5-(4-chlorophenyl)-3H-indano[5,6-d]oxazol-2,7-dione | 483287-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-(4-chlorophenyl)-3H-indano[5,6-d]oxazol-2,7-dione
• 英文别名: 5-(4-chlorophenyl)-5,6-dihydro-3H-cyclopenta[f][1,3]benzoxazole-2,7-dione
• CAS: 483287-97-4
• 化学式: C₁₆H₁₀ClNO₃
• 分子量: 299.713
• InChiKey: YUUIPBPYXZZACH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-3H-indano[5,6-d]oxazol-2,7-dione 在 溴 、 三乙胺 作用下， 以 氯仿 、 溶剂黄146 、 丙酮 为溶剂， 反应 24.0h， 生成 5-(4-chlorophenyl)-3H-indeno[5,6-d]oxazol-2,7-dione
  参考文献：
  名称：

  Investigations of new lead structures for the design of novel cyclooxygenase-2 inhibitors

  摘要：

  On the basis of molecular modelling studies, five new compounds were synthesised and studied in an attempt to design new lead structures as selective COX-2 inhibitors. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01373-9
• 作为产物：
  描述：

  6-乙酰基-2(3H)-苯唑酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 17.0h， 生成 5-(4-chlorophenyl)-3H-indano[5,6-d]oxazol-2,7-dione
  参考文献：
  名称：

  Carboline- and phenothiazine-derivated heterocycles as potent SIGMA-1 protein ligands

  摘要：

  Sigma 1 receptors are associated with neurodegenerative and psychiatric disorders. These receptors, via their chaperoning functions that counteract endoplasmic reticulum stress and block neurodegeneration, may serve as a target for a new generation of antidepressants or neuroprotective agents. The involvement of these receptors has also been observed in neuropathic pain and cancer. Only a few ligands, such as Igmesine and Anavex 2-73, have been involved in clinical trials. Thus the development of sigma 1 ligands is of interest to a new generation of drugs. Previous work in our lab underlined the potency of benzannulated bicyclic compounds as interesting ligands. Herein the work was extended to a series of novel tricyclic compounds. Carboline- and phenothiazine-derivated compounds were designed and synthesized. In vitro competition binding assays for sigma 1 and 2 receptors showed that most of them have high affinity for sigma 1 receptor (K-i = 2.5-18 nM), and selectivity toward sigma 2 receptor, without cytotoxic effects on SY5Y cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.053

文献信息

• Synthesis of 1,11-Dihydro-2H-[1,3]oxazolo[4′,5′:5,6]indeno[1,2-b]quinolin-2-ones with Potential Topoisomerase I Inhibitory Activity
  作者：Pascal Carato、Christophe Furman、Marc Delot、Amélie Lemoine、Nicolas Lebegue、Pascal Berthelot、Saïd Yous

  DOI：10.1055/s-0029-1217007

  日期：2009.11

  A series of 1,11-dihydro-2H-[1,3]oxazolo[4′,5′:5,6]indeno[1,2-b]quinolin-2-ones were prepared by means of Friedländer condensations. The starting materials for the preparations were commercial substituted-2-aminoacetophenones and various 5,6-dihydro-2H-indeno[5,6-d][1,3]oxazole-2,7(3H)-diones that were synthesized from 2(3H)-benzoxazolones or their N-methyl analogues.

  一系列1,11-二氢-2H-[1,3]噁唑[4′,5′:5,6]印地[n-2]喹啉-2-酮通过弗里德兰德缩合反应制备。反应的起始材料为商业化的取代-2-氨基乙酰苯酮和各种5,6-二氢-2H-印地[5,6-d][1,3]噁唑-2,7(3H)-二酮，这些化合物是从2(3H)-苯并噁唑酮或其N-甲基类似物合成的。
• Carboline- and phenothiazine-derivated heterocycles as potent SIGMA-1 protein ligands
  作者：Marion Donnier-Maréchal、Paul-Emmanuel Larchanché、Delphine Le Broc、Christophe Furman、Pascal Carato、Patricia Melnyk

  DOI：10.1016/j.ejmech.2014.10.053

  日期：2015.1

  Sigma 1 receptors are associated with neurodegenerative and psychiatric disorders. These receptors, via their chaperoning functions that counteract endoplasmic reticulum stress and block neurodegeneration, may serve as a target for a new generation of antidepressants or neuroprotective agents. The involvement of these receptors has also been observed in neuropathic pain and cancer. Only a few ligands, such as Igmesine and Anavex 2-73, have been involved in clinical trials. Thus the development of sigma 1 ligands is of interest to a new generation of drugs. Previous work in our lab underlined the potency of benzannulated bicyclic compounds as interesting ligands. Herein the work was extended to a series of novel tricyclic compounds. Carboline- and phenothiazine-derivated compounds were designed and synthesized. In vitro competition binding assays for sigma 1 and 2 receptors showed that most of them have high affinity for sigma 1 receptor (K-i = 2.5-18 nM), and selectivity toward sigma 2 receptor, without cytotoxic effects on SY5Y cells. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Investigations of new lead structures for the design of novel cyclooxygenase-2 inhibitors
  作者：Chang Ha Park、Xavier Siomboing、Saı̈d Yous、Bernard Gressier、Michel Luyckx、Philippe Chavatte

  DOI：10.1016/s0223-5234(02)01373-9

  日期：2002.6

  On the basis of molecular modelling studies, five new compounds were synthesised and studied in an attempt to design new lead structures as selective COX-2 inhibitors. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.