5-氟-7-甲氧基苯并呋喃 | 246029-00-5

• 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-7-甲氧基苯并呋喃
• 英文名称: 5-fluoro-7-methoxybenzofuran
• 英文别名: 5-Fluoro-7-methoxy-1-benzofuran
• CAS: 246029-00-5
• 化学式: C₉H₇FO₂
• 分子量: 166.152
• InChiKey: MKVHAFSUZXHLMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氟-7-甲氧基苯并呋喃 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到5-氟-7-羟基苯并呋喃
  参考文献：
  名称：

  Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of N-Aryloxyethylindolylalkylamines

  摘要：

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.

  DOI：

  10.1021/jm0304010
• 作为产物：
  描述：

  4-氟-2-甲氧基苯酚 在 PPA 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 0.5h， 生成 5-氟-7-甲氧基苯并呋喃
  参考文献：
  名称：

  Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of N-Aryloxyethylindolylalkylamines

  摘要：

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.

  DOI：

  10.1021/jm0304010

文献信息

• N-ARYLOXYETHYLAMINE DERIVATIVES FOR THE TREATMENT OF DEPRESSION
  申请人：Wyeth

  公开号：EP1068184B1

  公开（公告）日：2002-09-04
• US6110956A
  申请人：——

  公开号：US6110956A

  公开（公告）日：2000-08-29
• [EN] N-ARYLOXYETHYLAMINE DERIVATIVES FOR THE TREATMENT OF DEPRESSION<br/>[FR] N-ARYLOXYETHYLAMINES UTILISEES POUR LE TRAITEMENT DE LA DEPRESSION
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：WO1999051576A1

  公开（公告）日：1999-10-14

  (EN) Compounds effective in treating disorders of the serotonin-affected neurological systems are provided, such compounds having (I), wherein: R1 and R2 are each, independently, hydrogen, halogen, CF3, lower alkyl, lower alkoxy, MeSO2, or together can form a 5-7 membered carbocyclic or heterocyclic ring; R3 is alkoxy, halogen, hydrogen or carbamoyl; R4 is hydrogen, hydroxy, lower alkyl, or lower alkoxy; R5 is hydrogen, lower alkyl, or halogen; R6 is hydrogen, lower alkyl, or phenyl; R7 is hydrogen, loyer alkyl, lower alkoxy, halogen, CN, CF3, or hydroxy; and X is (CH2)n, wherein n is 0 to 3; or pharmaceutically acceptable salts thereof.(FR) L'invention concerne des composés efficaces pour le traitement des troubles des systèmes neurologiques influencés par la sérotonine. Ces composés sont représentés par la formule (I), dans laquelle R1 et R2 représentent chacun indépendamment hydrogène, halogène, CF3, alkyle inférieur, alcoxy inférieur, MeSO2 ou peuvent former ensemble un noyau carbocyclique ou hétérocyclique à 5-7 éléments; R3 représente alcoxy, halogène, hydrogène ou carbamyle; R4 représente hydrogène, hydroxy, alkyle inférieur ou alcoxy inférieur; R5 représente hydrogène alkyle inférieur ou halogène; R6 représente hydrogène, alkyle inférieur ou phényle; R7 représente hydrogène, alkyle inférieur, alcoxy inférieur, halogène, CN, CF3 ou hydroxy; et X représente (CH2)n, où n est compris entre 0 et 3. L'invention concerne également des sels pharmaceutiquement acceptables desdits composés.
• Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of <i>N</i>-Aryloxyethylindolylalkylamines
  作者：Richard E. Mewshaw、Dahui Zhou、Ping Zhou、Xiaojie Shi、Geoffrey Hornby、Taylor Spangler、Rosemary Scerni、Deborah Smith、Lee E. Schechter、Terrance H. Andree

  DOI：10.1021/jm0304010

  日期：2004.7.1

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.