5-{5-[2,6-dimethyl-4-(2-methoxycarbonylmethyl-2H-tetrazol-5-yl)phenoxy]pentyl}-3-methylisoxazole | 126225-53-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-{5-[2,6-dimethyl-4-(2-methoxycarbonylmethyl-2H-tetrazol-5-yl)phenoxy]pentyl}-3-methylisoxazole
• 英文别名: Methyl 2-[5-[3,5-dimethyl-4-[5-(3-methylisoxazol-5-yl)pentoxy]phenyl]tetrazol-2-yl]acetate；methyl 2-[5-[3,5-dimethyl-4-[5-(3-methyl-1,2-oxazol-5-yl)pentoxy]phenyl]tetrazol-2-yl]acetate
• CAS: 126225-53-4
• 化学式: C₂₁H₂₇N₅O₄
• 分子量: 413.476
• InChiKey: ATBOORQKAHSQGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-{5-[2,6-dimethyl-4-(2-methoxycarbonylmethyl-2H-tetrazol-5-yl)phenoxy]pentyl}-3-methylisoxazole 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以6.56 g (88%)的产率得到5-{5-[2,6-dimethyl-4-[2-(2-hydroxyethyl)-2H-tetrazol-5-yl]phenoxy]pentyl}-3-methylisoxazole
  参考文献：
  名称：

  Heterocyclic substituted-phenoxyalkylisoxazoles as antiviral useful

  摘要：

  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。

  公开号：

  US04857539A1
• 作为产物：
  描述：

  5-(5-溴戊基)-3-甲基异恶唑 在 sodium azide 、 盐酸羟胺 、 乙酸酐 、 potassium carbonate 、 氯化铵 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 91.0h， 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

文献信息

• US4857539A
  申请人：——

  公开号：US4857539A

  公开（公告）日：1989-08-15
• 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。
• 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.