5-<3,5-dichloro-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>phenyl>-1H-tetrazole | 107311-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-<3,5-dichloro-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>phenyl>-1H-tetrazole
• 英文别名: 5-[5-[2,6-dichloro-4-(2H-tetrazol-5-yl)phenoxy]pentyl]-3-methyl-1,2-oxazole
• CAS: 107311-85-3
• 化学式: C₁₆H₁₇Cl₂N₅O₂
• 分子量: 382.249
• InChiKey: SZWKYJRAUZBBGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-<3,5-dichloro-4-<<5-(3-methyl-5-isoxazolyl)pentyl>oxy>phenyl>-1H-tetrazole 、 碘甲烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以14%的产率得到5-{3,5-Dichloro-4-[5-(3-methyl-isoxazol-5-yl)-pentyloxy]-phenyl}-1-methyl-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：

  5-(5-溴戊基)-3-甲基异恶唑 在 sodium azide 、 potassium carbonate 、 氯化铵 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 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

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。
• 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。
• US4857539A
  申请人：——

  公开号：US4857539A

  公开（公告）日：1989-08-15
• Antirhinoviral activity of heterocyclic analogs of Win 54954
  作者：Thomas R. Bailey、Guy D. Diana、Paul J. Kowalczyk、Vahan Akullian、Michael A. Eissenstat、David Cutcliffe、John P. Mallamo、Philip M. Carabateas、Daniel C. Pevear

  DOI：10.1021/jm00102a017

  日期：1992.11

  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.