4-Anisyl-3,5-dimethylisoxazol | 30081-94-8

• 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: 4-Anisyl-3,5-dimethylisoxazol
• 英文别名: 4-(4-methoxy-phenylazo)-3,5-dimethyl-isoxazole；4-[(4-Methoxyphenyl)diazenyl]-3,5-dimethylisoxazole；(3,5-dimethyl-1,2-oxazol-4-yl)-(4-methoxyphenyl)diazene
• CAS: 30081-94-8
• 化学式: C₁₂H₁₃N₃O₂
• 分子量: 231.254
• InChiKey: GQZVEJORSBYZAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Anisyl-3,5-dimethylisoxazol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以70 %的产率得到
  参考文献：
  名称：

  Photoisomerization and Light‐Controlled Antibacterial Activity of Fluoroquinolone‐Azoisoxazole Hybrids

  摘要：

  Photopharmacology holds a huge untapped potential to locally treat diseases involving photoswitchable drugs via the elimination of drugs’ off‐target effects. The growth of this field has created a pressing demand to develop such light‐active drugs. We explored the potential for creating photoswitchable antibiotic hybrids by attaching pharmacophores norfloxacin/ciprofloxacin and azoisoxazole (photoswitch). All compounds exhibited a moderate to a high degree of bidirectional photoisomerization, long thermal cis half‐lives, and impressive photoresistance. Gram‐negative pathogens were found to be insensitive to these hybrids, while against Gram‐positive pathogens, all hybrids in their trans states exhibited antibacterial activity that is comparable to that of the parent drugs. Notably, the toxicity of the irradiated hybrid 6 was found to be 2‐fold lower than the nonirradiated trans isomer, indicating that the pre‐inactivated cis‐enriched drug can be employed for the site‐specific treatment of bacterial infection using light, which could potentially eliminate the unwanted exposure of toxic antibiotics to both beneficial and untargeted harmful microbes in our body. Molecular docking revealed different binding affinity of the cis and trans isomers with the topoisomerase IV enzyme, due to their different shapes.

  DOI：

  10.1002/cbic.202300851
• 作为产物：
  描述：

  3-(4-Methoxy-benzolazo)-acetylaceton 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 生成 4-Anisyl-3,5-dimethylisoxazol
  参考文献：
  名称：

  Garg,H.G., Journal of the Indian Chemical Society, 1963, vol. 40, p. 135 - 136

  摘要：

  DOI：

文献信息

• Potential antidiabetics. VI. 3-Methyl-4-arylhydrazono-2-isoxazolin-5-ones and 3-methyl-4-arylazo-5-(methyl phenyl)isoxazoles
  作者：Hari G. Garg、Prem Pal Singh

  DOI：10.1021/jm00300a070

  日期：1970.11
• Studies in the isoxazole series
  作者：S. D. Sokolov、S. M. Vinogradova

  DOI：10.1007/bf00473837

  日期：1979.9
• [EN] REVERSIBLE, OPTICALLY SWITCHABLE ADHESIVES BASED ON ARYLAZO-3,5-DIMETHYLISOXAZOLE DERIVATIVES<br/>[FR] ADHÉSIFS COMMUTABLES OPTIQUEMENT RÉVERSIBLES À BASE DE DÉRIVÉS D'ARYLAZO-3,5-DIMÉTHYLISOXAZOLE<br/>[DE] REVERSIBEL, OPTISCH SCHALTBARE KLEBSTOFFE AUF BASIS VON ARYLAZO-3,5-DIMETHYLISOXAZOL-DERIVATEN
  申请人：UNIV MUENSTER WESTFAELISCHE WILHELMS

  公开号：WO2021122175A1

  公开（公告）日：2021-06-24

  Die vorliegende Erfindung betrifft einen optisch schaltbaren Klebstoff, umfassend ein oder mehrere Arylazo-3,5-dimethylisoxazol-Derivate nach der folgenden Formel I: (I) wobei die Reste R1 bis R3 unabhängig voneinander ausgesucht sind aus der Gruppe bestehend aus H, F, Cl, Br, I und Alkoxy- oder Estergruppen mit einer unsubstituierten oder partiell- oder per-fluorierten, verzweigten oder unverzweigten C2-C20 Alkylkette, wobei mindestens einer der Reste R1 bis R3 eine Alkoxy- oder Estergruppe ist; die Reste R4 – R5 unabhängig voneinander ausgesucht sind aus der Gruppe bestehend aus H, C1-C3 Alkyl oder halogeniertes C1-C3 Alkyl; und die X und X' unabhängig voneinander ausgesucht sind aus der Gruppe bestehend aus H, F, Cl, Br und I. Des Weiteren betrifft die vorliegende Erfindung ein Verfahren zum reversiblen, optisch schaltbaren Aneinanderfügen von Werkstücken sowie die Verwendung der erfindungsgemäßen optischen Klebstoffe zum reversiblen Aneinanderfügen von Werkstücken.
• Garg,H.G., Journal of the Indian Chemical Society, 1963, vol. 40, p. 135 - 136
  作者：Garg,H.G.

  DOI：——

  日期：——
• Photoisomerization and Light‐Controlled Antibacterial Activity of Fluoroquinolone‐Azoisoxazole Hybrids
  作者：Anirban Dolai、Supriya Bhunia、Santosh Kumar Jana、Satyajit Bera、Sukhendu Mandal、Subhas Samanta

  DOI：10.1002/cbic.202300851

  日期：2024.4.16

  Photopharmacology holds a huge untapped potential to locally treat diseases involving photoswitchable drugs via the elimination of drugs’ off‐target effects. The growth of this field has created a pressing demand to develop such light‐active drugs. We explored the potential for creating photoswitchable antibiotic hybrids by attaching pharmacophores norfloxacin/ciprofloxacin and azoisoxazole (photoswitch). All compounds exhibited a moderate to a high degree of bidirectional photoisomerization, long thermal cis half‐lives, and impressive photoresistance. Gram‐negative pathogens were found to be insensitive to these hybrids, while against Gram‐positive pathogens, all hybrids in their trans states exhibited antibacterial activity that is comparable to that of the parent drugs. Notably, the toxicity of the irradiated hybrid 6 was found to be 2‐fold lower than the nonirradiated trans isomer, indicating that the pre‐inactivated cis‐enriched drug can be employed for the site‐specific treatment of bacterial infection using light, which could potentially eliminate the unwanted exposure of toxic antibiotics to both beneficial and untargeted harmful microbes in our body. Molecular docking revealed different binding affinity of the cis and trans isomers with the topoisomerase IV enzyme, due to their different shapes.