(25R)-26-dansylamido-3β-O-[4-O-(α-L-arabinofuranosyl)-2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]furost-5-ene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (25R)-26-dansylamido-3β-O-[4-O-(α-L-arabinofuranosyl)-2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]furost-5-ene
• 英文别名: N-[(2R)-4-[(1S,2S,4S,7S,8R,9S,12S,13R,16S)-16-[(2R,3R,4S,5S,6R)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-6-yl]-2-methylbutyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• 化学式: C₅₆H₈₄N₂O₁₇S
• 分子量: 1089.35
• InChiKey: VDCCTAXOHNSBIH-WGYRBPISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  76
• 可旋转键数：
  16
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  284
• 氢给体数：
  9
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  (25R)-26-amino-3β-O-[4-O-(α-L-arabinofuranosyl)-2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]furost-5-ene 、 丹酰氯 在 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以69%的产率得到(25R)-26-dansylamido-3β-O-[4-O-(α-L-arabinofuranosyl)-2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]furost-5-ene
  参考文献：
  名称：

  Fluorophore-Appended Steroidal Saponin (Dioscin and Polyphyllin D) Derivatives

  摘要：

  The synthesis of three fluorophore-appended derivatives of dioscin and polyphyllin D is reported herein. Starting from trillin, dansyl derivatives A-C were prepared in overall yields of 7-12% over 7-10 steps. A study of their behavior in a variety of polar solvents suggests that dansyl derivatives A-C are capable of micellar self-assembly and can maintain cytotoxicities (IC50 = 15-18 muM) against the HeLa carcinoma cell line evaluated by standard MTT assay.

  DOI：

  10.1021/ol0475616

文献信息

• Fluorophore-Appended Steroidal Saponin (Dioscin and Polyphyllin D) Derivatives
  作者：Zhiqi Yang、Ella Lai-Ming Wong、Tina Yuen-Ting Shum、Chi-Ming Che、Yongzheng Hui

  DOI：10.1021/ol0475616

  日期：2005.2.1

  The synthesis of three fluorophore-appended derivatives of dioscin and polyphyllin D is reported herein. Starting from trillin, dansyl derivatives A-C were prepared in overall yields of 7-12% over 7-10 steps. A study of their behavior in a variety of polar solvents suggests that dansyl derivatives A-C are capable of micellar self-assembly and can maintain cytotoxicities (IC50 = 15-18 muM) against the HeLa carcinoma cell line evaluated by standard MTT assay.