2-去乙酰氧-5Α-羟基紫杉宁J | 87193-98-4

• 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
• 中文名称: 2-去乙酰氧-5Α-羟基紫杉宁J
• 英文名称: acetic acid 7,10,13-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0(3,8)]pentadec-11-en-9-ylester
• 英文别名: 2-deacetoxy-5-decinnamoyltaxinine J；2-deacetoxy-5-decinamoyltaxinine J；2-deacetoxy-decinnamoil taxinine J；2-deacetoxydecinnamoyltaxinine J；2-deacetoxydecinnamoyltaxinine-J；[(1R,3R,5S,7S,8S,9R,10R,13S)-7,9,10-triacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• CAS: 87193-98-4
• 化学式: C₂₈H₄₀O₉
• 分子量: 520.62
• InChiKey: WOKHREABHMWBBE-CNZAUHOSSA-N

物化性质

• 熔点：
  188-189 °C
• 沸点：
  565.8±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-去乙酰氧-5Α-羟基紫杉宁J 在 lithium hydroxide 、 吡啶 、 chromium(VI) oxide 作用下， 以 甲醇 、 水 、 二氯甲烷 为溶剂， 反应 3.25h， 以55%的产率得到taxuspinanane K
  参考文献：
  名称：

  Microbial and reducing agents catalyze the rearrangement of taxanes

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(01)00106-7
• 作为产物：
  描述：

  2'-deacetoxyaustrospicatine 在 硫酸羟胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 54.0h， 生成 2-去乙酰氧-5Α-羟基紫杉宁J
  参考文献：
  名称：

  氮杂环丁烷型紫杉烷的合成

  摘要：

  从生物碱2'-脱乙酰氧基奥古斯汀碱（2）开始，合成氧杂环丁烷型紫杉烷1-脱氧-2-脱苯甲酰氧基-4-脱乙酰浆果赤霉素VI的氮杂环丁烷等排体。

  DOI：

  10.1016/0040-4039(96)00495-9

文献信息

• In vitro and in vivo anticancer activity of 2-deacetoxytaxinine J and synthesis of novel taxoids and their in vitro anticancer activity☆
  作者：K. Papi Reddy、Hemant K. Bid、V. Lakshma Nayak、Preeti Chaudhary、J.P. Chaturvedi、K.R. Arya、Rituraj Konwar、T. Narender

  DOI：10.1016/j.ejmech.2009.04.022

  日期：2009.10

  line (HEK-293) has been studied. 2-DAT-J (1) showed significant in vitro activity against breast cancer cell line at a concentration of 20 μM and 10 μM in MCF-7 and MDA-MB-231 respectively. Few novel taxoids were derived (7, 8 and 10–13) from the naturally occurring 2-DAT-J (1) and screened for their anticancer activity. The structure–activity relationship studies indicated that the cinnamoyl group

  紫杉烷二萜类化合物2-脱乙酰氧基紫杉碱J（2-DAT-J）1已从喜马拉雅紫杉（Taxus baccata L.spp。）的树皮中分离。已经研究了以合理的良好收率（0.1％）制备的Wallichiana及其对乳腺癌细胞系（MCF-7和MDA-MB-231）和正常人肾上皮细胞系（HEK-293）的抗癌活性。2-DAT-J（1）在MCF-7和MDA-MB-231中分别以20μM和10μM的浓度显示出对乳腺癌细胞株的显着体外活性。几个新颖的紫杉烷类，推导（7，8和10 - 13）从天然存在的2-DAT-J（1）并筛选其抗癌活性。结构-活性关系研究表明，C-5上的肉桂酰基和C-10上的乙酰基对于抗癌活性至关重要。还对2-DAT-J（1）在初次雌性Sprague DAwley大鼠中以口服剂量10 mg / kg体重对DMBA诱导的乳腺肿瘤进行了30天的体内活性测试，结果显示：与媒介物治疗组相比（p  <0
• 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.
• Chemical Oxidation of Taxoids with m-CPBA and Dimethyl Dioxirane: Regioselective Epoxidation of Taxinine J Derivatives
  作者：Takayuki Oritani、Tohru Horiguchi、Masanori Nagura、Qian Cheng、Toshio Kudo

  DOI：10.3987/com-00-8929

  日期：——
• 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.
• An Unprecedented Biogenetic-Type Chemical Synthesis of 1(15→11) Abeotaxanes from Normal Taxanes
  作者：T. Narender、K. Papi Reddy、V. K. Singh、K. Rajendar、J. Sarkar

  DOI：10.1021/np900722j

  日期：2010.4.23

  A one-pot chemical process using BF(3)center dot Et(2)O for the synthesis of a new class of 1(15 -> 11) abeotaxanes from normal taxanes has been developed. The chemical structures of rearranged 1(15 -> 11) abeotaxane were established by extensive 2D NMR spectroscopic data.

表征谱图