1-benzylindoline-6-carboxylic acid | 338959-30-1

• 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
• 英文名称: 1-benzylindoline-6-carboxylic acid
• 英文别名: 1-benzyl-2,3-dihydroindole-6-carboxylic acid
• CAS: 338959-30-1
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: KVSPNWILRSCUBM-UHFFFAOYSA-N

物化性质

• 沸点：
  471.4±45.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzylindoline-6-carboxylic acid 、 氨基乙醛缩二甲醇 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 16.0h， 以99%的产率得到1-benzylindoline-6-carboxylic acid (2,2-dimethoxyethyl)amide
  参考文献：
  名称：

  ISOQUINOLINE AND QUINAZOLINE DEIVATIVES HAVING A COMBINED 5HT1A, 5HT1B AND 5HT1D RECEPTOR ACTIVITY

  摘要：

  公开号：

  EP1228043B1
• 作为产物：
  描述：

  6-吲哚甲酸 在 sodium hydroxide 、 sodium hydride 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 为溶剂， 生成 1-benzylindoline-6-carboxylic acid
  参考文献：
  名称：

  8-Piperazinyl-2,3-dihydropyrrolo[3,2-g]isoquinolines: Potent, selective, orally bioavailable 5-HT1 receptor ligands

  摘要：

  The novel 8-piperazinyl-2,3-dihydropyrroloisoquinoline template was synthesized in nine steps. The template was N-substituted to give a series of compounds showing binding to human cloned 5-HT1A, 5-HT1B and 5-HT1D receptors with pK(i)'s greater than 9 and selectivities up to 1000-fold against other serotonin, dopamine and adrenergic receptors. Several compounds were shown to possess weak partial agonist activity in cloned receptors, which translated to antagonism in in vitro studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.042

文献信息

• Isoquinoline and quinazoline derivatives having a combined 5HT1A, 5HT1B, and 5HT1D receptor activity
  申请人：Gaster Mary Laramie

  公开号：US20050239797A1

  公开（公告）日：2005-10-27

  The invention relates to novel isoquinoline and quinazoline derivatives having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of various disorders.

  本发明涉及具有药理活性的新异喹啉和喹唑啉衍生物，其制备方法，含有它们的组合物以及它们在治疗各种疾病中的应用。
• [EN] ISOQUINOLINE AND QUINAZOLINE DERIVATIVES HAVING A COMBINED 5HT1A, 5HT1B AND 5HT1D RECEPTOR ACTIVITY<br/>[FR] DERIVES D'ISOQUINOLINE ET DE QUINAZOLINE DOTES D'UNE ACTIVITE COMBINEE DE RECEPTEUR 5HT1A, 5HT1B ET 5HT1D
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2001032626A1

  公开（公告）日：2001-05-10

  The invention relates to novel isoquinoline and quinazoline derivatives of formula (I) having 5HT1A, 5HT1B and 5HT1D receptor affinity, processes for their preparation, to compositions containing them and to their use in the treatment of various disorders in which R1 is selected from a group of formula (i) where P1 is phenyl, naphthyl, a 5 or 6 membered heteroaryl ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulphur, a benzofused heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulphur, or a pyridofused heterocyclic ring containing 1 to 3 nitrogen atoms; Ra is halogen, C¿1-6?alkyl, C3-6cycloyalkyl, CF3, C1-6alkoxy, OCF3, hydroxy, cyano, nitro, hydroxyC1-6alkyl, COC1-6alkyl, CO2R?5, SO¿2R?5, NR5R6, CONR5R6¿, and SO¿2NR?5R6 where R?5 and R6¿ are independently hydrogen or C¿1-6?alkyl; n is 0,1,2 or 3; or group of formula (ii) in which P?2 and P3¿ are independently as defined for P1 above; R?b and Rc¿ are independently as defined for Ra above; p and q are independently as defined for n above; L is a single bond or NH; R2 is hydrogen or together with the group R3 forms a further group -CH = CH- or (CR7R8)2 where R?7 and R8¿ are independently hydrogen or C¿1-6?alkyl; R?3¿ is hydrogen or together with R2 forms a further group as defined above; Y is N or CH; X is N or CH; R4 is hydrogen or C¿1-6?alkyl.
• 8-Piperazinyl-2,3-dihydropyrrolo[3,2-g]isoquinolines: Potent, selective, orally bioavailable 5-HT1 receptor ligands
  作者：Tom D. Heightman、Laramie M. Gaster、Sarah L. Pardoe、Jean-Pierre Pilleux、Michael S. Hadley、Derek N. Middlemiss、Gary W. Price、Claire Roberts、Claire M. Scott、Jeannette M. Watson、Laurie J. Gordon、Vicky A. Holland、Jenifer Powles、Graham J. Riley、Tania O. Stean、Brenda K. Trail、Neil Upton、Nigel E. Austin、Andrew D. Ayrton、Tanya Coleman、Leanne Cutler

  DOI：10.1016/j.bmcl.2005.06.042

  日期：2005.10

  The novel 8-piperazinyl-2,3-dihydropyrroloisoquinoline template was synthesized in nine steps. The template was N-substituted to give a series of compounds showing binding to human cloned 5-HT1A, 5-HT1B and 5-HT1D receptors with pK(i)'s greater than 9 and selectivities up to 1000-fold against other serotonin, dopamine and adrenergic receptors. Several compounds were shown to possess weak partial agonist activity in cloned receptors, which translated to antagonism in in vitro studies. (c) 2005 Elsevier Ltd. All rights reserved.
• ISOQUINOLINE AND QUINAZOLINE DEIVATIVES HAVING A COMBINED 5HT1A, 5HT1B AND 5HT1D RECEPTOR ACTIVITY
  申请人：SmithKline Beecham plc

  公开号：EP1228043B1

  公开（公告）日：2005-01-12