5α,13α-dihydroxy-7β,9α,10β-triacetoxy-4(20),11-taxadiene | 119777-85-4

• 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: 5α,13α-dihydroxy-7β,9α,10β-triacetoxy-4(20),11-taxadiene
• 英文别名: [(1R,3R,5S,7S,8S,9R,10R,13S)-9,10-diacetyloxy-5,13-dihydroxy-8,12,15,15-tetramethyl-4-methylidene-7-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• CAS: 119777-85-4
• 化学式: C₂₆H₃₈O₈
• 分子量: 478.583
• InChiKey: QOBXWLOLBBKDAU-ONRBSIPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5α,13α-dihydroxy-7β,9α,10β-triacetoxy-4(20),11-taxadiene 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲苯 为溶剂， 生成 2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-[7,9,10-triacetoxy-8,12,15,15-tetramethyl-4-methylene-5-(3-phenyl-acryloyloxy)-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl] ester
  参考文献：
  名称：

  Synthesis and biological evaluation of new taxoids derived from 2-deacetoxytaxinine J

  摘要：

  A small library of 2-deacetoxytaxinine J (DAT-J) 1 derivatives was synthesised and tested in vitro for their reversal activity in human mammary carcinoma MDR cell line MCF7-R. One of the new taxoids showed to be active at 0. 1 mu M when tested in combination with paclitaxel. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.101
• 作为产物：
  描述：

  苯丙酸,a-(乙酰氧基)-b-(二甲氨基)-,1,8,11,12-四(乙酰氧基)-1,2,3,4,4a,5,6,7,8,11,12,12a-十二氢-9,12a,13,13-四甲基-4-亚甲基-6,10-亚甲基苯并环癸烯-3-基酯(9CI) 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 5α,13α-dihydroxy-7β,9α,10β-triacetoxy-4(20),11-taxadiene
  参考文献：
  名称：

  Ettouati, Laurent; Ahond, Alain; Convert, Odile, Bulletin de la Societe Chimique de France, 1988, # 4, p. 749 - 755

  摘要：

  DOI：

文献信息

• Synthesis of paclitaxel (docetaxel) / 2-deacetoxytaxinine J dimers
  作者：Giovanni Appendino、Emanuela Belloro、Sven Jakupovic、Bruno Danieli、Jasmin Jakupovic、Ezio Bombardelli

  DOI：10.1016/s0040-4020(99)00290-2

  日期：1999.5

  Starting from taxanes available in multigram amounts from widespread ornamental yews (10-deacetylbaccatin III (4) and 2'-deacetoxyaustrospicatine (5)), two dimeric taxoids (3a, 3b) with potential dual target specificity (beta-tubulin and P-gp) were synthesised. Both compounds lacked significant cytotoxicity, though 3b retained a strong activity in the tubulin depolimerisation assay. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Microbial and reducing agents catalyze the rearrangement of taxanes
  作者：Di-An Sun、Anastasia Nikolakakis、Françoise Sauriol、Orval Mamer、Lolita O. Zamir

  DOI：10.1016/s0968-0896(01)00106-7

  日期：2001.8

  5 alpha, 7 beta, 9 alpha, 10 beta, 13 alpha -Pentahydroxy-4(20),11(12)-taxadiene derivative 1 was converted to two unprecedented 1(15 --> 11)abeo-taxanes and a taxane derivative with a C10-C11 double bond by Absidia coerula ATCC 10738a. A similar compound was obtained from treatment with zinc of a triacetoxy-4(20),11(12)-taxadiene derivative. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and biological evaluation of new taxoids derived from 2-deacetoxytaxinine J
  作者：Maurizio Botta、Silvia Armaroli、Daniele Castagnolo、Gabriele Fontana、Paula Pera、Ezio Bombardelli

  DOI：10.1016/j.bmcl.2006.12.101

  日期：2007.3

  A small library of 2-deacetoxytaxinine J (DAT-J) 1 derivatives was synthesised and tested in vitro for their reversal activity in human mammary carcinoma MDR cell line MCF7-R. One of the new taxoids showed to be active at 0. 1 mu M when tested in combination with paclitaxel. (c) 2007 Elsevier Ltd. All rights reserved.
• Ettouati, Laurent; Ahond, Alain; Convert, Odile, Bulletin de la Societe Chimique de France, 1988, # 4, p. 749 - 755
  作者：Ettouati, Laurent、Ahond, Alain、Convert, Odile、Laurent, Dominique、Poupat, Christiane、Potier, Pierre

  DOI：——

  日期：——