Trifluoro-acetic acid 2,6-dibromo-4-(5-oxo-2-trifluoromethyl-4,5-dihydro-oxazol-4-ylmethyl)-phenyl ester | 740808-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Trifluoro-acetic acid 2,6-dibromo-4-(5-oxo-2-trifluoromethyl-4,5-dihydro-oxazol-4-ylmethyl)-phenyl ester
• CAS: 740808-93-9
• 化学式: C₁₃H₅Br₂F₆NO₄
• 分子量: 512.985
• InChiKey: AKNJBVDWGFQGJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-acetic acid 2,6-dibromo-4-(5-oxo-2-trifluoromethyl-4,5-dihydro-oxazol-4-ylmethyl)-phenyl ester 在 三氟乙酸 作用下， 生成 (3,5-dibromo-4-hydroxy-phenyl)-pyruvic acid
  参考文献：
  名称：

  Synthesis of a bromotyrosine-derived natural product inhibitor of mycothiol- S -conjugate amidase

  摘要：

  Recently we described the structures of two new bromotyrosine-derived alkaloids that inhibit the detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis. Here we describe a concise total synthesis of bromotyrosine oxime 1. The six-step synthesis of 1 utilized a trifluoromethyloxazole intermediate, whose hydrolysis product underwent alkylation and coupling to agmatine to give the inhibitor in similar to40% overall yield. Oxime 1 inhibited MCA and its homolog AcGI deacetylase with IC50 values of 30 and 150 muM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.095
• 作为产物：
  描述：

  3,5-二溴-DL-酪氨酸 、 三氟乙酸酐 反应 18.0h， 生成 Trifluoro-acetic acid 2,6-dibromo-4-(5-oxo-2-trifluoromethyl-4,5-dihydro-oxazol-4-ylmethyl)-phenyl ester
  参考文献：
  名称：

  Synthesis of a bromotyrosine-derived natural product inhibitor of mycothiol- S -conjugate amidase

  摘要：

  Recently we described the structures of two new bromotyrosine-derived alkaloids that inhibit the detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis. Here we describe a concise total synthesis of bromotyrosine oxime 1. The six-step synthesis of 1 utilized a trifluoromethyloxazole intermediate, whose hydrolysis product underwent alkylation and coupling to agmatine to give the inhibitor in similar to40% overall yield. Oxime 1 inhibited MCA and its homolog AcGI deacetylase with IC50 values of 30 and 150 muM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.095