(S)-2-acetyl-6-(2-aminothiazol-4-yl)-3,7,9-trihydroxy-8,9bdimethyldibenzo[b,d]furan-1(9b-H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (S)-2-acetyl-6-(2-aminothiazol-4-yl)-3,7,9-trihydroxy-8,9bdimethyldibenzo[b,d]furan-1(9b-H)-one
• 英文别名: (s)-2-Acetyl-6-(2-aminothiazol-4-yl)-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bh)-one；(9bS)-2-acetyl-6-(2-amino-1,3-thiazol-4-yl)-3,7,9-trihydroxy-8,9b-dimethyldibenzofuran-1-one
• 化学式: C₁₉H₁₆N₂O₆S
• 分子量: 400.412
• InChiKey: JMQCZWYLLWEATR-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  171
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (+)-usnic acid 在 氢溴酸 、 溴 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.0h， 生成 (S)-2-acetyl-6-(2-aminothiazol-4-yl)-3,7,9-trihydroxy-8,9bdimethyldibenzo[b,d]furan-1(9b-H)-one
  参考文献：
  名称：

  Synthesis and activity of (+)-usnic acid and (−)-usnic acid derivatives containing 1,3-thiazole cycle against Mycobacterium tuberculosis

  摘要：

  New usnic acid (UA) derivatives were investigated in vitro to elucidate their potential inhibitory activities on the growth of Mycobacterium smegmatis and Mycobacterium tuberculosis. Seven pairs of enantiomers of thiazole UA derivatives were tested using the M. smegmatis strain mc(2) 155 test system, and the "structure-activity" relationship was established. The most active compounds were (+)-3 and (-)-3, and their kinase inhibitory activities were investigated. The results obtained using the Streptomyces lividans APHVIII+ and M. smegmatis APHVIII+ test systems indicated the significant protein kinase activity of these compounds and revealed the species specificity of the actions of the dextro- and levorotatory isomers. Both isomers, (+)-3 and (-)-3, possess similar inhibitory activity against M. tuberculosis H37Rv. The action of the isomers on eukaryotic cells was also investigated, and the results demonstrate that the dextrorotatory isomer (+)-3 leads to the lysis of intact macrophages to a degree higher than that obtained spontaneously and significantly higher than that obtained with the levorotatory isomer.

  DOI：

  10.1007/s00044-015-1348-2

文献信息

• Synthesis and activity of (+)-usnic acid and (−)-usnic acid derivatives containing 1,3-thiazole cycle against Mycobacterium tuberculosis
  作者：Olga B. Bekker、Dmitry N. Sokolov、Olga A. Luzina、Nina I. Komarova、Yuriy V. Gatilov、Sofia N. Andreevskaya、Tatiana G. Smirnova、Dmitry A. Maslov、Larisa N. Chernousova、Nariman F. Salakhutdinov、Valery. N. Danilenko

  DOI：10.1007/s00044-015-1348-2

  日期：2015.7

  New usnic acid (UA) derivatives were investigated in vitro to elucidate their potential inhibitory activities on the growth of Mycobacterium smegmatis and Mycobacterium tuberculosis. Seven pairs of enantiomers of thiazole UA derivatives were tested using the M. smegmatis strain mc(2) 155 test system, and the "structure-activity" relationship was established. The most active compounds were (+)-3 and (-)-3, and their kinase inhibitory activities were investigated. The results obtained using the Streptomyces lividans APHVIII+ and M. smegmatis APHVIII+ test systems indicated the significant protein kinase activity of these compounds and revealed the species specificity of the actions of the dextro- and levorotatory isomers. Both isomers, (+)-3 and (-)-3, possess similar inhibitory activity against M. tuberculosis H37Rv. The action of the isomers on eukaryotic cells was also investigated, and the results demonstrate that the dextrorotatory isomer (+)-3 leads to the lysis of intact macrophages to a degree higher than that obtained spontaneously and significantly higher than that obtained with the levorotatory isomer.