2,3,4,7-tetraacetoxy-10b-(R)-hydroxypancratistatin | 160429-69-6

• 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: 2,3,4,7-tetraacetoxy-10b-(R)-hydroxypancratistatin
• 英文别名: 10b(R)-hydroxy-2,3,4,7-tetra-O-acetylpancratistatin；[(1S,2S,3S,4S,4aS,11bR)-2,4,7-triacetyloxy-1,11b-dihydroxy-6-oxo-1,2,3,4,4a,5-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-3-yl] acetate
• CAS: 160429-69-6
• 化学式: C₂₂H₂₃NO₁₃
• 分子量: 509.424
• InChiKey: QSFQXYRJJPGFPX-WUERDQBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  193
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3,4,7-tetraacetoxy-10b-(R)-hydroxypancratistatin 以 吡啶 为溶剂， 反应 12.0h， 生成 10b(R),N,7-O-methyloxalyl-1,2,3,4-tetra-O-acetylpancratistatin
  参考文献：
  名称：

  Antineoplastic Agents. 550. Synthesis of 10b(S)-Epipancratistatin from (+)-Narciclasine^,1

  摘要：

  By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.

  DOI：

  10.1021/np068046e
• 作为产物：
  描述：

  水仙环素 在 四氧化锇 、 dihydroquinine 4-chlorobenzoate 、 N-甲基吗啉氧化物 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,3,4,7-tetraacetoxy-10b-(R)-hydroxypancratistatin
  参考文献：
  名称：

  Synthesis of 10b-R-hydroxy-pancratistatin via narciclasine

  摘要：

  从 narciclasine 1 中实现了 10b-R-hydroxy-pancratistatin 3 的非对映选择性合成。

  DOI：

  10.1039/c39940002725

文献信息

• Synthesis of 10b-R-hydroxy-pancratistatin via narciclasine
  作者：George R. Pettit、Noeleen Melody、Michael O'Sullivan、Michael A. Thompson、Delbert L. Herald、Brian Coates

  DOI：10.1039/c39940002725

  日期：——

  A diastereoselective synthesis of 10b-R-hydroxy-pancratistatin 3 from narciclasine 1 has been achieved.

  从 narciclasine 1 中实现了 10b-R-hydroxy-pancratistatin 3 的非对映选择性合成。
• Synthesis of 10b(R)-Hydroxypancratistatin, 10b(S)-Hydroxy-1-epipancratistatin, 10b(S)-Hydroxy-1,2-diepipancratistatin and Related Isocarbostyrils
  作者：George R. Pettit、Noeleen Melody、Delbert L. Herald、Jean M. Schmidt、Robin K. Pettit、Jean-Charles Chapuis

  DOI：10.3987/com-01-s(k)7

  日期：——
• Antineoplastic Agents. 550. Synthesis of 10b(<i>S</i>)-Epipancratistatin from (+)-Narciclasine^,1
  作者：George R. Pettit、Noeleen Melody、Delbert L. Herald、John C. Knight、Jean-Charles Chapuis

  DOI：10.1021/np068046e

  日期：2007.3.1

  By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.