9b-(p-tolyl)-1,2,3,9b-tetrahydro-1H-imidazo[2,1-a]isoindol-5-one | 5983-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 9b-(p-tolyl)-1,2,3,9b-tetrahydro-1H-imidazo[2,1-a]isoindol-5-one
• 英文别名: 9b-(p-tolyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-one；9b-(p-tolyl)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one；9b-p-tolyl-1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one；1.2.3.9b-Tetrahyro-9b-(p-tolyl)-5H-imidazo<2,1-a>isoindol-5-on；9b-(4-methylphenyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5-one
• CAS: 5983-81-3
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: UQXIWIHDBAMLIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  3-(三氟甲基)苯甲酰氯 、 9b-(p-tolyl)-1,2,3,9b-tetrahydro-1H-imidazo[2,1-a]isoindol-5-one 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 9b-(4-Methylphenyl)-1-[3-(trifluoromethyl)benzoyl]-2,3-dihydroimidazo[2,1-a]isoindol-5-one
  参考文献：
  名称：

  Discovery of the First M₅-Selective and CNS Penetrant Negative Allosteric Modulator (NAM) of a Muscarinic Acetylcholine Receptor: (S)-9b-(4-Chlorophenyl)-1-(3,4-difluorobenzoyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-one (ML375)

  摘要：

  A functional high throughput screen and subsequent multidimensional, iterative parallel synthesis effort identified the first muscarinic acetylcholine receptor (mAChR) negative allosteric modulator (NAM) selective for the M-5 subtype. ML375 is a highly selective M-5 NAM with submicromolar potency (human M-5 IC50 = 300 nM, rat M-5 IC50 = 790 nM, M1-M4 IC50 > 30 mu M), excellent multispecies PK, high CNS penetration, and enantiospecific inhibition.

  DOI：

  10.1021/jm4013246
• 作为产物：
  描述：

  2-(4-甲基苯甲酰)苯甲酸 、 乙二胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 9b-(p-tolyl)-1,2,3,9b-tetrahydro-1H-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

• [EN] POLYCYCLIC AGENTS FOR THE TREATMENT OF RESPIRATORY SYNCYTIAL VIRUS INFECTIONS<br/>[FR] AGENTS POLYCYCLIQUES POUR LE TRAITEMENT D'INFECTIONS PAR LE VIRUS SYNCYTIAL RESPIRATOIRE
  申请人：BIOTA SCIENT MANAGEMENT

  公开号：WO2005061513A1

  公开（公告）日：2005-07-07

  Compounds of formula (I), and their use as in the treatment of infections involving viruses of the Pneumovirinae sub-family (RSV) are disclosed. In the formula ring (A) may be phenyl, pyridyl etc., (B-C) may be CH2-CH2 etc., (R1) may be phenyl and substituted forms thereof, (R2) may be assorted substituents.

  公式（I）的化合物及其在治疗涉及Pneumovirinae亚科病毒的感染中的用途已被披露。在该公式中，环（A）可以是苯基、吡啶基等，（B-C）可以是CH2-CH2等，（R1）可以是苯基及其取代形式，（R2）可以是各种取代基。
• Polycyclic agents for the treatment of respiratory syncytial virus infections
  申请人：Bond Silas

  公开号：US20070287700A1

  公开（公告）日：2007-12-13

  Compounds of formula (I), and their use as in the treatment of infections involving viruses of the Pneumovirinae sub-family (RSV) are disclosed. In the formula ring (A) may be phenyl, pyridyl etc., (B-C) may be CH 2 —CH 2 etc., (R 1 ) may be phenyl and substituted forms thereof, (R 2 ) may be assorted substituents.

  本发明公开了化学式(I)的化合物及其在治疗涉及Pneumovirinae亚科（RSV）病毒感染中的应用。在该式中，环（A）可以是苯基、吡啶基等，（B-C）可以是CH2-CH2等，（R1）可以是苯基及其取代形式，（R2）可以是不同的取代基。
• Polycyclic Agents for the Treatment of Respiratory Syncytial Virus Infections
  申请人：Biota Scientific Management Pty Ltd.

  公开号：US20140051689A1

  公开（公告）日：2014-02-20

  Compounds of formula (I), and their use as in the treatment of infections involving viruses of the Pneumovirinae sub-family (RSV) are disclosed. In the formula ring (A) may be phenyl, pyridyl etc., (B-C) may be CH 2 —CH 2 etc., (R 1 ) may be phenyl and substituted forms thereof, (R 2 ) may be assorted substituents.

  本发明涉及化合物(I)的公式及其在治疗涉及Pneumovirinae亚科病毒（RSV）感染方面的用途。在该公式中，环(A)可以是苯基、吡啶基等，(B-C)可以是CH2-CH2等，(R1)可以是苯基及其取代形式，(R2)可以是各种取代基。
• US3935218A
  申请人：——

  公开号：US3935218A

  公开（公告）日：1976-01-27
• US4058529A
  申请人：——

  公开号：US4058529A

  公开（公告）日：1977-11-15