5-(4-methoxy-3,5-dimethylphenyl)-2H-tetrazole | 152775-46-7

• 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-(4-methoxy-3,5-dimethylphenyl)-2H-tetrazole
• CAS: 152775-46-7
• 化学式: C₁₀H₁₂N₄O
• 分子量: 204.231
• InChiKey: KXPGKRJHUBZWOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-methoxy-3,5-dimethylphenyl)-2H-tetrazole 在 lithium aluminium tetrahydride 、 溴 、 三溴化硼 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 31.67h， 生成 5-<4-<<3-<3-(bromomethyl)-5-isoxazolyl>propyl>oxy>-3,5-dimethylphenyl>-2-methyl-2-H-tetrazole
  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
• 作为产物：
  描述：

  3,5-二甲基-4-甲氧基苯甲腈 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-(4-methoxy-3,5-dimethylphenyl)-2H-tetrazole
  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

• 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.