[5-(5-氯戊基)-1,2-恶唑-3-基]甲醇 | 107355-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: [5-(5-氯戊基)-1,2-恶唑-3-基]甲醇
• 英文名称: 5-(5-chloropentyl)-3-(hydroxymethyl)isoxazole
• 英文别名: 5-(5-chloropentyl)-3-hydroxymethylisoxazole；[5-(5-Chloropentyl)-1,2-oxazol-3-YL]methanol
• CAS: 107355-86-2
• 化学式: C₉H₁₄ClNO₂
• 分子量: 203.669
• InChiKey: LQOPDGLFUCSCRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [5-(5-氯戊基)-1,2-恶唑-3-基]甲醇 在 sodium azide 、 potassium carbonate 、 氯化铵 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 168.0h， 生成 Benzoic acid 2-(5-{5-[2,6-dimethyl-4-(2-methyl-2H-tetrazol-5-yl)-phenoxy]-pentyl}-isoxazol-3-ylmethoxymethoxy)-ethyl ester
  参考文献：
  名称：

  CoMFA分析人鼻病毒14结合袋中抗小核糖核酸病毒化合物的相互作用。

  摘要：

  CoMFA分析对八种与二恶草腈有关的化合物进行了分析，这些化合物的X射线结构已与HRV-14结合，已确定其活性与化合物的空间效应有很强的正相关性，特别是在化合物结合位点的孔端与静电效应相关。这些结果证实了先前发现的事实，即这些化合物的活性高度依赖于log p表示的疏水性。CoMFA研究还证实了使用体积图比较一系列活性和非活性化合物的结果，结果表明分子孔末端的体积有助于高水平的抗病毒活性，而环周围的体积过大则导致活性降低。

  DOI：

  10.1021/jm00084a005
• 作为产物：
  描述：

  3-羟甲基-5-甲基异恶唑 、 1-溴-4-氯丁烷 在 正丁基锂 作用下， 生成 [5-(5-氯戊基)-1,2-恶唑-3-基]甲醇
  参考文献：
  名称：

  1,3,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral

  摘要：

  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。

  公开号：

  US05110821A1
• 作为试剂：
  描述：

  5-(5-溴戊基)-3-甲基异恶唑 以 [5-(5-氯戊基)-1,2-恶唑-3-基]甲醇 为溶剂， 生成 5-{5-[2,6-dichloro-4-(1,3,4-oxadiazol-2-yl)phenoxy]pentyl}-3-hydroxymethylisoxazole
  参考文献：
  名称：

  1,3,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral

  摘要：

  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。

  公开号：

  US05110821A1

文献信息

• Isoxazole and furan derivatives, their preparation and use as antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0207454A2

  公开（公告）日：1987-01-07

  Compounds of the formula are wherein: R is hydrogen or alkyl of 1 to 3 carbon atoms optionally substituted by hydroxy, lower-alkoxy, lower-alkoxyalkoxy, lower-acyloxy, halo or N=Z', wherein N=Z' is amino, lower- slkanoylamino, lower-alkylamino, di-lower-alkylamino, 1-pyrrolidyl, 1-piperidiny) or 4-morpholinyl; X is 0 or CH2; Y is an alkylene bridge of 3-9 carbon atoms, optionally interrupted by an olefinic linkage; Z is N or R5C, where R5 is hydrogen or lower-alkanoyl, with the proviso that when Z is N, R is other than hydrogen; m is 0 or 1; R, and R2 are each halogen, methyl, nitro, lower- alkoxycarbonyl or trifluoromethyl; and R3 and R4 are each hydrogen or lower-alkyl of 1-3 carbon atoms; and pharmaceutically acceptable acid-addition salts thereof, as well as methods for preparation and use thereof. The compound exhibit valuable antiviral properties.

  式中的化合物 其中 R 是氢或任选被羟基、低级烷氧基、低级烷氧基烷氧基、低级乙氧基、卤素或 N=Z' 取代的 1 至 3 个碳原子的烷基，其中 N=Z' 是氨基、低级烷酰氨基、低级烷基氨基、二低级烷基氨基、1-吡咯烷基、1-哌啶基或 4-吗啉基； X 是 0 或 CH2； Y 是 3-9 个碳原子的亚烷基桥，可选择被烯烃链节打断； Z 是 N 或 R5C，其中 R5 是氢或低级烷酰基，但当 Z 是 N 时，R 不是氢； m 为 0 或 1； R 和 R2 分别是卤素、甲基、硝基、低级烷氧羰基或三氟甲基；以及 R3 和 R4 分别是氢或 1-3 个碳原子的低级烷基；以及 其药学上可接受的酸加成盐及其制备和使用方法。这些化合物具有宝贵的抗病毒特性。
• 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。
• A model for compounds active against human rhinovirus-14 based on x-ray crystallography data
  作者：Guy D. Diana、Adi M. Treasurywala、Thomas R. Bailey、Richard C. Oglesby、Daniel C. Pevear、Frank J. Dutko

  DOI：10.1021/jm00167a006

  日期：1990.5

  A number of (oxazolinylphenyl)isoxazoles have been synthesized and tested against human rhinovirus-14 (HRV-14). Several of the more active compounds have been examined by X-ray crystallography and their orientation in the compound binding site on the capsid protein of HRV-14 has been determined. Based on the minimum inhibitory concentration against HRV-14 and the X-ray conformation of the compounds, a model has been developed which distinguishes between the space-filling properties of the active and inactive compounds in this series. The model was generated by overlaying composite structures and comparing the van der Waals generated volume maps. The results of this study indicate that inactive compounds display areas of excessive bulk particularly around the phenyl ring, while the active compounds occupy space below the pore area of the compound binding site.
• Antipicornavirus activity of tetrazole analogs related to disoxaril
  作者：Guy D. Diana、David Cutcliffe、Deborah L. Volkots、John P. Mallamo、Thomas R. Bailey、Niranjan Vescio、Richard C. Oglesby、Theodore J. Nitz、Joseph Wetzel

  DOI：10.1021/jm00074a004

  日期：1993.10

  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.
• US4843087A
  申请人：——

  公开号：US4843087A

  公开（公告）日：1989-06-27