methyl-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]phosphinic acid 2-chloro-ethyl ester | 473253-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]phosphinic acid 2-chloro-ethyl ester
• 英文别名: 5-[2-Chloroethoxy(methyl)phosphoryl]-3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazole
• CAS: 473253-50-8
• 化学式: C₁₃H₁₇ClNO₄P
• 分子量: 317.709
• InChiKey: ZOOKNJYBWCPCRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]phosphinic acid 2-chloro-ethyl ester 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以41%的产率得到3-(4-Methoxyphenyl)-4,5-dihydroisoxazol-5-yl(methyl)phosphinic acid
  参考文献：
  名称：

  Inhibition of the Antibacterial Target UDP-(3-O-acyl)-N-acetylglucosamine Deacetylase (LpxC):  Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups

  摘要：

  UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase (LpxC) is a zinc amidase that catalyzes the second step of lipid A biosynthesis in Gram negative bacteria. Known inhibitors of this enzyme are oxazolines incorporating a hydroxamic acid at the 4-position, which is believed to coordinate to the single essential zinc ion. A new structural class of inhibitors was designed to incorporate a more stable and more synthetically. versatile isoxazoline core. The synthetic versatility of the isoxazoline allowed for a broad study of metal binding. groups. Nine of 17 isoxazolines, each incorporating a different potential metal binding functional group, were found to exhibit enzyme inhibitory activity, including one that is more active than the corresponding hydroxamic acid. Additionally, a designed affinity label inhibits LpxC in a time-dependent manner.

  DOI：

  10.1021/jm020183v
• 作为产物：
  描述：

  Methyl-2-chloraethyl-phosphinsaeure-2-chloraethylester 在 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 methyl-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]phosphinic acid 2-chloro-ethyl ester
  参考文献：
  名称：

  Inhibition of the Antibacterial Target UDP-(3-O-acyl)-N-acetylglucosamine Deacetylase (LpxC):  Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups

  摘要：

  UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase (LpxC) is a zinc amidase that catalyzes the second step of lipid A biosynthesis in Gram negative bacteria. Known inhibitors of this enzyme are oxazolines incorporating a hydroxamic acid at the 4-position, which is believed to coordinate to the single essential zinc ion. A new structural class of inhibitors was designed to incorporate a more stable and more synthetically. versatile isoxazoline core. The synthetic versatility of the isoxazoline allowed for a broad study of metal binding. groups. Nine of 17 isoxazolines, each incorporating a different potential metal binding functional group, were found to exhibit enzyme inhibitory activity, including one that is more active than the corresponding hydroxamic acid. Additionally, a designed affinity label inhibits LpxC in a time-dependent manner.

  DOI：

  10.1021/jm020183v