3-bromo-5-(2,5-difluorophenyl)pyridine | 1276123-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-bromo-5-(2,5-difluorophenyl)pyridine
• 英文别名: 3-bromo-5-(2,5-difluoro-phenyl)-pyridine
• CAS: 1276123-22-8
• 化学式: C₁₁H₆BrF₂N
• 分子量: 270.076
• InChiKey: ISIYTCQJCKWAGY-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  301.7±37.0 °C(Predicted)
• 密度：
  1.565±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 、 3-bromo-5-(2,5-difluorophenyl)pyridine 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以82%的产率得到8-[5-(2,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
  参考文献：
  名称：

  Fine-Tuning the Selectivity of Aldosterone Synthase Inhibitors: Structure−Activity and Structure−Selectivity Insights from Studies of Heteroaryl Substituted 1,2,5,6-Tetrahydropyrrolo[3,2,1-ij]quinolin-4-one Derivatives

  摘要：

  Pyridine substituted 3,4-dihydro-1H-quinolin-2-ones (e.g., 1-3) constitute a class of highly potent and selective inhibitors of aldosterone synthase (CYP11B2), a promising target for the treatment of hyperaldosteronism, congestive heart failure, and myocardial fibrosis. Among these, ethyl-substituted 3 possesses high selectivity against CYP1A2. Rigidification of 3 by incorporation of the ethyl group into a 5- or 6-membered ring affords compounds with a pyrroloquinolinone or pyridoquinolinone molecular scaffold (e.g., 4 and 5). It was found that these molecules are even more potent and selective CYP11B2 inhibitors than their corresponding open-chain analogues. Moreover, pyrroloquinolinone 4 exhibits no inhibition of the six most important hepatic CYP enzymes as well as a bioavailability in the range of the marketed drug fadrozole. The SAR studies disclose that subtle changes in the heterocyclic moiety are responsible for either a strong or a weak inhibition of the highly homologous 11 beta-hydroxylase (CYP11B1). These results are not only important for fine-tuning the selectivity of CYP11B2 inhibitors but also for the development of selective CYP11B1 inhibitors that are of interest for the treatment of Cushing's syndrome and metabolic syndrome.

  DOI：

  10.1021/jm101470k
• 作为产物：
  描述：

  3,5-二溴吡啶 、 2,5-二氟苯硼酸 生成 3-bromo-5-(2,5-difluorophenyl)pyridine
  参考文献：
  名称：

  Polycyclic compounds as lysophosphatidic acid receptor antagonists

  摘要：

  本文描述了一些能够拮抗赖氨酸磷酸受体的化合物。同时还描述了包括上述化合物的药物组成物和药物，以及使用这些拮抗剂的方法，单独或联合其他化合物，用于治疗依赖或介导赖氨酸磷酸的疾病或病症。

  公开号：

  US08664220B2

文献信息

• POLYCYCLIC COMPOUNDS AS LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
  申请人：CLARK Ryan

  公开号：US20110082164A1

  公开（公告）日：2011-04-07

  Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in combination with other compounds, for treating LPA-dependent or LPA-mediated conditions or diseases.

  本文描述了一些作为赖氨酸磷脂酸受体拮抗剂的化合物。还描述了包括本文描述的化合物的药物组合物和药物，以及使用这些拮抗剂的方法，单独或与其他化合物结合，用于治疗依赖或介导赖氨酸磷脂酸的疾病或病症。
• Polycyclic compounds as lysophosphatidic acid receptor antagonists
  申请人：Clark Ryan

  公开号：US08664220B2

  公开（公告）日：2014-03-04

  Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in combination with other compounds, for treating LPA-dependent or LPA-mediated conditions or diseases.

  本文描述了一些能够拮抗赖氨酸磷酸受体的化合物。同时还描述了包括上述化合物的药物组成物和药物，以及使用这些拮抗剂的方法，单独或联合其他化合物，用于治疗依赖或介导赖氨酸磷酸的疾病或病症。
• US20140256744A1
  申请人：——

  公开号：——

  公开（公告）日：——
• US8664220B2
  申请人：——

  公开号：US8664220B2

  公开（公告）日：2014-03-04
• US8778983B2
  申请人：——

  公开号：US8778983B2

  公开（公告）日：2014-07-15