3-carboxy-4-phenyl-1,2,5-oxadiazole 2-oxide | 125520-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-carboxy-4-phenyl-1,2,5-oxadiazole 2-oxide
• 英文别名: 2-oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-carboxylic acid
• CAS: 125520-55-0
• 化学式: C₉H₆N₂O₄
• 分子量: 206.158
• InChiKey: OSVBYKCDKUTGTN-UHFFFAOYSA-N

物化性质

• 沸点：
  404.9±37.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-carboxy-4-phenyl-1,2,5-oxadiazole 2-oxide 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 3.0h， 生成 3-(chlorocarbonyl)-4-phenyl-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Fruttero, Roberta; Ferrarotti, Bruno; Serafino, Anna, Liebigs Annalen der Chemie, 1990, # 4, p. 335 - 338

  摘要：

  DOI：
• 作为产物：
  描述：

  4-phenylfuroxan-3-carboxaldehyde 在 jones reagent 作用下， 生成 3-carboxy-4-phenyl-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Calvino; Di Stilo; Fruttero, Il Farmaco, 1993, vol. 48, # 2, p. 321 - 334

  摘要：

  DOI：

文献信息

• Design, Synthesis, and <i>in vitro</i> Evaluation of P2X7 Antagonists
  作者：Dimitra T. Pournara、Anna Durner、Eftichia Kritsi、Alexios Papakostas、Panagiotis Zoumpoulakis、Annette Nicke、Maria Koufaki

  DOI：10.1002/cmdc.202000303

  日期：2020.12.15

  is a promising target for the treatment of various diseases due to its significant role in inflammation and immune cell signaling. This work describes the design, synthesis, and in vitro evaluation of a series of novel derivatives bearing diverse scaffolds as potent P2X7 antagonists. Our approach was based on structural modifications of reported (adamantan‐1‐yl)methylbenzamides able to inhibit the receptor

  由于 P2X7 受体在炎症和免疫细胞信号传导中的重要作用，它是治疗各种疾病的有希望的靶点。这项工作描述了一系列带有多种支架的新型衍生物作为有效的 P2X7 拮抗剂的设计、合成和体外评估。我们的方法基于已报道的（金刚烷-1-基）甲基苯甲酰胺的结构修饰，能够抑制受体激活。金刚烷部分和酰胺键被替换，并通过基于配体的药效团模型评估替换。通过双电极电压钳实验评估合成类似物的拮抗效力，使用非洲爪蟾表达人 P2X7 受体的卵母细胞。SAR 研究表明，用芳基-环己基部分取代金刚烷环是对抗 P2X7 阳离子通道激活的最有效拮抗剂，类似物 2-氯-N- [1-(3-(硝基氧基甲基)苯基)环己基)甲基]苯甲酰胺 ( 56 ) 表现出最佳效力，IC 50值为 0.39 μM。
• Discovery of new orally effective analgesic and anti-inflammatory hybrid furoxanyl N-acylhydrazone derivatives
  作者：Paola Hernández、Mauricio Cabrera、María Laura Lavaggi、Laura Celano、Inés Tiscornia、Thiago Rodrigues da Costa、Leonor Thomson、Mariela Bollati-Fogolín、Ana Luisa P. Miranda、Lidia M. Lima、Eliezer J. Barreiro、Mercedes González、Hugo Cerecetto

  DOI：10.1016/j.bmc.2012.01.034

  日期：2012.3

  We report the design, the synthesis and the biological evaluation of the analgesic and anti-inflammatory activities of furoxanyl N-acylhydrazones (furoxanyl-NAH) by applying molecular hybridization approach. Hybrid compounds with IL-8-release inhibition capabilities were identified. Among them, furoxanyl-NAH, 17, and benzofuroxanyl-derivative, 24, together with furoxanyl-NAH derivative, 31, without IL-8 inhibition displayed both orally analgesic and anti-inflammatory activities. These hybrid derivatives do not have additional LOX- or COX-inhibition activities. For instance, LOX-inhibition by furoxanyl-NAH derivative, 42, emerged as a structural lead to develop new inhibitors. The lack of mutagenicity of the active derivatives 17, 31, and 42, allow us to propose them as candidates for further clinical studies. These results confirmed the success in the exploitation of hybridization strategy for identification of novel N-acylhydrazones (NAH) with optimized activities. (C) 2012 Elsevier Ltd. All rights reserved.
• Gasco, Andrea Marcello; Fruttero, Roberta; Sorba, Giovanni, Liebigs Annalen der Chemie, 1991, # 11, p. 1211 - 1213
  作者：Gasco, Andrea Marcello、Fruttero, Roberta、Sorba, Giovanni、Gasco, Alberto

  DOI：——

  日期：——
• FRUTTERO, ROBERTA;FERRAROTTI, BRUNO;SERAFINO, ANNA;GASCO, ALBERTO, LIEBIGS ANN. CHEM.,(1990) N, C. 335-338
  作者：FRUTTERO, ROBERTA、FERRAROTTI, BRUNO、SERAFINO, ANNA、GASCO, ALBERTO

  DOI：——

  日期：——
• Calvino; Di Stilo; Fruttero, Il Farmaco, 1993, vol. 48, # 2, p. 321 - 334
  作者：Calvino、Di Stilo、Fruttero、Gasco、Sorba、Gasco

  DOI：——

  日期：——

表征谱图