5-氟苯并呋喃-3-甲醛 | 721943-19-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 5-氟苯并呋喃-3-甲醛
• 中文别名: 5-氟-3-醛基苯并呋喃
• 英文名称: 5-fluorobenzofuran-3-carbaldehyde
• 英文别名: 5-fluoro-1-benzofuran-3-carbaldehyde
• CAS: 721943-19-7
• 化学式: C₉H₅FO₂
• 分子量: 164.136
• InChiKey: LUAQHOIIXDJUOY-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119℃
• 沸点：
  255.7±20.0 °C(Predicted)
• 密度：
  1.342

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氟苯并呋喃-3-甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到5-fluorobenzofuran-3-ylmethanol
  参考文献：
  名称：

  Structure−Activity Relationships for a Novel Series of Dopamine D2-like Receptor Ligands Based on N-Substituted 3-Aryl-8-azabicyclo[3.2.1]octan-3-ol

  摘要：

  Discovering dopamine D2-like receptor subtype-selective ligands has been a focus of significant investigation. The D2R-selective antagonist 3-[4-(4-chlorophenyl)-4-hydroxypiperidinyl]methylindole (1, L741,626; K-i(D2R/MR) = 11.2:163 nM) has previously provided a lead template for chemical modification. Herein, analogues have been synthesized where the piperidine was replaced by a tropane ring that reversed the selectivity seen in the parent compound, in human hD2(L)R- or hD3R-transfected HEK 293 cells (31, K-i(D2R/D3R) = 33.4: 15.5 nM). Further exploration of both N-substituted and aryl ring-substituted analogues resulted in the discovery of several high affinity D2R/D3R ligands with 3-benzofurylmethyl-substituents (e.g., 45, K-i(D2R/D3R) = 1.7:0.34 nM) that induced high affinity not achieved in similarly N-substituted piperidine analogues and significantly (470-fold) improved D3R binding affinity compared to the parent ligand 1. X-ray crystallographic data revealed a distinctive spatial arrangement of pharmacophoric elements in the piperidinol vs tropine analogues, providing clues for the diversity in SAR at the D2 and D3 receptor subtypes.

  DOI：

  10.1021/jm800532x
• 作为产物：
  描述：

  5-氟-3-甲基苯并呋喃 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以28%的产率得到5-氟苯并呋喃-3-甲醛
  参考文献：
  名称：

  Structure−Activity Relationships for a Novel Series of Dopamine D2-like Receptor Ligands Based on N-Substituted 3-Aryl-8-azabicyclo[3.2.1]octan-3-ol

  摘要：

  Discovering dopamine D2-like receptor subtype-selective ligands has been a focus of significant investigation. The D2R-selective antagonist 3-[4-(4-chlorophenyl)-4-hydroxypiperidinyl]methylindole (1, L741,626; K-i(D2R/MR) = 11.2:163 nM) has previously provided a lead template for chemical modification. Herein, analogues have been synthesized where the piperidine was replaced by a tropane ring that reversed the selectivity seen in the parent compound, in human hD2(L)R- or hD3R-transfected HEK 293 cells (31, K-i(D2R/D3R) = 33.4: 15.5 nM). Further exploration of both N-substituted and aryl ring-substituted analogues resulted in the discovery of several high affinity D2R/D3R ligands with 3-benzofurylmethyl-substituents (e.g., 45, K-i(D2R/D3R) = 1.7:0.34 nM) that induced high affinity not achieved in similarly N-substituted piperidine analogues and significantly (470-fold) improved D3R binding affinity compared to the parent ligand 1. X-ray crystallographic data revealed a distinctive spatial arrangement of pharmacophoric elements in the piperidinol vs tropine analogues, providing clues for the diversity in SAR at the D2 and D3 receptor subtypes.

  DOI：

  10.1021/jm800532x

文献信息

• [EN] 1,2,4-TRIAMINOBENZENE DERIVATIVES USEFUL FOR TREATING DISORDERS OF THE CENTRAL NERVOUS SYSTEM<br/>[FR] DÉRIVÉS DE 1,2,4-TRIAMINOBENZÈNE UTILES POUR TRAITER DES TROUBLES DU SYSTÈME NERVEUX CENTRAL
  申请人：LUNDBECK & CO AS H

  公开号：WO2004058739A1

  公开（公告）日：2004-07-15

  The present invention concerns 1,2,4-triaminobenzene derivatives of the general formula I or pharmaceutically acceptable salts thereof and the use thereof.

  这项发明涉及通式I的1,2,4-三氨基苯衍生物或其药用可接受的盐以及它们的用途。
• 1,2,4-Triaminobenzene derivatives useful for treating disorders of the central nervous system
  申请人：Rottlander Mario

  公开号：US20060014822A1

  公开（公告）日：2006-01-19

  The present invention concerns 1,2,4-triaminobenzene derivatives of the general formula I or pharmaceutically acceptable salts thereof and the use thereof.

  本发明涉及通式I的1,2,4-三氨基苯衍生物或其药学上可接受的盐以及其用途。
• 1,2,4-TRIAMINOBENZENE DERIVATIVES USEFUL FOR TREATING DISORDERS OF THE CENTRAL NERVOUS SYSTEM
  申请人：H. LUNDBECK A/S

  公开号：EP1578740B1

  公开（公告）日：2007-03-21
• US7368472B2
  申请人：——

  公开号：US7368472B2

  公开（公告）日：2008-05-06
• Structure−Activity Relationships for a Novel Series of Dopamine D2-like Receptor Ligands Based on N-Substituted 3-Aryl-8-azabicyclo[3.2.1]octan-3-ol
  作者：Noel M. Paul、Michelle Taylor、Rakesh Kumar、Jeffrey R. Deschamps、Robert R. Luedtke、Amy Hauck Newman

  DOI：10.1021/jm800532x

  日期：2008.10.9

  Discovering dopamine D2-like receptor subtype-selective ligands has been a focus of significant investigation. The D2R-selective antagonist 3-[4-(4-chlorophenyl)-4-hydroxypiperidinyl]methylindole (1, L741,626; K-i(D2R/MR) = 11.2:163 nM) has previously provided a lead template for chemical modification. Herein, analogues have been synthesized where the piperidine was replaced by a tropane ring that reversed the selectivity seen in the parent compound, in human hD2(L)R- or hD3R-transfected HEK 293 cells (31, K-i(D2R/D3R) = 33.4: 15.5 nM). Further exploration of both N-substituted and aryl ring-substituted analogues resulted in the discovery of several high affinity D2R/D3R ligands with 3-benzofurylmethyl-substituents (e.g., 45, K-i(D2R/D3R) = 1.7:0.34 nM) that induced high affinity not achieved in similarly N-substituted piperidine analogues and significantly (470-fold) improved D3R binding affinity compared to the parent ligand 1. X-ray crystallographic data revealed a distinctive spatial arrangement of pharmacophoric elements in the piperidinol vs tropine analogues, providing clues for the diversity in SAR at the D2 and D3 receptor subtypes.