2H-茚并[5,6-d]噁唑-2,7(3H)-二酮,5,6-二氢-5-苯基- | 140384-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 2H-茚并[5,6-d]噁唑-2,7(3H)-二酮,5,6-二氢-5-苯基-
• 英文名称: 2,7-dioxo-5-phenylcyclopenta-2,3-dihydro<1,3>benzoxazole
• 英文别名: 2,3-dihydro-2,7-dioxo-5-phenylcyclopenta(f)benzoxazol；5-phenyl-5,6-dihydro-3H-cyclopenta[f][1,3]benzoxazole-2,7-dione
• CAS: 140384-37-8
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: XCTPBPWVGKUPFE-UHFFFAOYSA-N

物化性质

• 密度：
  1.382±0.06 g/cm3(Predicted)

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：
  0.12
• 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：

  2H-茚并[5,6-d]噁唑-2,7(3H)-二酮,5,6-二氢-5-苯基- 在 三乙基硅烷 、 sodium ethanolate 、 三氟乙酸 作用下， 反应 73.25h， 生成 5-phenyl-3-[3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propyl]-6,7-dihydro-5H-cyclopenta[f][1,3]benzoxazol-2-one
  参考文献：
  名称：

  Deoreux, Patrick; Aichaoui, Hocine; Lesieur, Isabelle, Heterocycles, 1993, vol. 36, # 5, p. 1051 - 1058

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯并唑啉酮 在 aluminum (III) chloride 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 2H-茚并[5,6-d]噁唑-2,7(3H)-二酮,5,6-二氢-5-苯基-
  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。
• Aichaoui, Hocine; Poupaert, Jacques H.; Lesieur, Daniel, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 12, p. 1053 - 1060
  作者：Aichaoui, Hocine、Poupaert, Jacques H.、Lesieur, Daniel、Henichart, Jean-Pierre

  DOI：——

  日期：——