2-去乙酞氧基紫杉素J | 119347-14-7

• 物质功能分类: 天然产物 - 萜类
• 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-去乙酞氧基紫杉素J
• 英文名称: 2-desacetoxytaxinine J
• 英文别名: 2-deacetoxytaxinine J；[(1R,3R,5S,7S,8S,9R,10R,13S)-7,9,10,13-tetraacetyloxy-8,12,15,15-tetramethyl-4-methylidene-5-tricyclo[9.3.1.03,8]pentadec-11-enyl] (E)-3-phenylprop-2-enoate
• CAS: 119347-14-7
• 化学式: C₃₇H₄₆O₁₀
• 分子量: 650.766
• InChiKey: MIJTXBNFQDJTPL-PXORYUGNSA-N

物化性质

• 熔点：
  169-171℃
• 沸点：
  673.8±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-去乙酞氧基紫杉素J 在 lithium hydroxide 、 羟胺 、 sodium acetate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 27.25h， 生成 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 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 生成 2-去乙酞氧基紫杉素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

• Synthesis of azetidine-type taxanes
  作者：Ivana Fenoglio、Gian Mario Nano、David G. Vander Velde、Giovanni Appendino

  DOI：10.1016/0040-4039(96)00495-9

  日期：1996.4

  Starting from the alkaloid 2′-deacetoxyaustrospicatine (2) azetidine isosteres of the oxetane-type taxane 1-deoxy-2-debenzoyloxy-4-deacetylbaccatin VI were synthesised.

  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。
• 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
• Reanalysis of the biotransformation of 4(20),11(12)-taxadiene derivatives
  作者：Di-An Sun、Françoise Sauriol、Orval Mamer、Lolita O Zamir

  DOI：10.1139/v01-125

  日期：2001.9.1

  Reanalysis of the biotransformation of 4(20),11(12)-taxadiene derivatives by Absidia coerulea ATCC 10738a unravelled additional unprecedented rearrangement reactions. 5α,7β,9α,10β,13α-pentaacetoxy-4(20),11(12)-taxadiene (1) was converted to 10 new minor taxane derivatives in addition to the previously reported C-1, C-14-hydroxylations and C-15-hydroxylated abeo-taxane. In addition, 2-deacetoxytaxinine J (2) was successfully metabolized with the same fungi.Key words: natural products, terpenes and terpenoids, microorganism, oxygenation, rearrangement.

  Absidia coerulea ATCC 10738a重新分析了4（20），11（12）-紫杉烯衍生物的生物转化，揭示了额外的前所未有的重排反应。5α，7β，9α，10β，13α-五乙酰氧基-4（20），11（12）-紫杉烯（1）被转化为10个新的次要紫杉烷衍生物，除了先前报道的C-1，C-14-羟基化和C-15-羟基化的abeo-紫杉烷。此外，2-去乙酰基紫杉烷J（2）也成功地被同一种真菌代谢。关键词：天然产物，萜类化合物，微生物，氧化，重排。
• 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.
• Biotransformation of a 4(20),11(12)-taxadiene derivative
  作者：Di-An Sun、Françoise Sauriol、Orval Mamer、Lolita O. Zamir

  DOI：10.1016/s0968-0896(00)00299-6

  日期：2001.3

  A 4(20),11(12)-taxadiene derivative was converted to hydroxylated derivatives by Cunninghamella elegans AS3.2033 and Cunninghamella elegans var chibaensis ATCC 20230. Both microorganisms led to C-1 hydroxylations and conversion to a C-15-hydroxylated abeo-taxane. Additional products from the two fungi differed: a C-14 oxidation and a trans-cis isomerization of the cinnamoyl for one and an unprecedented hydroxylation at C-17 for the other. (C) 2001 Elsevier Science Ltd. All rights reserved.