1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one | 16780-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one
• 英文别名: 1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one；1,2,3,9b-tetrahydroimidazo[1,2-b]isoindol-5-one
• CAS: 16780-93-1
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: BHTOLNUCTNDTDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对氟苯甲酰氯 、 1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one 以 吡啶 为溶剂， 生成 1-(4-fluorobenzoyl)-3,9b-dihydro-2H-imidazo[1,2-b]isoindol-5-one
  参考文献：
  名称：

  The discovery of 1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones as a new class of respiratory syncytial virus (RSV) fusion inhibitors. Part 1

  摘要：

  Respiratory syncytial virus (RSV) is a major cause of respiratory tract infections in infants, young children and adults. Compound 1a (9b-(4-chlorophenyl)-1-(4-fluorobenzoyl)-1,2,3,9b-tetrahydro-5H-imidazo[ 2,1-a]isoindol-5-one) was identified as an inhibitor of A and B strains of RSV targeting the fusion glycoprotein. SAR was developed by systematic exploration of the phenyl (R-1) and benzoyl (R-2) groups. Furthermore, introduction of a nitrogen at the 8-position of the tricyclic core resulted in active analogues with improved properties (aqueous solubility, protein binding and logD) and excellent rat pharmacokinetics (e. g., rat oral bioavailability of 89% for compound 17). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.018
• 作为产物：
  描述：

  乙二胺 、 邻羧基苯甲醛 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one
  参考文献：
  名称：

  The discovery of 1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones as a new class of respiratory syncytial virus (RSV) fusion inhibitors. Part 1

  摘要：

  Respiratory syncytial virus (RSV) is a major cause of respiratory tract infections in infants, young children and adults. Compound 1a (9b-(4-chlorophenyl)-1-(4-fluorobenzoyl)-1,2,3,9b-tetrahydro-5H-imidazo[ 2,1-a]isoindol-5-one) was identified as an inhibitor of A and B strains of RSV targeting the fusion glycoprotein. SAR was developed by systematic exploration of the phenyl (R-1) and benzoyl (R-2) groups. Furthermore, introduction of a nitrogen at the 8-position of the tricyclic core resulted in active analogues with improved properties (aqueous solubility, protein binding and logD) and excellent rat pharmacokinetics (e. g., rat oral bioavailability of 89% for compound 17). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.018

文献信息

• 5H-imidazo[2,1-a]isoindol-5-one compounds
  申请人：American Home Products Corporation

  公开号：US03994920A1

  公开（公告）日：1976-11-30

  A new class of chemical compounds whose members exert an appetite suppressant and mood elevating effect in man has been invented. This class is defined as being composed of those compounds having the 1-substituted-2,5-benzodiazocine structure, fully saturated in the nonbenzenoid portion, and whose nitrogens are tervalent. Members of this class are prepared by condensing an orthobenzoylbenzoic acid or ester thereof with an ethylenediamine and reducing with a metallic alkaline hydride the product thus obtained.

  一种新的化合物类别已被发明，其成员在人体中具有食欲抑制和情绪提升的效果。该类别的定义为由具有1-取代-2,5-苯并二氮杂环结构的化合物组成，非苯环部分完全饱和，并且其氮原子为三价。该类别的成员通过将正交苯甲酰苯甲酸或其酯与乙二胺缩合，并用金属碱性氢化物还原所得产物制备而成。
• Synthesis of Isoindolinones by Palladium-Catalyzed Carbonylative Cyclization of 2-Bromobenzaldehyde with Diamines
  作者：C. S. Cho、L. H. Jiang、S. C. Shim

  DOI：10.1080/00032719808006483

  日期：1998.3.1

  2-Bromobenzaldehyde reacts with diamines under carbon monoxide in the presence of a catalytic amount of a palladium complex to afford the corresponding tricyclic isoindolinones in fair to good yields.
• US3931217A
  申请人：——

  公开号：US3931217A

  公开（公告）日：1976-01-06
• US3935218A
  申请人：——

  公开号：US3935218A

  公开（公告）日：1976-01-27
• US4018765A
  申请人：——

  公开号：US4018765A

  公开（公告）日：1977-04-19