5-{5-[2,6-Dichloro-4-(thien-2-yl)phenoxy]pentyl}-3-methylisoxazole

• 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: 5-{5-[2,6-Dichloro-4-(thien-2-yl)phenoxy]pentyl}-3-methylisoxazole
• 英文别名: 5-{5-[2,6-Dichloro-4-(2-thienyl)phenoxy]pentyl}-3-methylisoxazole；5-[5-[2,6-Dichloro-4-(2-thienyl)phenoxy]pentyl]-3-methyl-isoxazole；5-[5-(2,6-dichloro-4-thiophen-2-ylphenoxy)pentyl]-3-methyl-1,2-oxazole
• 化学式: C₁₉H₁₉Cl₂NO₂S
• 分子量: 396.337
• InChiKey: UQQHLLKYIARHTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(5-溴戊基)-3-甲基异恶唑 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.0h， 生成 5-{5-[2,6-Dichloro-4-(thien-2-yl)phenoxy]pentyl}-3-methylisoxazole
  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-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.