7-deacetylcandidaspongiolide A | 1311277-58-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 7-deacetylcandidaspongiolide A
• 英文别名: precandidaspongiolide A；(3R,4S,5S,7R,8R,9E,11S,14S,15S,17R)-3,8,14,15-tetrahydroxy-15-(hydroxymethyl)-17-[(S)-hydroxy-[(2R,3R)-2-methyl-3-[(Z,2S)-pent-3-en-2-yl]oxiran-2-yl]methyl]-4-methoxy-5,7,9,11-tetramethyl-1-oxacyclooctadec-9-ene-2,6,12,16-tetrone
• CAS: 1311277-58-3
• 化学式: C₃₂H₅₀O₁₃
• 分子量: 642.741
• InChiKey: GSZIKTHZIXMUOP-NSRLGBFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  221
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  7-deacetylcandidaspongiolide A 、 乙酰氯 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以41%的产率得到28-acetylprecandidaspongiolide A
  参考文献：
  名称：

  New Candidaspongiolides, Tedanolide Analogues That Selectively Inhibit Melanoma Cell Growth

  摘要：

  Extracts of the sponge genus Candidaspongia showed selective cytotoxicity toward melanoma cells in the NCI 60-cell-line screen. Continued investigation of the Candidaspongia sp. extracts led to the isolation of three new tedanolide analogues, precandidaspongiolides A (1) and B (2) and candidaspongiolide B (4), as well as candidaspongiolide A (3) and tedanolide (5). Semisynthetic derivatives were also generated to develop SAR. Candidaspongiolides A/B were the most potent and showed low nanomolar activity against several melanoma cell lines.

  DOI：

  10.1021/ol201329p