5-溴-3-[2-(1-吡咯烷基)乙基]-1H-吲哚 | 17274-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-溴-3-[2-(1-吡咯烷基)乙基]-1H-吲哚
• 中文别名: 5-溴-3-[2-(1-吡咯烷)乙基]-1H-吲哚
• 英文名称: 5-bromo-3-(2-pyrrolidinylethyl)-1H-indole
• 英文别名: 5-bromo-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole；5-bromo-3-(2-pyrrolidin-1-ylethyl)-1H-indole
• CAS: 17274-68-9
• 化学式: C₁₄H₁₇BrN₂
• 分子量: 293.206
• InChiKey: OTKDIZOYQXFTDK-UHFFFAOYSA-N

物化性质

• 沸点：
  419.5±30.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-溴-3-[2-(1-吡咯烷基)乙基]-1H-吲哚 在 叔丁基锂 、 sodium hexamethyldisilazane 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 24.0h， 生成 3-(2-Pyrrolidin-1-yl-ethyl)-5-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole
  参考文献：
  名称：

  3-(2-Pyrrolidin-1-ylethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole derivatives as high affinity human 5-HT1B/1D ligands

  摘要：

  A series of 3-(2-pyrrolidin-1-ylethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole derivatives (2) has been prepared using parallel synthesis techniques, and their structure-activity relationships studied. High affinity human 5-HT1B/1D (h5-HT1B/1D) ligands have been identified. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.023
• 作为产物：
  描述：

  2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-溴-3-[2-(1-吡咯烷基)乙基]-1H-吲哚
  参考文献：
  名称：

  5-CYCLO INDOLE COMPOUNDS AS 5-HT1D RECEPTOR LIGANDS

  摘要：

  公开号：

  EP0944595B1

文献信息

• [EN] INDOLE COMPOUNDS AND METHODS FOR TREATING VISCERAL PAIN<br/>[FR] COMPOSÉS D'INDOLE ET PROCÉDÉS DE TRAITEMENT DE LA DOULEUR VISCÉRALE
  申请人：NEURAXON INC

  公开号：WO2009062319A1

  公开（公告）日：2009-05-22

  The invention features methods of treating visceral pain or a condition in a mammal caused by the action of nitric oxide synthase (NOS) or by the action of serotonin 5HT1D/1B receptors, by administering to a patient in need thereof a therapeutically effective amount of an indole compound of Formula (I), or a pharmaceutically acceptable salt or prodrug thereof. The methods of the invention may further comprise the administration of additional therapeutic agent. The invention also features new compounds of Formula (I), pharmaceutical compositions thereof, and methods of resolving enantiomeric mixtures.

  该发明涉及治疗哺乳动物体内因一氧化氮合酶（NOS）或5-羟色胺受体5HT1D/1B的作用引起的内脏疼痛或疾病的方法，通过向需要治疗的患者施用式(I)的吲哚化合物的治疗有效量，或其药学上可接受的盐或前药。该发明的方法还可以包括额外治疗剂的施用。该发明还涉及式(I)的新化合物、其药物组合物以及解决对映体混合物的方法。
• 5-cyclo indole compounds
  申请人：Allelix Biopharmaceuticals, Inc.

  公开号：US05998438A1

  公开（公告）日：1999-12-07

  Described herein are compounds selective for a 5-HT.sub.1D -like receptor, which have the general formula: ##STR1## wherein A is selected from a six-membered, non-aromatic, optionally substituted carbocycle and a six-membered, non-aromatic, optionally substituted heterocycle having one or two heteroatoms selected from O, S, SO, SO.sub.2 and N.sup.4 ; R.sup.1 is selected from H and OH; n is 0 or 1 as permited by chemical structure; R.sup.2 is selected from CR.sup.5 CR.sup.6 CH.sub.2 NR.sup.7 R.sup.8 or a group of formula II, III or IV: ##STR2## R.sup.3 is selected from H and benzoyl; R.sup.4 is selected from H, loweralkyl, benzyl, loweralkylcarbonyl, loweralkylaminocarbonyl, loweralkylaminothiocarbonyl, loweralkanoyl, loweralkylaminoimide and loweralkoxy-substituted loweralkylene; R.sup.5 and R.sup.6 are independently selected from H, loweralkoxy and hydroxy; R.sup.7 and R.sup.8 are independently selected from H and loweralkyl or R.sup.7 and R.sup.8 form an alkylene bridge which, together with the nitrogen atom to which they are attached, creates an optionally substituted 3- to 6-membered ring; denotes a single or double bond; and R.sup.9, R.sup.10 and R.sup.11 are independently selected from H and loweralkyl. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of a 5-HT.sub.1D -like receptor is implicated, such as migraine.

  本文描述了选择性作用于5-HT.sub.1D类受体的化合物，其具有以下通式：##STR1## 其中A选自具有一个或两个O、S、SO、SO.sub.2和N.sup.4杂原子的六元非芳香族、可选取取代基的碳环和六元非芳香族、可选取取代基的杂环；R.sup.1选自H和OH；n根据化学结构可以为0或1；R.sup.2选自CR.sup.5CR.sup.6CH.sub.2NR.sup.7R.sup.8或式II、III或IV的基团：##STR2## R.sup.3选自H和苯甲酰基；R.sup.4选自H、低碳基、苯甲基、低碳基羰基、低碳基氨基羰基、低碳基氨基硫代羰基、低碳酰基、低碳基氨基亚胺和低碳氧基取代的低碳基亚烷基；R.sup.5和R.sup.6独立选自H、低碳氧基和羟基；R.sup.7和R.sup.8独立选自H和低碳基，或者R.sup.7和R.sup.8形成一个烷基桥，该桥与它们所连接的氮原子一起形成一个可选取取代基的3-6元环；表示单键或双键；R.sup.9、R.sup.10和R.sup.11独立选自H和低碳基。还描述了将这些化合物用作药物治疗5-HT.sub.1D类受体受刺激的病症，如偏头痛。
• 5-alkenyl and 5-alkynyl indole compounds
  申请人：Allelix Biopharmaceuticals Inc.

  公开号：US05856510A1

  公开（公告）日：1999-01-05

  Described herein are compounds selective for 5-HT.sub.1D -like receptors, which have the general formula: ##STR1## wherein: R.sup.1 is selected from H, aryl and aryl substituted with 1, 2 or 3 substituents independently selected from loweralkyl, loweralkoxy, loweralkylcarbonyl, loweralkyl-S--, loweralkyl-S(O)--, loweralkyl-SO.sub.2 -, S.dbd.C.dbd.N--, O.dbd.C.dbd.N--, halo, loweralkoxycarbonyl, nitro, amino, loweralkyl-NH--, (loweralkyl).sub.2 --N--, loweralkyl-SO.sub.2 -loweralkyl-; A is a double or triple bond; R.sup.2 is selected from a group of Formula II, III, IV and V: ##STR2## R.sup.3 is selected from H and loweralkyl; R.sup.4 is selected from H and loweralkyl; One of R.sup.5 and R.sup.6 is H and the other is independently selected from H, loweralkoxy, loweralkyl and hydroxy; and R.sup.7 and R.sup.8 are independently selected from H and loweralkyl or R.sup.7 and R.sup.8, together with the nitrogen atom to which they are attached, form an optionally substituted 3- to 6-membered ring; or a salt, solvate or hydrate thereof. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of the 5-HT.sub.1D -like receptor is implicated, such as migraine.

  本文描述了选择性作用于5-HT.sub.1D-类似受体的化合物，其具有以下通式：##STR1## 其中：R.sup.1选自H，芳基和芳基取代物，所述芳基取代物独立地选自较低的烷基，较低的烷氧基，较低的烷基羰基，较低的烷基-S--，较低的烷基-S（O）--，较低的烷基-SO.sub.2-，S.dbd.C.dbd.N--，O.dbd.C.dbd.N--，卤素，较低的烷氧羰基，硝基，氨基，较低的烷基-NH--，（较低的烷基）.sub.2--N--，较低的烷基-SO.sub.2-较低的烷基-; A是双键或三键; R.sup.2选自以下公式II，III，IV和V的一组：##STR2## R.sup.3选自H和较低的烷基; R.sup.4选自H和较低的烷基; R.sup.5和R.sup.6中的一个是H，另一个是独立选自H，较低的烷氧基，较低的烷基和羟基的基团; R.sup.7和R.sup.8独立地选自H和较低的烷基，或者R.sup.7和R.sup.8与它们附着的氮原子一起形成一个可选取代的3-至6-成员环；或其盐，溶剂化合物或水合物。还描述了将这些化合物用作制药用于治疗刺激5-HT.sub.1D-类似受体的症状，例如偏头痛。
• 5-Bicycloindole compounds
  申请人：NPS Allelix Corp.

  公开号：US06329390B1

  公开（公告）日：2001-12-11

  Disclosed herein are compounds selective for a 5-HT1D receptor, the compounds having the general formula (I): Also disclosed is the use of these compounds as pharmaceuticals to treat indications where stimulation of a 5-HT1D receptor is indicated such as migrane.

  本文揭示了具有选择性5-HT1D受体的化合物，这些化合物具有通式（I）：同时，本文还揭示了将这些化合物用作药物治疗刺激5-HT1D受体的适应症，如偏头痛。
• Indole compounds and methods for treating visceral pain
  申请人：Maddaford Shawn

  公开号：US08673909B2

  公开（公告）日：2014-03-18

  The invention features methods of treating visceral pain or a condition in a mammal caused by the action of nitric oxide synthase (NOS) or by the action of serotonin 5HT1D/1B receptors, by administering to a patient in need thereof a therapeutically effective amount of an indole compound of Formula (I), or a pharmaceutically acceptable salt or prodrug thereof. The methods of the invention may further comprise the administration of additional therapeutic agent. The invention also features new compounds of Formula (I), pharmaceutical compositions thereof, and methods of resolving enantiomeric mixtures.

  该发明涉及治疗哺乳动物体内由一氧化氮合酶（NOS）或5-羟色胺5HT1D / 1B受体作用引起的内脏疼痛或疾病的方法，通过向需要治疗的患者施用式（I）的吲哚化合物或其药学上可接受的盐或前药的治疗有效量。该发明的方法还可以进一步包括给予额外的治疗剂量。该发明还涉及式（I）的新化合物、其药物组成物以及解决对映体混合物的方法。