C-norpaclitaxel | 171021-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: C-norpaclitaxel
• 英文别名: [(1S,2S,3R,4S,7R,8R,9S,11R,14S)-4,11-diacetyloxy-14-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,8-dihydroxy-9,13,16,16-tetramethyl-10-oxo-6-oxatetracyclo[10.3.1.03,9.04,7]hexadec-12-en-2-yl] benzoate
• CAS: 171021-21-9
• 化学式: C₄₆H₄₉NO₁₄
• 分子量: 839.893
• InChiKey: QPZAABVYCBMYHU-PVRCWBQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  61
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  221
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2'-O-(叔-丁基二甲基硅烷基)紫杉醇 在 lead(IV) acetate 、 四氧化锇 、 三氟甲磺酸酐 、 氢氟酸 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 吡啶 、 苯 为溶剂， 生成 C-norpaclitaxel
  参考文献：
  名称：

  Synthesis of novel taxol analogs and evaluation of their biological activities

  摘要：

  Two new taxol analogs 6 and 10 have been prepared from baccatin III (1) and taxol (7a), respectively. Like taxol, both compounds were found to promote microtubule formation and stabilization, although they were less active than taxol. Both 6 and 10 exhibited cytotoxicity against J774.2 cells; 6 was similar to 60-fold less active and 10 was similar to 15-fold less active. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00337-5

文献信息

• Synthesis, structure elucidation and biological evaluation of C-norpaclitaxel
  作者：Xian Liang、David G.I. Kingston、Byron H. Long、Craig A. Fairchild、Kathy A. Johnston

  DOI：10.1016/0040-4039(95)01650-7

  日期：1995.10

  2′-TBDMS-6α-hydroxy-7-epipaclitaxel (1) with lead tetraacetate furnished 2′-TBDMS-C-norpaclitaxel (2) and the C-seco compound 3. Deprotection of 2 with pyridinium hydrofluoride yielded Cnorpaclitaxel (4). C-norpaclitaxel (4) is less effective at promoting the assembly of microtubules and less cytotoxic towards HCT116 cells than paclitaxel.

  用四乙酸铅将2'-TBDMS-C-正紫杉醇（2）和C-seco化合物氧化2'-TBDMS-6α-羟基-7-表紫杉醇（1）和C-seco化合物3。用氢氟吡啶鎓对2进行脱保护得到Cnorpaclitaxel（4）。与紫杉醇相比，C-诺紫杉醇（4）在促进微管组装方面效果不佳，对HCT116细胞的细胞毒性也较小。
• Paclitaxel analogs modified in ring C: Synthesis and biological evaluation
  作者：Xian Liang、David G.I. Kingston、Byron H. Long、Craig A. Fairchild、Kathy A. Johnston

  DOI：10.1016/s0040-4020(97)00074-4

  日期：1997.3

  Lead tetracetate oxidation of 6 alpha-hydroxy-7-epi-paclitaxel leads to C-nor-paclitaxel and C-seco-paclitaxel derivatives. Tetrapropylammonium permthenate (TPAP) oxidation of a 6 alpha-hydroxy-7-epi-paclitaxel derivative leads to a 6-formyl-C-nor-paclitaxel derivative. Reaction of a 6 alpha-O-trifluoromethanesulfonyl-7-epi-paclitaxel derivative with DMAP yields a 20-O-acetyl-4-deacetyl-5,6-dehydro-6-formyl-C-nor-paclitaxel derivative. C-nor-paclitaxel analogs are less active than paclitaxel. (C) 1997 Elsevier Science Ltd.