(R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-methyl-1H-indole | 244122-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-methyl-1H-indole
• 英文别名: benzyl (2R)-2-(5-methyl-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate
• CAS: 244122-78-9
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: GDBHHLRTUZFPCG-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-methyl-1H-indole 在 palladium-carbon 氨 作用下， 以 甲醇 、 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 以15%的产率得到(R)-5-Methyl-3-[(pyrrolidin-2-yl)carbonyl]-1H-indole
  参考文献：
  名称：

  5-alkyl indole compounds

  摘要：

  本文描述了对5-HT.sub.1D-样受体具有选择性的化合物，其具有以下通用公式：其中：R.sup.1是线性或支链低碳烷基；R.sup.2选自公式II、III、IV和V的一组：R.sup.3选自H和低碳烷基；R.sup.4选自H和低碳烷基；R.sup.5和R.sup.6中的一个是H，另一个独立选自H、低碳氧基、低碳烷基和羟基；n为1-3；或其盐、溶剂合物或水合物。还描述了将这些化合物用作药物治疗刺激5-HT.sub.1D-样受体相关的适应症，如偏头痛。

  公开号：

  US05998462A1
• 作为产物：
  描述：

  5-甲基吲哚 、 N-benzyloxycarbonyl-D-proline acid chloride 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-methyl-1H-indole
  参考文献：
  名称：

  5-Alkyltryptamine derivatives as highly selective and potent 5-HT1D receptor agonists

  摘要：

  A series of 5-alkyltryptamines (6) and the corresponding conformationally constrained analogues (8) have been synthesized. The structure-activity relationships (SAR) at the 5-position of the indole skeleton and the ethylamine side chain have been studied. Functional activities were assessed using isolated rabbit saphenous vein. Potent, selective ligands were found (6e, K-i 2.5 nM, 5-HT1B/5-HT1D 125-fold) that have potential for treating acute migraine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00322-x

文献信息

• Pyrrolidine-indole compounds having 5-HT.sub.6 affinity
  申请人：Allelix Biopharmaceuticals Inc.

  公开号：US06100291A1

  公开（公告）日：2000-08-08

  Described herein are compounds with affinity for the 5-HT.sub.6 receptor, which have the general formula: ##STR1## wherein: R.sup.1 is selected from the group consisting of H and C.sub.1-4 alkyl; R.sup.2 is selected from the group consisting of H, C.sub.1-4 alkyl and benzyl; R.sup.3 is selected from the group consisting of COR.sup.5, SO.sub.2 R.sup.5, CONHC.sub.1-4 alkyl and C(S)SR.sup.6 ; R.sup.4a is selected from the group consisting of H, OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; R.sup.4b is selected from the group consisting of H, hydroxy, halo, C.sub.3-7 cycloalkyloxy, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, benzyloxy, phenoxy, trifluoromethyl, trifluoromethoxy and vinyl; R.sup.4c is selected from the group consisting of H, OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; R.sup.4d is selected from the group consisting of H, OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; R.sup.5 is selected from the group consisting of phenyl, pyridyl, thienyl, quinolinyl and naphthyl which are optionally substituted with 1-4 substituents selected from C.sub.1-4 alkoxy, C.sub.1-4 alkyl, halo, nitro, trifluoromethyl, trifluoromethoxy, 1,2-methylenedioxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl and C.sub.1-4 alkylS--; and R.sup.6 is selected from C.sub.1-4 alkyl, allyl, propargyl and optionally substituted benzyl wherein the benzyl group is optionally substituted with 1-4 substituents selected from cyano, C.sub.1-4 alkyl and halo. Also described is the use of these compounds as pharmaceuticals to treat indications where inhibition of the 5-HT.sub.6 receptor is implicated, such as schizophrenia.

  本文描述了亲和力与5-HT.sub.6受体相关的化合物，其具有以下一般式：##STR1##其中：R.sup.1选自H和C.sub.1-4烷基组成的群体；R.sup.2选自H、C.sub.1-4烷基和苄基组成的群体；R.sup.3选自COR.sup.5、SO.sub.2R.sup.5、CONHC.sub.1-4烷基和C(S)SR.sup.6组成的群体；R.sup.4a选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基组成的群体；R.sup.4b选自H、羟基、卤素、C.sub.3-7环烷氧基、C.sub.1-4烷氧基、C.sub.1-4烷基、苄氧基、苯氧基、三氟甲基、三氟甲氧基和乙烯基组成的群体；R.sup.4c选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基组成的群体；R.sup.4d选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基组成的群体；R.sup.5选自苯基、吡啶基、噻吩基、喹啉基和萘基，它们可以选择性地用1-4个取代基选自C.sub.1-4烷氧基、C.sub.1-4烷基、卤素、硝基、三氟甲基、三氟甲氧基、1,2-亚甲二氧基、C.sub.1-4烷基羰基、C.sub.1-4烷氧羰基和C.sub.1-4烷基S--;R.sup.6选自C.sub.1-4烷基、烯丙基、丙炔基和可选择性取代的苄基，其中苄基可以选择性地用1-4个取代基选自氰基、C.sub.1-4烷基和卤素。还描述了这些化合物作为药物治疗抑制5-HT.sub.6受体相关症状的用途，如精神分裂症。
• US5998462A
  申请人：——

  公开号：US5998462A

  公开（公告）日：1999-12-07
• US6100291A
  申请人：——

  公开号：US6100291A

  公开（公告）日：2000-08-08
• 5-alkyl indole compounds
  申请人：Allelix Biopharmaceuticals Inc.

  公开号：US05998462A1

  公开（公告）日：1999-12-07

  Described herein are compounds selective for the 5-HT.sub.1D -like receptor, which have the general formula: ##STR1## wherein: R.sup.1 is linear or branched loweralkyl; 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 n is 1-3; 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.

  本文描述了对5-HT.sub.1D-样受体具有选择性的化合物，其具有以下通用公式：其中：R.sup.1是线性或支链低碳烷基；R.sup.2选自公式II、III、IV和V的一组：R.sup.3选自H和低碳烷基；R.sup.4选自H和低碳烷基；R.sup.5和R.sup.6中的一个是H，另一个独立选自H、低碳氧基、低碳烷基和羟基；n为1-3；或其盐、溶剂合物或水合物。还描述了将这些化合物用作药物治疗刺激5-HT.sub.1D-样受体相关的适应症，如偏头痛。
• 5-Alkyltryptamine derivatives as highly selective and potent 5-HT1D receptor agonists
  作者：Abdelmalik Slassi、Louise Edwards、Anne O'Brien、Charles Q Meng、Tao Xin、Caroline Seto、David K.H Lee、Neil MacLean、Donna Hynd、Cora Chen、Hong Wang、Rajender Kamboj、Suman Rakhit

  DOI：10.1016/s0960-894x(00)00322-x

  日期：2000.8

  A series of 5-alkyltryptamines (6) and the corresponding conformationally constrained analogues (8) have been synthesized. The structure-activity relationships (SAR) at the 5-position of the indole skeleton and the ethylamine side chain have been studied. Functional activities were assessed using isolated rabbit saphenous vein. Potent, selective ligands were found (6e, K-i 2.5 nM, 5-HT1B/5-HT1D 125-fold) that have potential for treating acute migraine. (C) 2000 Elsevier Science Ltd. All rights reserved.