2α,9α,10β-triacetyl taxicin-I | 158137-46-3

• 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: 2α,9α,10β-triacetyl taxicin-I
• 英文别名: triacetyl-5-decinnamoyl taxicin I；triacetyl-5-decinnamoyltaxicine I；triacetyl-5-decinnamoyltaxicin I；5-hydroxytriacetyltaxicin I；5-hydroxytriacetyltaxicin-I；2,9,10-triacetyltaxicin-I；[(1S,2S,3R,5S,8R,9R,10R)-2,9-diacetyloxy-1,5-dihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxo-10-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• CAS: 158137-46-3
• 化学式: C₂₆H₃₆O₉
• 分子量: 492.566
• InChiKey: HMVNDOFAGCGZSA-OPHIHEFFSA-N

物化性质

• 沸点：
  588.5±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2α,9α,10β-triacetyl taxicin-I 在 吡啶 、 四氧化锇 、 四丁基氟化铵 、 sodium methylate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 46.17h， 生成 (3aS,7aR,10aR,10bR,13S,14S,14aR,14bS)-13,14-dihydroxy-14-(hydroxymethyl)-6,10b,15,15-tetramethyl-10a,10b,11,12,13,14,14a,14b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d:5,6-d']bis([1,3]dioxole)-2,5,9(7aH)-trione
  参考文献：
  名称：

  The Synthesis and Biological Activity of 9- and 2′-cAMP 7-Deoxypaclitaxel Analogues from 5-Cinnamoyltriacetyltaxicin-I

  摘要：

  The synthesis and biological activity of new 7-deoxypaclitaxel analogues 3 and 4 in which the hydroxy group at C-2' of the sidechain, C-9 and C-10 in the B-ring are substituted by cAMP and benozoyloxy group respectively are presented. These derivatives have been first synthesized from a natural taxoid 5-cinnamoyltriacetyltaxicin-1 5 and tested in vitro for cytotoxicity against three human tumor cell lines. The biologically tested results indicate 3 having more potent cytotoxicity and 4 having a remarkably reduced cytotoxicity as well as 33 having no much effect on cytotoxicity against all human tumor cell lines tested in comparison to that of paclitaxel. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00073-9
• 作为产物：
  描述：

  2,9,10-triacetyl-5-O-cinnamoyltaxicin-I 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以70%的产率得到2α,9α,10β-triacetyl taxicin-I
  参考文献：
  名称：

  The Synthesis and Biological Activity of 9- and 2′-cAMP 7-Deoxypaclitaxel Analogues from 5-Cinnamoyltriacetyltaxicin-I

  摘要：

  The synthesis and biological activity of new 7-deoxypaclitaxel analogues 3 and 4 in which the hydroxy group at C-2' of the sidechain, C-9 and C-10 in the B-ring are substituted by cAMP and benozoyloxy group respectively are presented. These derivatives have been first synthesized from a natural taxoid 5-cinnamoyltriacetyltaxicin-1 5 and tested in vitro for cytotoxicity against three human tumor cell lines. The biologically tested results indicate 3 having more potent cytotoxicity and 4 having a remarkably reduced cytotoxicity as well as 33 having no much effect on cytotoxicity against all human tumor cell lines tested in comparison to that of paclitaxel. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00073-9

文献信息

• Novel Dimeric Taxoids via Highly Regio- and Stereospecific Diels–Alder Cycloadditions of Taxinine B and Taxicine I Derivatives
  作者：Qian Cheng、Takayuki Oritani、Tohru Horiguchi、Teiko Yamada、Alfred Hassner

  DOI：10.1016/s0040-4020(00)00007-7

  日期：2000.2

  through regio- and stereospecific hetero Diels–Alder cycloaddition. Similar hetero Diels–Alder reaction of 4:5,6:7-diene aldehyde 13 gave two new dimeric taxoids 14 and 15. In addition, Lewis acid-catalyzed Diels–Alder reaction of 20-hydroxy-4:5,6:7-diene taxoid 12 with N-methylmaleimide led to cycloadduct exo-16 and γ-butyrolactone endo-17, while a similar Lewis acid-catalyzed Diels–Alder reaction of 12

  通过四个步骤氧化天然紫杉醇紫杉碱B衍生的20-羟基-4,5-烯-7-氧代毒素4产生相应的醛5，该醛通过区域和立体有规杂Diels-Alder环加成反应提供了新的二聚紫杉烷6。4：5,6：7-二烯醛13的类似杂Diels-Alder反应产生了两个新的二聚类紫杉醇14和15。5,6：：20-羟基-4另外，路易斯酸催化的Diels-Alder反应7 -二烯紫杉烷12与Ñ -methylmaleimide导致环加成外型- 16和γ丁内酯内切- 17，而类似的路易斯酸催化的12与紫杉烷7a的Diels-Alder反应仅产生环加合物exo - 18。如图7a和7b所示，醇4的两个异构体在氯化二乙基铝的存在下通过高度立体选择性的迈克尔加成反应生成了两个5-乙基取代的衍生物8和9。通过包括2D NMR研究在内的光谱实验确定了二聚体的结构和立体化学。
• Taxanes of the needles of Taxus x media
  作者：Koppaka V. Rao、G.Chandrasekhara Reddy、John Juchum

  DOI：10.1016/0031-9422(96)00281-6

  日期：1996.9

  chloroform-soluble portion of the methanolic extract of the needles of Taxus x media was chromatographed on a C-18 reverse-phase column and the major components were separated by direct crystallization. Further fractionation by chromatography on normal phase silica gel, of the filtrates from the region surrounding brevifoliol, yielded two taxanes belonging to the 2(3 → 20)abeo-taxane group, one of the

  紫杉 x 培养基针叶甲醇提取物的氯仿可溶部分在 C-18 反相柱上进行色谱分离，主要成分通过直接结晶分离。通过正相硅胶色谱法对来自短叶醇周围区域的滤液进行进一步分馏，得到了属于 2(3 → 20) abeo-taxane 组的两种紫杉烷，其中一种是taxinine M, 10 -脱乙酰紫杉醇、10-脱乙酰紫杉醇-7-木糖苷、10-脱乙酰紫杉醇-C-7-木糖苷、芹菜素和对羟基苯甲醛。
• Synthetic Studies Towards Taxol Analogs: Chemoselective Cleavage of C-5 Cinnamoyl Group in Taxane Group of Diterpenoids with Hydroxylamine
  作者：Yadagiri Bathini、Ronald G. Micetich、Mohsen Daneshtalab

  DOI：10.1080/00397919408010151

  日期：1994.6

  Taxane group of diterpenoids 2 and 3 which possess cinnamoyl moiety at C-5 position underwent selective cleavage to C-5 hydroxy compounds 4 and 5 on treatment with hydroxylamine. The resulting compounds were characterised based on their spectral data.
• (iPrO)3TiCl-induced reactions of α- and β-4(20)-epoxy-5-hydroxytriacetyltaxicin I
  作者：Qian Cheng、Takayuki Oritani、Tohru Horiguchi

  DOI：10.1016/s0040-4020(99)00707-3

  日期：1999.10

  Chlorolitanium triisopropoxide-induced reaction of alpha-4(20)-epoxy-5-hydroxytriacetyltaxicin I 2 gave a 4-hydroxymethylene-5-one 4 and a 4-hydroxy-4-chloromethylene 5, while the corresponding beta-4(20)-epoxide 3 gave a 3,8-cyclopropane 6 and a 6/8/5 ring system 7. Moreover, boron trifluoride-induced reaction of the a-4(20)epoxide 2 yielded a 6/8/6/7 ring system 8 and an A-ring contracted alcohol derivative 9. Plausible mechanisms of these reactions are proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

表征谱图