9b-(4-fluorophenyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-one | 5964-48-7

• 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-(4-fluorophenyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-one
• 英文别名: 9b-(4-fluoro-phenyl)-1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one；9b-(p-fluorophenyl)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one；9b-<4-Fluor-phenyl>-1,2,3,9b-tetrahydro-5H-imidazo<2,1-a>isoindol-5-on；9b-(4-fluorophenyl)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one；9b-(4-fluorophenyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5-one
• CAS: 5964-48-7
• 化学式: C₁₆H₁₃FN₂O
• 分子量: 268.29
• InChiKey: HDPOBIOWQBVXAS-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190 °C
• 沸点：
  428.5±45.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 溶解度：
  >40.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9b-(4-fluorophenyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-one 生成 2,3-二氢-5-(4-氟苯基)-5H-咪唑并[2,1-a]异吲哚-5-醇
  参考文献：
  名称：

  AEBERLI P.; EDEN P.; GOGERTY J. H.; HOULIHAN W. J.; PENBERTHY C., J. MED. CHEM. , 1975, 18, NO 2, 177-182

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-氟苯酰基)苯甲酸 、 乙二胺 以to obtain 9b-(p-fluorophenyl)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one的产率得到9b-(4-fluorophenyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-one
  参考文献：
  名称：

  5H-imidazo[2,1-a]isoindol-5-one compounds

  摘要：

  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。

  公开号：

  US03994920A1

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- 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- 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- 等，(R1)可以是苯基及其取代形式，(R2)可以是各种取代基。
• 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
  作者：Silas Bond、Alistair G. Draffan、Jennifer E. Fenner、John Lambert、Chin Yu Lim、Bo Lin、Angela Luttick、Jeffrey P. Mitchell、Craig J. Morton、Roland H. Nearn、Vanessa Sanford、Pauline C. Stanislawski、Simon P. Tucker

  DOI：10.1016/j.bmcl.2014.11.018

  日期：2015.2

  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.
• Discovery of the First M₅-Selective and CNS Penetrant Negative Allosteric Modulator (NAM) of a Muscarinic Acetylcholine Receptor: (<i>S</i>)-9b-(4-Chlorophenyl)-1-(3,4-difluorobenzoyl)-2,3-dihydro-1<i>H</i>-imidazo[2,1-<i>a</i>]isoindol-5(9b<i>H</i>)-one (ML375)
  作者：Patrick R. Gentry、Masaya Kokubo、Thomas M. Bridges、Nathan R. Kett、Joel M. Harp、Hyekyung P. Cho、Emery Smith、Peter Chase、Peter S. Hodder、Colleen M. Niswender、J. Scott Daniels、P. Jeffrey Conn、Michael R. Wood、Craig W. Lindsley

  DOI：10.1021/jm4013246

  日期：2013.11.27

  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.