3-(4-methoxyphenyl)-5-(4-nitrophenyl)isoxazole | 146918-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-methoxyphenyl)-5-(4-nitrophenyl)isoxazole
• 英文别名: 3-(4-Methoxyphenyl)-5-(4-nitrophenyl)-1,2-oxazole
• CAS: 146918-35-6
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: BLMXMHISOLYJNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  190-192 °C(Solv: ethanol (64-17-5))
• 沸点：
  498.7±40.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-5-(4-nitrophenyl)isoxazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以95%的产率得到4-(5-(4-nitrophenyl)isoxazol-3-yl)phenol
  参考文献：
  名称：

  Antiproliferative novel isoxazoles: Modeling, virtual screening, synthesis, and bioactivity evaluation

  摘要：

  A series of novel isoxazole derivatives were efficiently synthesized through the adaptation/modification of an in situ synthetic procedure for pyrazoles. All novel compounds were tested against four different cell lines to evaluate their antiproliferative activity. Based on the Hela cells results of this study and previous work, a classification model to predict the anti-proliferative activity of isoxazole and pyrazole derivatives was developed. Random Forest modeling was used in view of the development of an accurate and reliable model that was subsequently validated. A virtual screening study was then proposed for the design of novel active derivatives. Compounds 9 and 11 demonstrated significant cytostatic activity; the fused isoxazole derivative 18 and the virtually proposed compound 2v, were proved at least 10 times more potent as compared to compound 9, with IC50 values near and below 1 mu M. In conclusion, a new series of isoxazoles was exploited with some of them exhibiting promising cytostatic activities. Further studies on the substitution pattern of the isoxazole core can potentially provide compounds with cytostatic action at the nM scale. In this direction the in silica approach described herein can also be used to screen existing databases to identify derivatives with anticipated activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.011
• 作为产物：
  描述：

  对甲氧基苯甲醛肟 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-methoxyphenyl)-5-(4-nitrophenyl)isoxazole
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 3,5-diarylisoxazoles and 3,5-diaryl-1,2,4-oxadiazoles, novel classes of small molecule interleukin-8 (IL-8) receptor antagonists

  摘要：

  A novel series of 3,5-diarylisoxazole and 3,5-diaryl-1,2,4-oxadiazole IL-8 antagonists has been identified. These compounds exhibit activity in an IL-8 binding assay as well as in a functional assay of IL-8 induced elastase release from neutrophils. In addition, one of the compounds exhibits oral activity in a rat adjuvant arthritis model. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.080

文献信息

• Synthesis of 3,5-diarylisoxazoles under solvent-free conditions using iodobenzene diacetate
  作者：Kondapalli Venkata Gowri Chandra Sekhar、Thripuraribhatla Venkata Naga Varun Sasank、Hunsur Nagendra Nagesh、Narva Suresh、Kalaga Mahalakshmi Naidu、Amaroju Suresh

  DOI：10.1016/j.cclet.2013.07.022

  日期：2013.12

  Abstract A simple and efficient method has been developed for conversion of chalcone oximes to 3,5-diaryl isoxazoles in excellent yields under solvent-free conditions. The synthesized compounds were characterized by infrared spectroscopy, 1 H NMR, 13 C NMR and HRMS.

  摘要研究了一种简单有效的方法，可在无溶剂条件下以优异的收率将查尔酮肟转化为3,5-二芳基异恶唑。合成的化合物通过红外光谱，1 H NMR，13 C NMR和HRMS进行表征。
• Bandiera, T.; Gruenanger, P.; Albini, F. Marinone, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 6, p. 1423 - 1428
  作者：Bandiera, T.、Gruenanger, P.、Albini, F. Marinone

  DOI：——

  日期：——
• Bandiera T., Gruenanger P., Albini F. Marinone, J. Heterocycl. Chem., 29 (1992) N 6, S 1423-1428
  作者：Bandiera T., Gruenanger P., Albini F. Marinone

  DOI：——

  日期：——
• Synthesis and structure–activity relationships of 3,5-diarylisoxazoles and 3,5-diaryl-1,2,4-oxadiazoles, novel classes of small molecule interleukin-8 (IL-8) receptor antagonists
  作者：Michele A Weidner-Wells、Todd C Henninger、Stephanie A Fraga-Spano、Christine M Boggs、Michele Matheis、David M Ritchie、Dennis C Argentieri、Michael P Wachter、Dennis J Hlasta

  DOI：10.1016/j.bmcl.2004.05.080

  日期：2004.8

  A novel series of 3,5-diarylisoxazole and 3,5-diaryl-1,2,4-oxadiazole IL-8 antagonists has been identified. These compounds exhibit activity in an IL-8 binding assay as well as in a functional assay of IL-8 induced elastase release from neutrophils. In addition, one of the compounds exhibits oral activity in a rat adjuvant arthritis model. (C) 2004 Elsevier Ltd. All rights reserved.
• Antiproliferative novel isoxazoles: Modeling, virtual screening, synthesis, and bioactivity evaluation
  作者：Evangelia Tzanetou、Sandra Liekens、Konstantinos M. Kasiotis、Georgia Melagraki、Antreas Afantitis、Nikolas Fokialakis、Serkos A. Haroutounian

  DOI：10.1016/j.ejmech.2014.05.011

  日期：2014.6

  A series of novel isoxazole derivatives were efficiently synthesized through the adaptation/modification of an in situ synthetic procedure for pyrazoles. All novel compounds were tested against four different cell lines to evaluate their antiproliferative activity. Based on the Hela cells results of this study and previous work, a classification model to predict the anti-proliferative activity of isoxazole and pyrazole derivatives was developed. Random Forest modeling was used in view of the development of an accurate and reliable model that was subsequently validated. A virtual screening study was then proposed for the design of novel active derivatives. Compounds 9 and 11 demonstrated significant cytostatic activity; the fused isoxazole derivative 18 and the virtually proposed compound 2v, were proved at least 10 times more potent as compared to compound 9, with IC50 values near and below 1 mu M. In conclusion, a new series of isoxazoles was exploited with some of them exhibiting promising cytostatic activities. Further studies on the substitution pattern of the isoxazole core can potentially provide compounds with cytostatic action at the nM scale. In this direction the in silica approach described herein can also be used to screen existing databases to identify derivatives with anticipated activity. (C) 2014 Elsevier Masson SAS. All rights reserved.