tert-butyl 2-(chloromethyl)benzoxazol-4-yl carbonate | 960286-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: tert-butyl 2-(chloromethyl)benzoxazol-4-yl carbonate
• 英文别名: Tert-butyl [2-(chloromethyl)-1,3-benzoxazol-4-yl] carbonate
• CAS: 960286-51-5
• 化学式: C₁₃H₁₄ClNO₄
• 分子量: 283.711
• InChiKey: VLPIYXHPWFFSAV-UHFFFAOYSA-N

物化性质

• 沸点：
  374.2±38.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(chloromethyl)benzoxazol-4-yl carbonate 、 2,4,6-三氟苯酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 Tert-butyl [2-[(2,4,6-trifluorophenoxy)methyl]-1,3-benzoxazol-4-yl] carbonate
  参考文献：
  名称：

  Design, synthesis and antifungal activity of isosteric analogues of benzoheterocyclic N-myristoyltransferase inhibitors

  摘要：

  N-myristoyltransferase (NMT) has been a promising new target for the design of novel antifungal agents with new mode of action. A series of benzoxazole and indole derivatives were designed and synthesized as isosteric analogues of benzoheterocyclic NMT Inhibitors. In vitro antifungal assay indicated that the benzoxazole derivatives were far more potent than the indoles. Molecular docking studies revealed that the hydrogen bonding interaction between the benzoheterocyclic core and NMT might be essential in the orientation of the inhibitor to a proper position. The antifungal activity of benzoxazole derivative 8f was comparable or superior to that of fluconazole, which can serve as a good starting point for further studies of structural diversity of the benzoheterocyclic NMT inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.007
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-(chloromethyl)-4-hydroxybenzoxazole 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以91.7%的产率得到tert-butyl 2-(chloromethyl)benzoxazol-4-yl carbonate
  参考文献：
  名称：

  Design, synthesis and antifungal activity of isosteric analogues of benzoheterocyclic N-myristoyltransferase inhibitors

  摘要：

  N-myristoyltransferase (NMT) has been a promising new target for the design of novel antifungal agents with new mode of action. A series of benzoxazole and indole derivatives were designed and synthesized as isosteric analogues of benzoheterocyclic NMT Inhibitors. In vitro antifungal assay indicated that the benzoxazole derivatives were far more potent than the indoles. Molecular docking studies revealed that the hydrogen bonding interaction between the benzoheterocyclic core and NMT might be essential in the orientation of the inhibitor to a proper position. The antifungal activity of benzoxazole derivative 8f was comparable or superior to that of fluconazole, which can serve as a good starting point for further studies of structural diversity of the benzoheterocyclic NMT inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.007

文献信息

• Design, synthesis and antifungal activity of isosteric analogues of benzoheterocyclic N-myristoyltransferase inhibitors
  作者：Chunquan Sheng、Hui Xu、Wenya Wang、Yongbing Cao、Guoqiang Dong、Shengzheng Wang、Xiaoying Che、Haitao Ji、Zhenyuan Miao、Jianzhong Yao

  DOI：10.1016/j.ejmech.2010.03.007

  日期：2010.9

  N-myristoyltransferase (NMT) has been a promising new target for the design of novel antifungal agents with new mode of action. A series of benzoxazole and indole derivatives were designed and synthesized as isosteric analogues of benzoheterocyclic NMT Inhibitors. In vitro antifungal assay indicated that the benzoxazole derivatives were far more potent than the indoles. Molecular docking studies revealed that the hydrogen bonding interaction between the benzoheterocyclic core and NMT might be essential in the orientation of the inhibitor to a proper position. The antifungal activity of benzoxazole derivative 8f was comparable or superior to that of fluconazole, which can serve as a good starting point for further studies of structural diversity of the benzoheterocyclic NMT inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.