(5-fluoro-1H-indol-2-yl)-(4-(pyridin-2-yl)-piperazin-1-yl)methanone | 220941-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (5-fluoro-1H-indol-2-yl)-(4-(pyridin-2-yl)-piperazin-1-yl)methanone
• 英文别名: (5-Fluoro-1H-indol-2-yl)-(4-pyridin-2-yl-piperazin-1-yl)-methanone；5-fluoro-2-{[4-(2-pyridinyl)-1-Piperazinyl]carbonyl}-1H-indole；(5-fluoro-1H-indol-2-yl)-(4-pyridin-2-ylpiperazin-1-yl)methanone
• CAS: 220941-96-8
• 化学式: C₁₈H₁₇FN₄O
• 分子量: 324.358
• InChiKey: GIPXMXAYTYHIKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-fluoro-1H-indol-2-yl)-(4-(pyridin-2-yl)-piperazin-1-yl)methanone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 5-氟-2-{[4-(2-吡啶)-1-哌嗪]甲基}-1H-吲哚
  参考文献：
  名称：

  [EN] FUSED BICYCLIC AROMATIC COMPOUNDS THAT ARE USEFUL IN TREATING SEXUAL DYSFUNCTION
  [FR] COMPOSES AROMATIQUES BICYCLIQUES CONDENSES UTILES DANS LE TRAITEMENT DE DYSFONCTIONNEMENT SEXUEL

  摘要：

  本发明涉及使用化合物(I)的治疗性功能障碍，并涉及含有化合物(I)的组合物用于治疗性功能障碍。

  公开号：

  WO2003101994A1
• 作为产物：
  描述：

  1-(2-吡啶基)哌嗪 、 5-氟吲哚-2-甲酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以64%的产率得到(5-fluoro-1H-indol-2-yl)-(4-(pyridin-2-yl)-piperazin-1-yl)methanone
  参考文献：
  名称：

  [EN] FUSED BICYCLIC AROMATIC COMPOUNDS THAT ARE USEFUL IN TREATING SEXUAL DYSFUNCTION
  [FR] COMPOSES AROMATIQUES BICYCLIQUES CONDENSES UTILES DANS LE TRAITEMENT DE DYSFONCTIONNEMENT SEXUEL

  摘要：

  本发明涉及使用化合物(I)的治疗性功能障碍，并涉及含有化合物(I)的组合物用于治疗性功能障碍。

  公开号：

  WO2003101994A1

文献信息

• Fused bicyclic aromatic compounds that are useful in treating sexual dysfunction
  申请人：Cowart D. Marlon

  公开号：US20060172995A1

  公开（公告）日：2006-08-03

  The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction, wherein A, L, D and B, are as described in the specification.

  本发明涉及使用公式(I)化合物的用途，用于治疗性功能障碍，以及包含用于治疗性功能障碍的公式(I)化合物的组合物，其中A、L、D和B如说明书中所述。
• 2-(4-aryl or heteroaryl-piperazin-1-ylmethyl)-1H-indole derivatives interacting with the dopamine D4 receptor
  申请人：Pfizer Inc.

  公开号：US20030100757A1

  公开（公告）日：2003-05-29

  A compound of the formula 1 wherein a, T, V, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are as defined above, their pharmaceutically acceptable salts and pharmaceutical compositions containing such compounds or their salts.

  该化合物的公式为1，其中a、T、V、X、Y、Z、R1、R2、R3、R4、R5、R6、R7、R8和R9如上所定义，其药学上可接受的盐和含有这种化合物或其盐的制药组合物。
• 2-(4-Aryl or heteroaryl-piperazin-1-ylmethyl)-1H-indole derivatives interacting with the dopamine
  申请人：Pfizer Inc

  公开号：US20040198734A1

  公开（公告）日：2004-10-07

  A compound of the formula 1 wherein a, T, V, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are as defined above, their pharmaceutically acceptable salts and pharmaceutical compositions containing such compounds or their salts.

  该化合物的化学式为1，其中a，T，V，X，Y，Z，R1，R2，R3，R4，R5，R6，R7，R8和R9的定义如上所述，其药学上可接受的盐和含有这种化合物或其盐的制药组合物。
• Fused Bicyclic Aromatic Compounds that are Useful in Treating Sexual Dysfunction
  申请人：Cowart D. Marlon

  公开号：US20070265249A1

  公开（公告）日：2007-11-15

  The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction, wherein A, L, D and B 1 are as described in the specification.

  本发明涉及使用式（I）化合物治疗性功能障碍以及含有式（I）化合物的组合物治疗性功能障碍，其中A、L、D和B1如说明书所述。
• Discovery of 2-(4-Pyridin-2-ylpiperazin-1-ylmethyl)-1<i>H</i>-benzimidazole (ABT-724), a Dopaminergic Agent with a Novel Mode of Action for the Potential Treatment of Erectile Dysfunction
  作者：Marlon Cowart、Steven P. Latshaw、Pramila Bhatia、Jerome F. Daanen、Jeffrey Rohde、Sherry L. Nelson、Meena Patel、Teodozyi Kolasa、Masaki Nakane、Marie E. Uchic、Loan N. Miller、Marc A. Terranova、Renjie Chang、Diana L. Donnelly-Roberts、Marian T. Namovic、Peter R. Hollingsworth、Brenda R. Martino、James J. Lynch、James P. Sullivan、Gin C. Hsieh、Robert B. Moreland、Jorge D. Brioni、Andrew O. Stewart

  DOI：10.1021/jm030505a

  日期：2004.7.1

  A new class of agents with potential utility for the treatment of erectile dysfunction has been discovered, guided by the hypothesis that selective D-4 agonists are erectogenic but devoid of the side effects typically associated with dopaminergic agents. The lead agent 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (1, ABT-724) was discovered by optimization of a series of benzimidazole arylpiperazines. This highly selective D-4 agonist was found to be very potent and efficacious in vivo, eliciting penile erections in rats at a dose of 0.03 mumol/kg, with a positive response rate of 77% erectile incidence. Even at high doses, it was devoid of side effects in animal models of central nervous system behaviors, emesis, or nausea. The structure-activity relationship of the parent benzimidazole series leading to 1 is described, with the detailed in vitro and in vivo profiles described. Distinctive structural features were discovered that are associated with D-4 selective agonism in this series of analogues.