3,5-dimethyl-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>benzonitrile | 126225-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-dimethyl-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>benzonitrile
• 英文别名: 5-[5-(2,6-dimethyl-4-cyanophenoxy)pentyl]-3-methylisoxazole；3,5-dimethyl-4-[5-(3-methyl-1,2-oxazol-5-yl)pentoxy]benzonitrile
• CAS: 126225-61-4
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: GCOSYSFBQJGMAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>benzonitrile 在 sodium azide 、 potassium carbonate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 73.0h， 生成 5-{5-[2,6-dimethyl-4-(2-methoxycarbonylmethyl-2H-tetrazol-5-yl)phenoxy]pentyl}-3-methylisoxazole
  参考文献：
  名称：

  Antipicornavirus activity of tetrazole analogs related to disoxaril

  摘要：

  A series of tetrazole analogues of Win 54954, a broad-spectrum antipicornavirus compound, has been synthesized to address the acid lability of the oxazoline ring of this series of compounds. The results of X-ray crystallography studies of several members of the oxazoline series bound to human rhinovirus type IA and 14 have been used to design compounds in the tetrazole series with a broad spectrum of activity. Compound 16b, which has a three-carbon linkage between the isoxazole and phenyl rings and a propyl chain extending from the isoxazole ring, exhibiting an MIC80 for 15 rhinovirus serotypes of 0.20 muM as compared to 0.40 muM for Win 54954. X-ray studies of 16b bound to human rhinovirus-14 show that the propyl side chain extends into a pore in the binding site with the possibility of hydrophobic interactions with a pocket formed by Leu106 and a portion of Ser107.

  DOI：

  10.1021/jm00074a004
• 作为产物：
  描述：

  5-(5-溴戊基)-3-甲基异恶唑 在 盐酸羟胺 、 乙酸酐 、 potassium carbonate 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 18.0h， 生成 3,5-dimethyl-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>benzonitrile
  参考文献：
  名称：

  Antipicornavirus activity of tetrazole analogs related to disoxaril

  摘要：

  A series of tetrazole analogues of Win 54954, a broad-spectrum antipicornavirus compound, has been synthesized to address the acid lability of the oxazoline ring of this series of compounds. The results of X-ray crystallography studies of several members of the oxazoline series bound to human rhinovirus type IA and 14 have been used to design compounds in the tetrazole series with a broad spectrum of activity. Compound 16b, which has a three-carbon linkage between the isoxazole and phenyl rings and a propyl chain extending from the isoxazole ring, exhibiting an MIC80 for 15 rhinovirus serotypes of 0.20 muM as compared to 0.40 muM for Win 54954. X-ray studies of 16b bound to human rhinovirus-14 show that the propyl side chain extends into a pore in the binding site with the possibility of hydrophobic interactions with a pocket formed by Leu106 and a portion of Ser107.

  DOI：

  10.1021/jm00074a004

文献信息

• 1,2,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral
  申请人：Sterling Drug Inc.

  公开号：US05175178A1

  公开（公告）日：1992-12-29

  Compounds of the formulas ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms; R' is lower-alkyl or hydroxy-lower-alkyl of 1-5 carbon atoms; R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and R.sub.8 is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when R.sub.8 is hydrogen R' is hydroxy-lower-alkyl, are useful as antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  化学式为##STR1##的化合物，其中：Y是3-9个碳原子的烷基桥；R'为1-5个碳原子的低碳基或羟基低碳基；R.sub.1和R.sub.2为氢、卤素、低碳基、低碳氧基、硝基、低碳氧羰基或三氟甲基；R.sub.8为氢或1-5个碳原子的低碳基，但当R.sub.8为氢时，R'为羟基低碳基。这些化合物可用作抗病毒剂，特别是对抗多种鼻病毒菌株，包括脊髓灰质炎病毒。
• Heterocyclic substituted-phenoxyalkylisoxazoles as antiviral useful
  申请人：Sterling Drug Inc.

  公开号：US04857539A1

  公开（公告）日：1989-08-15

  Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms; Z is N or HC; R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl; R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and Het is selected from specified heterocyclic groups, are useful and antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  化合物的公式为##STR1##其中：Y是3-9个碳原子的烷基桥；Z是N或HC；R是氢或1-5个碳原子的低碳基，但当Z为N时，R是低碳基；R.sub.1和R.sub.2是氢、卤素、低碳基、低碳氧基、硝基、低碳氧羰基或三氟甲基；Het是从指定的杂环基团中选择的，它们是有用的抗病毒剂，特别是对抗小肠病毒，包括许多鼻病毒菌株。
• Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0413289A2

  公开（公告）日：1991-02-20

  Compounds of the formulas wherein: Y is an alkylene bridge of 3-9 carbon atoms; R′ is lower-alkyl or hydroxy-lower-alkyl of 1-5 carbon atoms; R₁ and R₂ are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and R₈ is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when R₈ is hydrogen R′ is hydroxy-­lower-alkyl, are useful as antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  分子式如下的化合物 其中 Y 是 3-9 个碳原子的烯桥； R′ 是 1-5 个碳原子的低级烷基或羟基低级烷基； R₁ 和 R₂ 是氢、卤素、低级烷基、低级烷氧基、硝基、低级烷氧羰基或三氟甲基；以及 R₈ 是氢或 1-5 个碳原子的低级烷基，但当 R₈ 是氢时，R′ 是羟基-低级烷基、 可用作抗病毒剂，尤其是抗皮卡病毒，包括多种鼻病毒。
• US4857539A
  申请人：——

  公开号：US4857539A

  公开（公告）日：1989-08-15
• US4942241A
  申请人：——

  公开号：US4942241A

  公开（公告）日：1990-07-17