(2R)-2-[[1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-ylidene]amino]-3-sulfanylpropanoic acid | 1241990-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: (2R)-2-[[1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-ylidene]amino]-3-sulfanylpropanoic acid
• CAS: 1241990-37-3
• 化学式: C₂₄H₂₇NO₁₀S
• 分子量: 521.545
• InChiKey: DELRFTALDGFLSO-ODDPEDEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  202
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R)-2-[[1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-ylidene]amino]-3-sulfanylpropanoic acid 在 Jones reagent 作用下， 以 甲醇 为溶剂， 以62%的产率得到(2R)-2-[[1,8-dihydroxy-3-(hydroxymethyl)-10H-anthracen-9-ylidene]amino]-3-sulfanylpropanoic acid
  参考文献：
  名称：

  Synthesis of cytotoxic and antioxidant Schiff's base analogs of aloin

  摘要：

  Aloin (10-glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthracenone), a bioactive compound in Aloe vera, although known to have an anticancer effect, has not been used in current drug research. Optimization of the lead structure could enhance the utility of this compound. Hence, aloin was modified using natural amino acids to produce Schiff's base, a potential pharmacophore, and its corresponding aglycones. The synthetic derivatives exhibited significant enhancement in their efficacy toward antioxidant (DPPH radical scavenging) and cytotoxic activities than those of the parent compound, aloin showing promise for application in cancer treatment.

  DOI：

  10.1080/10286021003775327
• 作为产物：
  描述：

  aloin 、 L-半胱氨酸 在 硫酸 作用下， 以 甲醇 为溶剂， 以57%的产率得到(2R)-2-[[1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-ylidene]amino]-3-sulfanylpropanoic acid
  参考文献：
  名称：

  Synthesis of cytotoxic and antioxidant Schiff's base analogs of aloin

  摘要：

  Aloin (10-glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthracenone), a bioactive compound in Aloe vera, although known to have an anticancer effect, has not been used in current drug research. Optimization of the lead structure could enhance the utility of this compound. Hence, aloin was modified using natural amino acids to produce Schiff's base, a potential pharmacophore, and its corresponding aglycones. The synthetic derivatives exhibited significant enhancement in their efficacy toward antioxidant (DPPH radical scavenging) and cytotoxic activities than those of the parent compound, aloin showing promise for application in cancer treatment.

  DOI：

  10.1080/10286021003775327