Purpuromycin | 53969-01-0

• 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: Purpuromycin
• 英文别名: Hydroxyrubromycin；methyl 4,4',9',10-tetrahydroxy-7'-methoxy-5',8',9-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
• CAS: 53969-01-0
• 化学式: C₂₆H₁₈O₁₃
• 分子量: 538.421
• InChiKey: VGXVKHPGBHVPMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Purpuromycin 在 吡啶 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 pyridinium hydrobromide perbromide 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 4',9',10-triacetyl-6'-bromopurpuromycin
  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-4-O-(tetrahydro-2H-pyran-2-yl)-purpuromycin 在 吡啶 、 对甲苯磺酸 、 二乙胺 、 苄胺 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 Purpuromycin
  参考文献：
  名称：

  Trani; Dallanoce; Ferrari, Il Farmaco, 1996, vol. 51, # 7, p. 503 - 512

  摘要：

  DOI：

文献信息

• Trani; Kettenring; Ripamonti, Il Farmaco, 1993, vol. 48, # 5, p. 637 - 651
  作者：Trani、Kettenring、Ripamonti、Goldstein、Ciabatti

  DOI：——

  日期：——
• Semisynthetic Derivatives of Purpuromycin as Potential Topical Agents for Vaginal Infections
  作者：Aldo Trani、Clelia Dallanoce、Gianbattista Panzone、Franca Ripamonti、Beth P. Goldstein、Romeo Ciabatti

  DOI：10.1021/jm960672t

  日期：1997.3.1

  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.
• Trani; Dallanoce; Ferrari, Il Farmaco, 1996, vol. 51, # 7, p. 503 - 512
  作者：Trani、Dallanoce、Ferrari、Goldstein、Ripamonti、Ciabatti

  DOI：——

  日期：——