(R)-methyl 2-(1-hydroxy-6-thioxo-1,6-dihydropyridine-2-carboxamido)propanoate | 1609646-57-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-methyl 2-(1-hydroxy-6-thioxo-1,6-dihydropyridine-2-carboxamido)propanoate
• CAS: 1609646-57-2
• 化学式: C₁₀H₁₂N₂O₄S
• 分子量: 256.282
• InChiKey: WSHKWCHVGDVFOZ-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.56
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-(1-hydroxy-6-thioxo-1,6-dihydropyridine-2-carboxamido)propanoate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 以64%的产率得到(R)-2-(1-hydroxy-6-thioxo-1,6-dihydropyridine-2-carboxamido)propanoic acid
  参考文献：
  名称：

  Cell permeable vanX inhibitors as vancomycin re-sensitizing agents

  摘要：

  VanX is an induced zinc metallo D-Ala-D-Ala dipeptidase involved in the viable remodeling of bacterial cell wall that is essential for the development of VREF. Here we report two cyclic thiohydroxamic acid-based peptide analogs that were designed, synthesized and investigated as vancomycin re-sensitizing agents. These compounds exhibit low micromolar inhibitory activity against vanX, with low cytotoxicity and were shown to increase vancomycin sensitivity against VREF. The improved pharmacological properties of these novel inhibitors over previous transition state mimics should provide an enhanced platform for designing potent vanX inhibitors for overcoming vancomycin resistance. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.097
• 作为产物：
  描述：

  2-Bromo-6-carboxy-1-hydroxypyridin-1-ium 在 sodium hydrogen sulfide 、 sodiumsulfide nonahydrate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 36.17h， 生成 (R)-methyl 2-(1-hydroxy-6-thioxo-1,6-dihydropyridine-2-carboxamido)propanoate
  参考文献：
  名称：

  Cell permeable vanX inhibitors as vancomycin re-sensitizing agents

  摘要：

  VanX is an induced zinc metallo D-Ala-D-Ala dipeptidase involved in the viable remodeling of bacterial cell wall that is essential for the development of VREF. Here we report two cyclic thiohydroxamic acid-based peptide analogs that were designed, synthesized and investigated as vancomycin re-sensitizing agents. These compounds exhibit low micromolar inhibitory activity against vanX, with low cytotoxicity and were shown to increase vancomycin sensitivity against VREF. The improved pharmacological properties of these novel inhibitors over previous transition state mimics should provide an enhanced platform for designing potent vanX inhibitors for overcoming vancomycin resistance. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.097