffold and the aryl ring resulted in a new cyclooxygenase-2 (COX-2) selective inhibitor core structure, 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone (20), with COX-2 IC50 = 0.25 mu M and COX-1 IC50 = 14 mu M (human whole blood assay). Compound 20 was orally active in the rat air pouch model of inflammation, inhibiting white blood cell infiltration and COX-2-derived PG production. Our data support the identification of a novel COX-2 selective inhibitor core structure exemplified by 20.

  DOI：

  10.1021/jm0582064
• 作为产物：
  描述：

  2-氯烟酰氯 、 间溴氟苯 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以2.35 g的产率得到(2-氯吡啶-3-基)-(3-氟苯基)甲酮
  参考文献：
  名称：

  3-[4-(Methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) Phenyl Ketone as a Potent and Orally Active Cyclooxygenase-2 Selective Inhibitor:  Synthesis and Biological Evaluation

  摘要：

  Incorporation of a spacer group between the central scaffold and the aryl ring resulted in a new cyclooxygenase-2 (COX-2) selective inhibitor core structure, 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone (20), with COX-2 IC50 = 0.25 mu M and COX-1 IC50 = 14 mu M (human whole blood assay). Compound 20 was orally active in the rat air pouch model of inflammation, inhibiting white blood cell infiltration and COX-2-derived PG production. Our data support the identification of a novel COX-2 selective inhibitor core structure exemplified by 20.

  DOI：

  10.1021/jm0582064

文献信息

• Cyclooxygenase-2 selective inhibitors, compositions and methods of use
  申请人：NitroMed, Inc.

  公开号：US20040072883A1

  公开（公告）日：2004-04-15

  The invention describes novel cyclooxygenase 2 (COX-2) selective inhibitors and novel compositions comprising at least one cyclooxygenase 2 (COX-2) selective inhibitor, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one COX-2 selective inhibitor, optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor, and/or, optionally, at least one therapeutic agent. The novel cyclooxygenase 2 selective inhibitors of the invention can be optionally nitrosated and/or nitrosylated. The invention also provides methods for treating inflammation, pain and fever; for treating and/or improving the gastrointestinal properties of COX-2 selective inhibitors; for facilitating wound healing; for treating and/or preventing renal and/or respiratory toxicity; for treating and/or preventing other disorders resulting from elevated levels of cyclooxygenase-2; and for improving the cardiovascular profile of COX-2 selective inhibitors.

  本发明描述了新型环氧合酶2（COX-2）选择性抑制剂和包含至少一种环氧合酶2（COX-2）选择性抑制剂的新型组合物，以及可选地，至少一种捐赠、转移或释放一氧化氮、刺激内源性一氧化氮合成、提高内源性内皮衍生松弛因子水平或是一氧化氮合酶底物的化合物，和/或至少一种治疗剂。本发明还提供了包含至少一种COX-2选择性抑制剂、可选地亚硝化和/或亚硝酰化，以及可选地至少一种一氧化氮给体和/或至少一种治疗剂的新型试剂盒。本发明的新型环氧合酶2选择性抑制剂可选择性地亚硝化和/或亚硝酰化。本发明还提供了治疗炎症、疼痛和发热的方法；用于治疗和/或改善COX-2选择性抑制剂的胃肠道特性；促进伤口愈合的方法；用于治疗和/或预防肾脏和/或呼吸毒性的方法；用于治疗和/或预防由于环氧合酶-2水平升高而引起的其他疾病的方法；以及用于改善COX-2选择性抑制剂的心血管特性的方法。
• SUBSTITUTED 1,2,4-OXADIAZOLES AND ANALOGS THEREOF AS CB2 RECEPTOR MODULATORS, USEFUL IN THE TREATMENT OF PAIN, RESPIRATORY AND NON-RESPIRATORY DISEASES
  申请人：Wu Zhicai

  公开号：US20100227845A1

  公开（公告）日：2010-09-09

  The present invention relates to compounds represented by Formula (I), Formula (II) and Formula (III) and pharmaceutically acceptable salts thereof. The present invention also provides pharmaceutical compositions comprising the instant compounds. This invention further provides methods to treat and prevent pain, respiratory and non-respiratory diseases.

  本发明涉及由公式（I）、公式（II）和公式（III）所代表的化合物及其药学上可接受的盐。本发明还提供包含这些化合物的制药组合物。本发明还提供治疗和预防疼痛、呼吸和非呼吸疾病的方法。
• CYCLOOXYGENASE- 2 SELECTIVE INHIBITORS, COMPOSITIONS AND METHODS OF USE
  申请人：Nitromed, Inc.

  公开号：EP1542972A2

  公开（公告）日：2005-06-22
• EP1542972A4
  申请人：——

  公开号：EP1542972A4

  公开（公告）日：2008-01-23
• US7244753B2
  申请人：——

  公开号：US7244753B2

  公开（公告）日：2007-07-17