S-[2-[4,5-Dihydro-3-(4-methoxyphenyl)-5-isoxazolyl]-2-oxoethyl] ethanethioate | 473253-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: S-[2-[4,5-Dihydro-3-(4-methoxyphenyl)-5-isoxazolyl]-2-oxoethyl] ethanethioate
• 英文别名: S-[2-[3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]-2-oxoethyl] ethanethioate
• CAS: 473253-41-7
• 化学式: C₁₄H₁₅NO₄S
• 分子量: 293.343
• InChiKey: BADBVFOYRXPLRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-[2-[4,5-Dihydro-3-(4-methoxyphenyl)-5-isoxazolyl]-2-oxoethyl] ethanethioate 在 肼 作用下， 以 四氢呋喃 为溶剂， 生成 2-Mercapto-1-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]ethanone 、 2,5-Bis[3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]-1,4-dithiane-2,5-diol
  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：

  N-hydroxy-4-methoxybenzenecarboximidoyl chloride 在 N-甲基吗啉 、 sodium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 S-[2-[4,5-Dihydro-3-(4-methoxyphenyl)-5-isoxazolyl]-2-oxoethyl] ethanethioate
  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

文献信息

• Inhibition of the Antibacterial Target UDP-(3-<i>O</i>-acyl)-<i>N</i>-acetylglucosamine Deacetylase (LpxC):  Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups
  作者：Michael C. Pirrung、L. Nathan Tumey、Christian R. H. Raetz、Jane E. Jackman、Karnem Snehalatha、Amanda L. McClerren、Carol A. Fierke、Stephanie L. Gantt、Kristin M. Rusche

  DOI：10.1021/jm020183v

  日期：2002.9.1

  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.