6-cinnamoylbenzo[d]oxazol-2(3H)-one | 54903-21-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 6-cinnamoylbenzo[d]oxazol-2(3H)-one
• 英文别名: 6-(3-phenyl-acryloyl)-3H-benzooxazol-2-one；6-Cinnamoylbenzoxazolinone；6-(3-phenylprop-2-enoyl)-3H-1,3-benzoxazol-2-one
• CAS: 54903-21-8
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: GMTCPBAANXMHHT-UHFFFAOYSA-N

物化性质

• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  6-cinnamoylbenzo[d]oxazol-2(3H)-one 在 三乙基硅烷 、 PPA 、 三氟乙酸 作用下， 反应 72.92h， 生成 2-oxo-5-phenylcyclopenta-2,3-dihydro<1,3>benzoxazole
  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 6.0h， 生成 6-cinnamoylbenzo[d]oxazol-2(3H)-one
  参考文献：
  名称：

  A Ratiometric Acoustogenic Probe for in Vivo Imaging of Endogenous Nitric Oxide

  摘要：

  Photoacoustic (PA) imaging is an emerging imaging modality that utilizes optical excitation and acoustic detection to enable high resolution at centimeter depths. The development of activatable PA probes can expand the utility of this technology to allow for detection of specific stimuli within live-animal models. Herein, we report the design, development, and evaluation of a series of Acoustogenic Probe(s) for Nitric Oxide (APNO) for the ratiometric, analyte-specific detection of nitric oxide (NO) in vivo. The best probe in the series, APNO-5, rapidly responds to NO to form an N-nitroso product with a concomitant 91 nm hypsochromic shift. This property enables ratiometric PA imaging upon selective irradiation of APNO-5 and the corresponding product, tAPNO-S. Moreover, APNO-5 displays the requisite photophysical characteristics for in vivo PA imaging (e.g., high absorptivity, low quantum yield) as well as high biocompatibility, stability, and selectivity for NO over a variety of biologically relevant analytes. APNO-5 was successfully applied to the detection of endogenous NO in a murine lipopolysaccharide-induced inflammation model. Our studies show a 1.9-fold increase in PA signal at 680 run and a 1.3-fold ratiometric turn-on relative to a saline control.

  DOI：

  10.1021/jacs.7b10783

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。
• Chalcones
  申请人：Adir et Compagnie

  公开号：US05179091A1

  公开（公告）日：1993-01-12

  Compounds of general formula (I): in which: ##STR1## R.sub.1, X, Y, Z, T, R.sub.2, R.sub.3 and R.sub.4 are defined in the description. Medicinal products.

  通式（I）的化合物：其中：##STR1## R.sub.1，X，Y，Z，T，R.sub.2，R.sub.3和R.sub.4在说明中定义。药品。
• Bonte; Lesieur; Lespagnol, European Journal of Medicinal Chemistry, 1974, vol. 9, # 5, p. 497 - 500
  作者：Bonte、Lesieur、Lespagnol、et al.

  DOI：——

  日期：——
• 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.
• Deoreux, Patrick; Aichaoui, Hocine; Lesieur, Isabelle, Heterocycles, 1993, vol. 36, # 5, p. 1051 - 1058
  作者：Deoreux, Patrick、Aichaoui, Hocine、Lesieur, Isabelle

  DOI：——

  日期：——