(R)-2-(1-hydroxy-6-thioxo-1,6-dihydropyridine-2-carboxamido)-2-phenylacetic acid | 1609646-55-0

• 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)-2-(1-hydroxy-6-thioxo-1,6-dihydropyridine-2-carboxamido)-2-phenylacetic acid
• 英文别名: (2R)-2-[(1-hydroxy-6-sulfanylidenepyridine-2-carbonyl)amino]-2-phenylacetic acid
• CAS: 1609646-55-0
• 化学式: C₁₄H₁₂N₂O₄S
• 分子量: 304.326
• InChiKey: MUTGTTZIVAJIJK-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-溴-2-吡啶羧酸 在 sodium hydrogen sulfide 、 sodiumsulfide nonahydrate 、 lithium hydroxide monohydrate 、 双氧水 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 三氟乙酸 为溶剂， 反应 49.17h， 生成 (R)-2-(1-hydroxy-6-thioxo-1,6-dihydropyridine-2-carboxamido)-2-phenylacetic 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