4,6,3',4'-tetra-O-acetyl-9-O-(methylsulfonyl)aranciamycin | 141958-45-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 4,6,3',4'-tetra-O-acetyl-9-O-(methylsulfonyl)aranciamycin
• 英文别名: [(2S,3S,4R,5R,6S)-4-acetyloxy-6-[[(1R,2S,3S)-10,12-diacetyloxy-2-methoxy-3-methyl-3-methylsulfonyloxy-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy]-5-methoxy-2-methyloxan-3-yl] acetate
• CAS: 141958-45-4
• 化学式: C₃₆H₃₈O₁₈S
• 分子量: 790.753
• InChiKey: WAYMQLYXNVEMEY-BCKGJOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  245
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  4,6,3',4'-tetra-O-acetyl-9-O-(methylsulfonyl)aranciamycin 在 甲醇 、 potassium carbonate 作用下， 反应 96.0h， 以26%的产率得到9-Epiaranciamycin
  参考文献：
  名称：

  Inhibition of collagenase by aranciamycin and aranciamycin derivatives.

  摘要：

  Aranciamycin (1), an anthracycline antibiotic, was found to be an inhibitor of Clostridium histolyticum collagenase, with an IC50 = 3.7 x 10(-7) M. Elastase and trypsin were not inhibited at concentrations less-than-or-equal-to 10(-5) M. A number of aranciamycin derivatives 2-13 were prepared and tested for collagenase inhibition. While loss of activity was found for derivatives modified in the sugar ring or rings B and D of the aglycone, increased potency was found when the tertiary alcohol at C-9 was esterified. All compounds 1-13 were found to inhibit DNA synthesis of Yoshida sarcoma tumor cells.

  DOI：

  10.1021/jm00093a008
• 作为产物：
  描述：

  甲基磺酰氯 、 4,6,3',4'-tetra-O-acetylaranciamycin 在 吡啶 作用下， 反应 2.25h， 以73%的产率得到4,6,3',4'-tetra-O-acetyl-9-O-(methylsulfonyl)aranciamycin
  参考文献：
  名称：

  Inhibition of collagenase by aranciamycin and aranciamycin derivatives.

  摘要：

  Aranciamycin (1), an anthracycline antibiotic, was found to be an inhibitor of Clostridium histolyticum collagenase, with an IC50 = 3.7 x 10(-7) M. Elastase and trypsin were not inhibited at concentrations less-than-or-equal-to 10(-5) M. A number of aranciamycin derivatives 2-13 were prepared and tested for collagenase inhibition. While loss of activity was found for derivatives modified in the sugar ring or rings B and D of the aglycone, increased potency was found when the tertiary alcohol at C-9 was esterified. All compounds 1-13 were found to inhibit DNA synthesis of Yoshida sarcoma tumor cells.

  DOI：

  10.1021/jm00093a008