4β-[O-methyl(ortho-iodophenyl-1,2,3-triazol-4yl)]epipodophyllotoxin | 1600500-34-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 4β-[O-methyl(ortho-iodophenyl-1,2,3-triazol-4yl)]epipodophyllotoxin
• CAS: 1600500-34-2
• 化学式: C₃₁H₂₈IN₃O₈
• 分子量: 697.483
• InChiKey: IJBUPHVOAVIHNU-GVGYXHIPSA-N

物化性质

• 熔点：
  183-187 °C
• 沸点：
  782.5±70.0 °C(predicted)
• 密度：
  1.70±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  112.39
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  2-碘苯胺 在 盐酸 、 copper(ll) sulfate pentahydrate 、 L-ascorbic acid sodium 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.5h， 生成 4α-[O-methyl(ortho-iodophenyl-1,2,3-triazol-4yl)]podophyllotoxin 、 4β-[O-methyl(ortho-iodophenyl-1,2,3-triazol-4yl)]epipodophyllotoxin
  参考文献：
  名称：

  A convergent synthesis of alkyne–azide cycloaddition derivatives of 4-α,β-2-propyne podophyllotoxin depicting potent cytotoxic activity

  摘要：

  A facile synthetic approach to construct the O-propargyl derivatives of 4 alpha and 4 beta-(1,2,3-triazol-4-yl)-podophyllotoxin (9a-k & 10a-k) and 4 '-Demethy1-4 '-4 beta-(1,2,3-triazol-4-yl)-epipodophyllotoxin (12a-d) were synthesized by means of click chemistry. The chemical structures were confirmed by H-1, C-13, 2D NMR and HRMS spectral analysis and their cytotoxicities were measured against diverse human cancer cell lines viz. PC-3, PANC-1, COLO-205 and A-549 by MU assay. Some of the compounds were found more potent than the parent molecule Podophyllotoxin, like; 9a & 10a, 9h & 10h, 9k & 10k, 10d, 8 and 12a. The most potent molecule discovered was compound 9k that exhibited the highest cytotoxicity on all the four cancer cell lines with IC50 values of 3.8-22 nM. The compound further found to induce apoptosis and strongly hindered the motility of aggressive prostate cancer PC-3 cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.030