methyl 6'-bromo-4,4',9',10-tetrahydroxy-5',8',9-trioxo-7'-(2,2,2-trifluoroethylamino)spiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate | 151158-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 6'-bromo-4,4',9',10-tetrahydroxy-5',8',9-trioxo-7'-(2,2,2-trifluoroethylamino)spiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
• CAS: 151158-28-0
• 化学式: C₂₇H₁₇BrF₃NO₁₂
• 分子量: 684.331
• InChiKey: GSWQGNREGYZOPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  198
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 6'-bromo-4,4',9',10-tetrahydroxy-5',8',9-trioxo-7'-(2,2,2-trifluoroethylamino)spiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 以20%的产率得到methyl 4,4',9',10-tetrahydroxy-5',8',9-trioxo-7'-(2,2,2-trifluoroethylamino)spiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
  参考文献：
  名称：

  Semisynthetic Derivatives of Purpuromycin as Potential Topical Agents for Vaginal Infections

  摘要：

  Purpuromycin (1) is an antibiotic with a broad spectrum of antimicrobial activity, encompassing bacteria, fungi, and protozoa, particularly those involved in vaginal infections. With the aim of enhancing the solubility and reducing the serum binding, a chemical program of modifications was undertaken on the natural compound, and a new interesting series of derivatives at the naphthoquinone system was synthesized and evaluated as potential topical agents for vaginal infections. In particular three semisynthetic derivatives, 7'-amino (8a), 7'-methylamino (8b), 7'-ethylamino (8c), of 7'-demethoxypurpuromycin seemed to be the most promising. They were tested for in vitro activity against three of the most important vaginal pathogens and showed activity similar to that of purpuromycin against Candida isolates while they were significantly more active against Trichomonas vaginalis and Gardnerella vaginalis, which are cultured in media containing blood or serum. This is probably due to the fact that the activity of the derivatives is less antagonized by these supplements than that of purpuromycin.

  DOI：

  10.1021/jm960672t
• 作为产物：
  描述：

  4',9',10-triacetyl-6'-bromo-4-O-(tetrahydro-2H-pyran-2-yl)purpuromycin 在 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 生成 methyl 6'-bromo-4,4',9',10-tetrahydroxy-5',8',9-trioxo-7'-(2,2,2-trifluoroethylamino)spiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
  参考文献：
  名称：

  Semisynthetic Derivatives of Purpuromycin as Potential Topical Agents for Vaginal Infections

  摘要：

  Purpuromycin (1) is an antibiotic with a broad spectrum of antimicrobial activity, encompassing bacteria, fungi, and protozoa, particularly those involved in vaginal infections. With the aim of enhancing the solubility and reducing the serum binding, a chemical program of modifications was undertaken on the natural compound, and a new interesting series of derivatives at the naphthoquinone system was synthesized and evaluated as potential topical agents for vaginal infections. In particular three semisynthetic derivatives, 7'-amino (8a), 7'-methylamino (8b), 7'-ethylamino (8c), of 7'-demethoxypurpuromycin seemed to be the most promising. They were tested for in vitro activity against three of the most important vaginal pathogens and showed activity similar to that of purpuromycin against Candida isolates while they were significantly more active against Trichomonas vaginalis and Gardnerella vaginalis, which are cultured in media containing blood or serum. This is probably due to the fact that the activity of the derivatives is less antagonized by these supplements than that of purpuromycin.

  DOI：

  10.1021/jm960672t