(2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol | 1031849-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol
• 英文别名: (4-phenyl-10-oxa-5,6-diazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7-tetraen-3-yl)methanol
• CAS: 1031849-25-8
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: WPEKECBLKBFIIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol 在 三氟化硼乙醚 、 氨 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanamine
  参考文献：
  名称：

  Synthesis of a Novel Series of Tricyclic Dihydrofuran Derivatives: Discovery of 8,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridines as Melatonin Receptor (MT₁/MT₂) Ligands

  摘要：

  Novel tricyclic dihydrofuran derivatives were designed, synthesized, and evaluated as melatonin receptor (MT1/MT2) ligands based on the previously reported 1,6-dihydro-2H-indeno[5,4-b]furan la. By screening the central tricyclic cores, we identified 8,9-dihydrofuro [3,2-c]pyrazolo [1,5-a]pyridine as a potent scaffold with a high ligand-lipophilicity efficiency (LLE) value. Subsequent optimization of the side chains led to identification of the potent MT1/MT2 agonist 4d (MT1, K-i = 0.062 nM; MT2, K-i = 0.420 nM) with good oral absorption and blood-brain barrier (BBB) penetration in rats. The oral administration of compound 4d exhibited a sleep-promoting action in freely moving cats at 0.1 mg/kg.

  DOI：

  10.1021/jm200385u
• 作为产物：
  描述：

  methyl 2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]-pyridine-1-carboxylate 在 lithium aluminium tetrahydride 、 Glauber's salt 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以90%的产率得到(2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol
  参考文献：
  名称：

  TRICYCLIC COMPOUND AND MEDICAL USE THEREOF

  摘要：

  公开号：

  EP2100895B1

文献信息

• Tricyclic compound and medical use thereof
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US08273761B2

  公开（公告）日：2012-09-25

  The present invention provides a compound represented by the formula wherein R1 is a hydrocarbon group optionally having substituent(s), amino optionally having substituent(s), hydroxy optionally having a substituent or a heterocyclic group optionally having substituent(s), R2 is a hydrogen atom or a hydrocarbon group optionally having substituent(s), R3 is a hydrogen atom, a halogen atom, a hydrocarbon group optionally having substituent(s), amino optionally having substituent(s), hydroxy optionally having a substituent or mercapto optionally having a substituent, Xa to Xe are each a carbon atom or a nitrogen atom, m is 0 to 2, and ring A to ring C are each a ring optionally having substituent(s), or a salt thereof, which is useful as an agent for the prophylaxis or treatment of a disease relating to an action of melatonin, and the like.

  本发明提供了一种化合物，其表示为式中，R1是一个烃基，可选地具有取代基，氨基，可选地具有取代基的羟基或杂环基，R2是氢原子或烃基，可选地具有取代基，R3是氢原子，卤素原子，可选地具有取代基的烃基，氨基，可选地具有取代基的羟基或可选地具有取代基的硫醇基，Xa到Xe分别是碳原子或氮原子，m为0到2，环A到环C分别是可选地具有取代基的环，或其盐，其用作预防或治疗与褪黑激素作用相关的疾病的药剂等。
• US8273761B2
  申请人：——

  公开号：US8273761B2

  公开（公告）日：2012-09-25