3-acetyl-3,5,12-trihydroxy-1-[5-hydroxy-4-(4-hydroxyphenylaminocarbonylamino)-6-methylperhydro-2-pyranoloxy]-10-methoxy-(1S,3S)-1,2,3,4,6,11-hexahydro-6,11-naphthacenedione | 371754-31-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: 3-acetyl-3,5,12-trihydroxy-1-[5-hydroxy-4-(4-hydroxyphenylaminocarbonylamino)-6-methylperhydro-2-pyranoloxy]-10-methoxy-(1S,3S)-1,2,3,4,6,11-hexahydro-6,11-naphthacenedione
• CAS: 371754-31-3
• 化学式: C₃₆H₃₈N₂O₁₂
• 分子量: 690.704
• InChiKey: KJLDWEXPBUKNMD-WYPXXYHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  50.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  221.18
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  道诺霉素 、 4-hydroxyphenethylamino-4-nitrophenoxymethanone 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以46%的产率得到3-acetyl-3,5,12-trihydroxy-1-[5-hydroxy-4-(4-hydroxyphenylaminocarbonylamino)-6-methylperhydro-2-pyranoloxy]-10-methoxy-(1S,3S)-1,2,3,4,6,11-hexahydro-6,11-naphthacenedione
  参考文献：
  名称：

  Melanocyte-Directed enzyme prodrug therapy (MDEPT)

  摘要：

  Evaluation of second generation prodrugs for MDEPT, by oximetry, has highlighted structural properties that are advantageous and disadvantageous for efficient oxidation using mushroom tyrosinase. In particular, a sterically undemanding prodrug bis-(2-chloroethyl)amino-4-hydroxyphenylaminomethanone 28 was synthesised and found to be oxidised by mushroom tyrosinase at a superior rate to tyrosine methyl ester, the carboxylic acid of which is the natural substrate for tyrosinase. The more sterically demanding phenyl mustard prodrugs 9 and 10 were oxidised by mushroom tyrosinase at a similar rate to tyrosine methyl ester. In contrast, tyramine chain elongation via heteroatom insertion was detrimental and the rate of mushroom tyrosinase oxidation of phenyl mustard prodrugs 21 and 22 decreased by 10 nanomol/min. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00039-6