tert-butyl [5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]acetate | 1227199-94-1

• 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: tert-butyl [5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]acetate
• 英文别名: tert-butyl[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]acetate；tert-butyl 2-[5-(4-bromophenyl)imidazo[1,2-b]isoindol-5-yl]acetate
• CAS: 1227199-94-1
• 化学式: C₂₂H₂₁BrN₂O₂
• 分子量: 425.325
• InChiKey: AUGCCHBKQARVAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl [5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]acetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2-[5-(4-Bromophenyl)imidazo[1,2-b]isoindol-5-yl]acetic acid
  参考文献：
  名称：

  Tricyclic imidazole antagonists of the Neuropeptide S Receptor

  摘要：

  A new structural class of potent antagonists of the Neuropeptide S Receptor (NPSR) is reported. High-throughput screening identified a tricyclic imidazole antagonist of NPSR, and medicinal chemistry optimization of this structure was undertaken to improve potency against the receptor as well as CNS penetration. Detailed herein are synthetic and medicinal chemistry studies that led to the identification of antagonists 15 and NPSR-PI1, which demonstrate potent in vitro NPSR antagonism and central exposure in vivo. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.016
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole 在 氯化铵 、 乙酸乙酯 、 Sodium sulfate-III 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 1.58h， 生成 tert-butyl [5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]acetate
  参考文献：
  名称：

  Imidazoisoindole neuropeptide S receptor antagonists

  摘要：

  本发明涉及咪唑异异喹啉化合物，其为神经肽S受体拮抗剂，可用于治疗或预防神经系统和精神疾病，以及与神经肽S受体有关的疾病。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗神经肽S受体相关疾病中的使用。

  公开号：

  US08541595B2

文献信息

• [EN] IMIDAZOISOINDOLE NEUROPEPTIDE S RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES IMIDAZOISOINDOLES DES RÉCEPTEURS DU NEUROPEPTIDE S
  申请人：MERCK SHARP & DOHME

  公开号：WO2010056567A1

  公开（公告）日：2010-05-20

  The present invention is directed to imidazoisoindole compounds which are antagonists of neuropeptide S receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which the neuropeptide S receptor is involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the neuropeptide S receptor is involved.

  本发明涉及嘌呤并异噁唑烷酮类化合物，这些化合物是神经肽S受体拮抗剂，可用于治疗或预防涉及神经肽S受体的神经和精神疾病。该发明还涉及含有这些化合物的药物组合物以及这些化合物和组合物在预防或治疗涉及神经肽S受体的疾病中的用途。
• Imidazoisoindole Neuropeptide S Receptor Antagonists
  申请人：Manley Peter J.

  公开号：US20110212941A1

  公开（公告）日：2011-09-01

  The present invention is directed to imidazoisoindole compounds which are antagonists of neuropeptide S receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which the neuropeptide S receptor is involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the neuropeptide S receptor is involved.

  本发明涉及咪唑异异吲哚化合物，其为神经肽S受体的拮抗剂，并且在预防或治疗涉及神经肽S受体的神经和精神障碍和疾病方面是有用的。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗涉及神经肽S受体的这种疾病方面使用这些化合物和组合物。
• Imidazoisoindole neuropeptide S receptor antagonists
  申请人：Manley Peter J.

  公开号：US08541595B2

  公开（公告）日：2013-09-24

  The present invention is directed to imidazoisoindole compounds which are antagonists of neuropeptide S receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which the neuropeptide S receptor is involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the neuropeptide S receptor is involved.

  本发明涉及咪唑异异喹啉化合物，其为神经肽S受体拮抗剂，可用于治疗或预防神经系统和精神疾病，以及与神经肽S受体有关的疾病。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗神经肽S受体相关疾病中的使用。
• US8541595B2
  申请人：——

  公开号：US8541595B2

  公开（公告）日：2013-09-24
• Tricyclic imidazole antagonists of the Neuropeptide S Receptor
  作者：B. Wesley Trotter、Kausik K. Nanda、Peter J. Manley、Victor N. Uebele、Cindra L. Condra、Anthony L. Gotter、Karsten Menzel、Martin Henault、Rino Stocco、John J. Renger、George D. Hartman、Mark T. Bilodeau

  DOI：10.1016/j.bmcl.2010.04.016

  日期：2010.8

  A new structural class of potent antagonists of the Neuropeptide S Receptor (NPSR) is reported. High-throughput screening identified a tricyclic imidazole antagonist of NPSR, and medicinal chemistry optimization of this structure was undertaken to improve potency against the receptor as well as CNS penetration. Detailed herein are synthetic and medicinal chemistry studies that led to the identification of antagonists 15 and NPSR-PI1, which demonstrate potent in vitro NPSR antagonism and central exposure in vivo. (C) 2010 Elsevier Ltd. All rights reserved.