[3-Methyl-5-[4-(2-methyltetrazol-5-yl)phenoxy]pentyl] 4-methylbenzenesulfonate | 1027529-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [3-Methyl-5-[4-(2-methyltetrazol-5-yl)phenoxy]pentyl] 4-methylbenzenesulfonate
• CAS: 1027529-98-1
• 化学式: C₂₁H₂₆N₄O₄S
• 分子量: 430.528
• InChiKey: TXANMLQBPKEEQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [3-Methyl-5-[4-(2-methyltetrazol-5-yl)phenoxy]pentyl] 4-methylbenzenesulfonate 、 1-吡啶-4-咪唑啉-2-酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到1-{3-methyl-5-[4-(2-methyl-2H-tetrazol-5-yl)phenoxy]pentyl}-3-pyridin-4-ylimidazolidin-2-one
  参考文献：
  名称：

  Design, Synthesis, and Antipicornavirus Activity of 1-[5-(4-Arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one Derivatives

  摘要：

  A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.

  DOI：

  10.1021/jm050033v
• 作为产物：
  描述：

  戊烯二酸二甲酯 在 吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 26.0h， 生成 [3-Methyl-5-[4-(2-methyltetrazol-5-yl)phenoxy]pentyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  Design, Synthesis, and Antipicornavirus Activity of 1-[5-(4-Arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one Derivatives

  摘要：

  A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.

  DOI：

  10.1021/jm050033v

文献信息

• Design, Synthesis, and Antipicornavirus Activity of 1-[5-(4-Arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one Derivatives
  作者：Chih-Shiang Chang、Ying-Ting Lin、Shin-Ru Shih、Chung-Chi Lee、Yen-Chun Lee、Chia-Liang Tai、Sung-Nien Tseng、Jyh-Haur Chern

  DOI：10.1021/jm050033v

  日期：2005.5.1

  A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.