| 202996-26-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 202996-26-7
• 化学式: C₅₇H₈₆N₂O₁₃Si₂
• 分子量: 1063.49
• InChiKey: KFAAWSXIRJSWNA-BONWXTTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.28
• 重原子数：
  74.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  194.25
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 氢氟酸 作用下， 以 吡啶 、 乙腈 为溶剂， 生成 14-nor-seco-10-deacetylbaccatin III 13-[N-(tert-butoxycarbonyl)-(2'R,3'S)-3'-phenylisoserinamide]
  参考文献：
  名称：

  Syntheses and Structure−Activity Relationships of Novel Nor-seco Taxoids

  摘要：

  A series of novel nor-seco taxoids (4a-b, 5a-d, 6), including either a C-13 ester linkage or a C-13 amide linkage, was synthesized by means of the p-lactam synthon method using the coupling of (3R,4S)-1-acyl-beta-lactams with properly protected nor-seco baccatin III derivatives (1, 2, 3) as the key step. Nor-seco baccatin III derivatives were prepared through oxidative cleavage of the A ring of 14 beta-hydroxy-10-deacetylbaccatin III followed by reduction, amination using Mitsunobu conditions, or reductive amination. Nor-seco taxoids with a C-13 ester linkage (4a-b) or a C-13 N-Me amide linkage (6) show reduced cytotoxicity against human cancer cell lines as compared with paclitaxel, but still retain a certain level of activity despite the destruction of the taxane A ring. However, none of the analogues with a C-13 N-H amide linkage (5a-d) exhibit appreciable activity (IC50 > 1.0 mu M). A restrained molecular dynamics study reveals the inability of 5a-d to attain the proposed bioactive conformation, which accounts for the loss of activity.

  DOI：

  10.1021/jo971953r
• 作为产物：
  描述：

  7-(triethylsilyl)-13-formyl-14-nor-seco-10-deacetylbaccatin III 在 sodium cyanoborohydride 、 三苯基膦 、 甲胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 42.33h， 生成
  参考文献：
  名称：

  Syntheses and Structure−Activity Relationships of Novel Nor-seco Taxoids

  摘要：

  A series of novel nor-seco taxoids (4a-b, 5a-d, 6), including either a C-13 ester linkage or a C-13 amide linkage, was synthesized by means of the p-lactam synthon method using the coupling of (3R,4S)-1-acyl-beta-lactams with properly protected nor-seco baccatin III derivatives (1, 2, 3) as the key step. Nor-seco baccatin III derivatives were prepared through oxidative cleavage of the A ring of 14 beta-hydroxy-10-deacetylbaccatin III followed by reduction, amination using Mitsunobu conditions, or reductive amination. Nor-seco taxoids with a C-13 ester linkage (4a-b) or a C-13 N-Me amide linkage (6) show reduced cytotoxicity against human cancer cell lines as compared with paclitaxel, but still retain a certain level of activity despite the destruction of the taxane A ring. However, none of the analogues with a C-13 N-H amide linkage (5a-d) exhibit appreciable activity (IC50 > 1.0 mu M). A restrained molecular dynamics study reveals the inability of 5a-d to attain the proposed bioactive conformation, which accounts for the loss of activity.

  DOI：

  10.1021/jo971953r