3,5-dichloro-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>benzonitrile | 107311-82-0

• 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: 3,5-dichloro-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>benzonitrile
• 英文别名: 5-[5-(2,6-dichloro-4-cyanophenoxy)pentyl]-3-methylisoxazole；3,5-dichloro-4-[5-(3-methyl-1,2-oxazol-5-yl)pentoxy]benzonitrile
• CAS: 107311-82-0
• 化学式: C₁₆H₁₆Cl₂N₂O₂
• 分子量: 339.221
• InChiKey: CVIWGBSJPQYEHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-dichloro-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>benzonitrile 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以62%的产率得到5-<3,5-dichloro-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>phenyl>-1H-tetrazole
  参考文献：
  名称：

  Antirhinoviral activity of heterocyclic analogs of Win 54954

  摘要：

  A variety of heterocyclic analogs of Win 54954 have been synthesized and tested in vitro against human rhinovirus type 14 (HRV-14) in a plaque reduction assay. The more active compounds were tested against 14 additional serotypes, and the concentration which inhibited 80% of the serotypes tested (MIC80) was measured. One compound, 37, exhibited activity comparable to Win 59454. Physicochemical as well as electrostatic parameters were calculated and the results subjected to a QSAR analysis in an effort to explain differences in activity observed between these compounds; however, no meaningful correlation with biological activity was found with any of these parameters.

  DOI：

  10.1021/jm00102a017
• 作为产物：
  描述：

  羟敌草腈 、 5-(5-溴戊基)-3-甲基异恶唑 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以48%的产率得到3,5-dichloro-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>benzonitrile
  参考文献：
  名称：

  Antirhinoviral activity of heterocyclic analogs of Win 54954

  摘要：

  A variety of heterocyclic analogs of Win 54954 have been synthesized and tested in vitro against human rhinovirus type 14 (HRV-14) in a plaque reduction assay. The more active compounds were tested against 14 additional serotypes, and the concentration which inhibited 80% of the serotypes tested (MIC80) was measured. One compound, 37, exhibited activity comparable to Win 59454. Physicochemical as well as electrostatic parameters were calculated and the results subjected to a QSAR analysis in an effort to explain differences in activity observed between these compounds; however, no meaningful correlation with biological activity was found with any of these parameters.

  DOI：

  10.1021/jm00102a017

文献信息

• 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个碳原子的低烷基，但当Z是N时，R是低烷基；R.sub.1和R.sub.2是氢、卤素、低烷基、低烷氧基、硝基、低烷氧羰基或三氟甲基；Het从指定的杂环基团中选择，对抗病毒剂，特别是对抗小RNA病毒，包括多种鼻病毒菌株。
• 1,3,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral
  申请人：Sterling Drug Inc.

  公开号：US05110821A1

  公开（公告）日：1992-05-05

  Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms; R' is lower-alkyl or hydroxy-lower-alkyl or 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.

  分子式为##STR1##的化合物，其中：Y是3-9个碳原子的烷基桥；R'是低级烷基或羟基-低级烷基或1-5个碳原子；R.sub.1和R.sub.2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；R.sub.8是氢或1-5个碳原子的低级烷基，但当R.sub.8是氢时，R'为羟基-低级烷基，可用作抗病毒剂，特别是对抗小肠病毒，包括大量的鼻病毒菌株。
• 1,3,4-Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral
  申请人：Sterling Drug Inc.

  公开号：US04945164A1

  公开（公告）日：1990-07-31

  Compounds of the formula ##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 Het is selected from 1,3,4-oxadiazol-2-yl and 5-alkylated derivatives thereof, are useful as antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  式为##STR1##的化合物，其中：Y是3-9个碳原子的烷基桥；R'是1-5个碳原子的低烷基或羟基低烷基；R.sub.1和R.sub.2是氢、卤素、低烷基、低烷氧基、硝基、低烷氧羰基或三氟甲基；而Het是选自1,3,4-噁二唑-2-基和其5-烷基衍生物，可用作抗病毒剂，特别是对抗许多种鼻病毒的畸变病毒。
• Thiazolylphenoxyalkylisoxazoles, related compounds, and their use as
  申请人：Sterling Drug Inc.

  公开号：US05051437A1

  公开（公告）日：1991-09-24

  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 thiazole, benzothiazole and benzoxazole groups, are useful as antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  式为##STR1##的化合物，其中：Y是3-9个碳原子的烷基桥；Z为N或HC；R为氢或1-5个碳原子的低烷基，但当Z为N时，R为低烷基；R.sub.1和R.sub.2为氢、卤素、低烷基、低烷氧基、硝基、低烷氧羰基或三氟甲基；Het选自噻唑、苯并噻唑和苯并噁唑基团，可用作抗病毒剂，特别是对抗多种鼻病毒菌株的畏克病毒。
• Heterocyclic substituted-phenoxyalkyl-isoxazoles and-furans, their preparation and use as antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0207453A2

  公开（公告）日：1987-01-07

  Compounds of the formula are disclosed, wherein: Y is an alkylene bridge of 3-9 carbon atoms; Z is N or HC; R is hydrogen or lower-alkyl of 1-3 carbon atoms, with the proviso that when Z is N, R is lower-alkyl; R1 and R2 are each hydrogen, halogen, methyl, nitro, lower-alkoxycarbonyl or trifluoromethyl; and Het is a heterocyclic group, and pharmaceutically acceptable acid addition salts thereof, as well as methods for preparation and use thereof. The compounds exhibit valuable antiviral properties.

  公开了式 公开了式 Y 是 3-9 个碳原子的亚烷基桥； Z 是 N 或 HC R 是氢或 1-3 个碳原子的低级烷基，但当 Z 是 N 时，R 是低级烷基； R1 和 R2 分别是氢、卤素、甲基、硝基、低级烷氧基羰基或三氟甲基；以及 Het 是杂环基团，及其药学上可接受的酸加成盐，以及其制备和使用方法。这些化合物具有宝贵的抗病毒特性。