7-deoxypaclitaxel | 149705-85-1

• 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: 7-deoxypaclitaxel
• 英文别名: paclitaxel；7-Deoxytaxol；[(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]heptadec-13-en-2-yl] benzoate
• CAS: 149705-85-1
• 化学式: C₄₇H₅₁NO₁₃
• 分子量: 837.921
• InChiKey: KNDOYLWKJXBKBV-ABSZOUAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  61
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  7-deoxypaclitaxel 在 二氮烯 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 10-deacetoxy-paclitaxel
  参考文献：
  名称：

  Synthesis of a novel C-10 spiro-epoxide of paclitaxel

  摘要：

  New analogues of paclitaxel (1a, active constituent of Taxol((R))) were synthesized containing an epoxide at the C-10 position. The introduction of the epoxide was carried out by selective removal of the C10-acetate followed by protection of the C2 ' -and C7-hydroxyl groups. After oxidation to yield a ketone at the C10-position, this intermediate was reacted with dimethylsulfonium ylide. Deprotection and further manipulations provide the C10-spiro epoxide of paclitaxel (1b) and the corresponding C7-MOM ether (1c). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00280-3
• 作为产物：
  描述：

  (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-9,11-dihydroxy-4a,8,13,13-tetramethyl-4-(((methylthio)carbonothioyl)oxy)-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate 在 咪唑 、 盐酸 、 正丁基锂 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成 7-deoxypaclitaxel
  参考文献：
  名称：

  Synthesis of 7-deoxy- and 7,10-dideoxytaxol via radical intermediates

  摘要：

  7-Deoxytaxol and 7,10-dideoxytaxol were prepared from baccatin III, employing the Barton deoxygenation procedure and the Holton acylation method at C-13.

  DOI：

  10.1021/jo00071a002

文献信息

• An efficient semisynthesis of 7-deoxypaclitaxel from taxine
  作者：Radomir Matović、Radomir N. Saičić

  DOI：10.1039/a803990i

  日期：——

  Highly cytotoxic 7-deoxypaclitaxel analogues are obtained by a semisynthesis starting from taxine—the most abundant naturally occurring taxane diterpene fraction.

  高细胞毒性的 7-脱氧紫杉醇类似物是从紫杉素--天然存在的最丰富的紫杉烷二萜成分--开始的一种半合成方法获得的。
• Taxane anticancer agents
  申请人：——

  公开号：US20020016356A1

  公开（公告）日：2002-02-07

  The present invention concerns novel 7-deoxy taxane derivatives, their use as antitumor agents, and pharmaceutical formulations.

  本发明涉及新型7-去氧紫杉烷衍生物，其作为抗肿瘤剂的用途以及制药配方。
• Modified taxols. 10. Preparation of 7-deoxytaxol, a highly bioactive taxol derivative, and interconversion of taxol and 7-epi-taxol
  作者：Ashok G. Chaudhary、John M. Rimoldi、David G. I. Kingston

  DOI：10.1021/jo00067a008

  日期：1993.7

  Deoxygenation of taxol at C-7 can be achieved through its S-methyldithiocarboxy derivative 3 to yield a product which is more cytotoxic than-taxol to P-388 cells.
• Synthesis and interactions of 7-deoxy-, 10-deacetoxy, and 10-deacetoxy-7-deoxypaclitaxel with NCI/ADR-RES cancer cells and bovine brain microvessel endothelial cells
  作者：Haibo Ge、Veena Vasandani、Jacquelyn K. Huff、Kenneth L. Audus、Richard H. Himes、Anna Seelig、Gunda I. Georg

  DOI：10.1016/j.bmcl.2005.09.043

  日期：2006.1

  7-Deoxypaclitaxel, 10-deacetoxypaclitaxel and 10-deacetoxy-7-deoxypaclitaxel were prepared and evaluated for their ability to promote assembly of tubulin into microtubules, their cytotoxicity against NCI/ADR-RES cells and for their interactions with P-glycoprotein in bovine brain microvessel endothelial cells. The three compounds were essentially equivalent to paclitaxel in cytotoxicity against NCI/ADR-RES cells. They also appeared to interact with P-glycoprotein in the endothelial cells with the two 10-deacetoxy compounds having less interaction than paclitaxel and 7-deoxypaclitaxel. (c) 2005 Elsevier Ltd. All rights reserved.
• Saicic, Radomir N.; Matovic, Radomir, Journal of the Chemical Society. Perkin transactions I, 2000, # 1, p. 59 - 66
  作者：Saicic, Radomir N.、Matovic, Radomir

  DOI：——

  日期：——