9b-(4-methoxy-phenyl)-1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one | 5983-82-4

• 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-methoxy-phenyl)-1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one
• 英文别名: 9b-<4-Methoxy-phenyl>-1,2,3,9b-tetrahydro-5H-imidazo<2,1-a>isoindol-5-on；9b-(p-Methoxyphenyl)-1,2,3,9b-tetrahydro-5H-imidazo<2,1-a>isoindol-5-on；9b-(4-methoxyphenyl)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one；9b-(4-methoxyphenyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5-one
• CAS: 5983-82-4
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: KDWCKGOSODDQET-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  464.7±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)
• 溶解度：
  >42 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二氟苯甲酰氯 、 9b-(4-methoxy-phenyl)-1,2,3,9b-tetrahydro-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 0.5h， 生成 1-(3,4-Difluorobenzoyl)-9b-(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one
  参考文献：
  名称：

  Further optimization of the M5 NAM MLPCN probe ML375: Tactics and challenges

  摘要：

  This Letter describes the continued optimization of the MLPCN probe ML375, a highly selective M-5 negative allosteric modulator (NAM), through a combination of matrix libraries and iterative parallel synthesis. True to certain allosteric ligands, SAR was shallow, and the matrix library approach highlighted the challenges with M-5 NAM SAR within in this chemotype. Once again, enantiospecific activity was noted, and potency at rat and human M-5 were improved over ML375, along with slight enhancement in physiochemical properties, certain in vitro DMPK parameters and CNS distribution. Attempts to further enhance pharmacokinetics with deuterium incorporation afforded mixed results, but pretreatment with a pan-P450 inhibitor (1-aminobenzotriazole; ABT) provided increased plasma exposure. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.082
• 作为产物：
  描述：

  2-(4-甲氧基苯甲酰基)苯甲酸 、 乙二胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 9b-(4-methoxy-phenyl)-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

• [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。
• AEBERLI P.; EDEN P.; GOGERTY J. H.; HOULIHAN W. J.; PENBERTHY C., J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 2, 177-182
  作者：AEBERLI P.、 EDEN P.、 GOGERTY J. H.、 HOULIHAN W. J.、 PENBERTHY C.

  DOI：——

  日期：——
• US3994920A
  申请人：——

  公开号：US3994920A

  公开（公告）日：1976-11-30