Δ^6,7-paclitaxel | 158830-49-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Δ^6,7-paclitaxel
• 英文别名: 7-deoxy-Δ^6,7-paclitaxel；[(1S,2S,3R,4S,7R,10R,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadeca-8,13-dien-2-yl] benzoate
• CAS: 158830-49-0
• 化学式: C₄₇H₄₉NO₁₃
• 分子量: 835.905
• InChiKey: COFONBOOKDFTHL-ABSZOUAASA-N

物化性质

• 沸点：
  930.077±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.379±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  61
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  201
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Δ^6,7-paclitaxel 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以95%的产率得到6,7-epoxy-paclitaxel
  参考文献：
  名称：

  Menichincheri, Maria; Botta, Maurizio; Ceccarelli, Walter, Medicinal Chemistry Research, 1995, vol. 5, # 7, p. 534 - 556

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-O-acetyl-7α-paclitaxel 在 4-二甲氨基吡啶 、 sodium azide 、 二乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 Δ^6,7-paclitaxel
  参考文献：
  名称：

  Menichincheri, Maria; Botta, Maurizio; Ceccarelli, Walter, Medicinal Chemistry Research, 1995, vol. 5, # 7, p. 534 - 556

  摘要：

  DOI：

文献信息

• Crystallographic determination of the stereochemistry of C-6,7 epoxy paclitaxel
  作者：Thomas J. Altstadt、Qi Gao、Mark D. Wittman、John F. Kadow、Dolatrai M. Vyas

  DOI：10.1016/s0040-4039(98)00969-1

  日期：1998.7

  derivative to be 6α, 7α. Thus finding corrects the structure reported by Kingston et al based on NOE data and corrects the discrepancy reported for facial selectivity of the reaction of osmium tetroxide and dimethyldioxirane with the C-6,7 olefin of paclitaxel.

  通过浆果赤霉素的单晶X射线分析确定C-6，7环氧紫杉醇的立体化学为6α，7α。因此，发现纠正了金斯敦等人基于NOE数据报告的结构，并纠正了四氧化和二甲基二环氧乙烷与紫杉醇的C-6,7烯烃反应的面部选择性所报告的差异。
• Synthesis and biological evaluation of paclitaxel analogs modified in ring C
  作者：Xian Liang、David G.I. Kingston、Chii M. Lin、Ernest Hamel

  DOI：10.1016/0040-4039(95)00431-b

  日期：1995.4

  Both 7-deoxy-7 alpha-azidopaclitaxel (6) and 7-deoxy-Delta(6,7)-paclitaxel (4) can be prepared from paclitaxel-7-0-triflate (2b). Oxidation of 7-deoxy-Delta(6,7)-paclitaxel with dioxirane yields the epoxide 7, while oxidation with osmium tetroxide yields 6 alpha-hydroxy-7-epipaclitaxel (9), and acylation of this gives the 6 alpha-acyloxy-7-epipaclitaxel derivatives 11a-d. No compound was as effective at promoting tubulin assembly as paclitaxel, but most stabilized polymer as well as or better than paclitaxel. Compounds 4, 6, 7, 9, and 11d differed little from paclitaxel in their cytotoxicity for human Burkitt lymphoma CA46 cells.
• Synthesis of novel taxol analogs and evaluation of their biological activities
  作者：Paul A. Wender、Daesung Lee、Tapan K. Lal、Susan B. Horwitz、Srinivasa Rao

  DOI：10.1016/s0960-894x(97)00337-5

  日期：1997.7

  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.
• 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.