methyl ent-kaur-15-en-19-oate | 18671-79-9

• 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: methyl ent-kaur-15-en-19-oate
• 英文别名: methyl kaur-15-en-19-oate；Δ¹⁵-Kouren-19-saeuremethylester；(-)-Kauren-(15)-saeure-(19)-methylester；methyl (1S,4S,5R,9S,10S,13R)-5,9,14-trimethyltetracyclo[11.2.1.01,10.04,9]hexadec-14-ene-5-carboxylate
• CAS: 18671-79-9
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: NACOSXOOEICJJO-YXEXTMMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl ent-kaur-15-en-19-oate 在 lithium aluminium tetrahydride 作用下， 生成 (-)-Kaur-15-en-19-ol
  参考文献：
  名称：

  化学组成Xylopia aethiopica。一种新的二萜酸木糖二酸的结构

  摘要：

  从的干果Xylopia马蹄莲已分离出一种新的二萜酸，xylopic酸，其被示出为15β乙酰氧基- （ - ） -考尔-16-烯-19-酸。

  DOI：

  10.1039/j39680000311
• 作为产物：
  描述：

  kaurenoic acid 在 氟磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.58h， 生成 methyl ent-kaur-15-en-19-oate
  参考文献：
  名称：

  逆仿生转化法合成天然Atisane型二萜类化合物

  摘要：

  一种有效的一个步骤，复古-biomimetic过程对于具有atisane结构的天然产物的合成被描述（方案2），这是药用植物的部件和具有相关的生物活性的天然产物。通过化学转化和光谱数据证实了它们的结构。起始原料是已知的ent -kaur-16-en-19-oic酸（1）和ent -trchyloban-19-oic酸（2），即从向日葵废料中容易获得的二萜类化合物。

  DOI：

  10.1002/hlca.201200305

文献信息

• Synthesis and anti-inflammatory activity of ent-kaurene derivatives
  作者：Idaira Hueso-Falcón、Irene Cuadrado、Florencia Cidre、Juan M. Amaro-Luis、Ángel G. Ravelo、Ana Estevez-Braun、Beatriz de las Heras、Sonsoles Hortelano

  DOI：10.1016/j.ejmech.2011.01.052

  日期：2011.4

  inhibition of NF-κB activation might be the mechanism involved in anti-inflammatory effects of these kaurene derivatives. As expected, cytokines IL-6, IL-1α, TNF-α and IFN-γ were downregulated in the presence of compound 28, 55 and 62 after stimulation with LPS. These results indicate that kaurene derivatives might be used for the design of new anti-inflammatory agents.

  制备了一系列的贝壳杉烯衍生物（1 – 63），并评估了其抗炎活性。13种测试化合物能够抑制NO的产生，IC 50为2至10μM。化合物11，12，14和23显示细胞存活力的低百分比，而化合物9，10，17，28，37，48，55，61和62在浓度高达25μM时无细胞毒性。概述了一些结构-活动关系。化合物28，55和62，选择作为代表性的化合物，它们有效地抑制NOS-2蛋白的表达。我们还确定抑制NF-κB活化可能是这些贝壳杉烯衍生物的抗炎作用所涉及的机制。如所预期的，细胞因子IL-6，IL-1α，TNF-α和IFN-γ水平在化合物存在下调28，55和62用LPS刺激后。这些结果表明，kaurene衍生物可用于设计新的抗炎药。
• Fluorinated kaurenoids. Part 2. Preparation of methyl ent-17,17,17-trifluorokaur-15-en-19-oate and ent-16,16-difluoro-17-norkauran-19-oic acid from xylopic acid
  作者：Brian E. Cross、Anton Erasmuson、Paolino Filippone

  DOI：10.1039/p19810001293

  日期：——

  An attempt to convert methyl ent-16-oxo-17-norkauran-19-oate (3), derived from xylopic acid, into methyl ent-17,17-difluorokaur-16-en-19-oate failed. However, treatment of the norketone (3) with diethylaminosulphur trifluoride (DAST) gave methyl ent-16,16-difluoro-17-norkauran-19-oate (5). The latter afforded the corresponding acid (4) which was active as a growth promoter in a dwarf-rice bioassay

  尝试将源自木糖二酸的eNT甲基-16-oxo-17-norkauran-19-oate（3）转换为eNT -1,17-difluorokaur-16-en-19-oate甲基戊酸。然而，治疗norketone（3）用二乙基三氟化硫（DAST）的给甲基ENT -16,16二氟-17- norkauran-19 -酸酯（5）。后者提供了相应的酸（4），在矮米生物测定中可作为生长促进剂起作用。甲基deacetylxylopate（18）与DAST，然后由终端亚甲基的裂解处理，得到甲基ENT -15-氟-16-氧代-17- norkauran-19 -酸酯（15），其与二溴二氟甲烷和三（反应二甲基氨基）膦，得到，而不是预期的17,17-二氟烯烃（19），但甲基ENT-17,17,17-trifluorokaur-15-en-19-oate（28）收率不佳。用二酰亚胺还原草酰氯甲酯可立体定向得到16
• Synthesis, cytotoxicity and antiplasmodial activity of novel ent -kaurane derivatives
  作者：Ronan Batista、Pablo A. García、María Angeles Castro、José M. Miguel del Corral、Nivaldo L. Speziali、Fernando de P. Varotti、Renata C. de Paula、Luis F. García-Fernández、Andrés Francesch、Arturo San Feliciano、Alaíde B. de Oliveira

  DOI：10.1016/j.ejmech.2012.12.010

  日期：2013.4

  This paper reports on the syntheses and spectrometric characterisation of eleven novel ent-kaurane diterpenoids, including a complete set of H-1, C-13 NMR and crystallographic data for two novel ent-kaurane diepoxides. Moreover, the antineoplastic cytotoxicity for kaurenoic acid and the majority of ent-kaurane derivatives were assessed in vitro against a panel of fourteen cancer cell lines, of which allylic alcohols were shown to be the most active compounds. The good in vitro antimalarial activity and the higher selectivity index values observed for some ent-kaurane epoxides against the chloroquine-resistant W2 clone of Plasmodium falciparum indicate that this class of natural products may provide new hits for the development of antimalarial drugs. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis and induction of apoptosis signaling pathway of ent-kaurane derivatives
  作者：Idaira Hueso-Falcón、Natalia Girón、Pilar Velasco、Juan M. Amaro-Luis、Angel G. Ravelo、Beatriz de las Heras、Sonsoles Hortelano、Ana Estevez-Braun

  DOI：10.1016/j.bmc.2009.11.064

  日期：2010.2

  Thirty one ent-kaurane derivatives were prepared from kaurenoic acid (1), grandiflorenic acid (16), 15 alpha-acetoxykaurenoic acid (26) and 16 alpha-hydroxy-kaurenoic acid (31). They were tested for their ability to inhibit cell viability in the mouse leukemic macrophagic RAW 264.7 cell line. The most effective compounds were 12, 20, 21, and 23. These were selected for further evaluation in other human cancer cell lines such as Hela, HepG2, and HT-29. Similar effects were obtained although RAW 264.7 cells were more sensitive. In addition, these compounds were significantly less cytotoxic in non-transformed cells. The apoptotic potential of the most active compounds was investigated and they were able to induce apoptosis with compound 12 being the best inducer. The caspase-3, -8 and -9 activities were measured. The results obtained showed that compounds 12, 21, and 23 induce apoptosis via the activation of caspase-8, whereas compound 20 induces apoptosis via caspase-9. Immunoblot analysis of the expression of p53, Bax, Bcl-2, Bcl-xl, and IAPs in RAW 264.7 cells was also carried out. When cells were exposed to 5 mu M of the different compounds, expression levels of p53 and Bax increased whereas levels of antiapoptotic proteins such as Bc1-2, Bc1-x1, and IAPs decreased. In conclusion, kaurane derivatives (12, 20, 21, and 23) induce apoptosis via both the mitochondrial and membrane death receptor pathways, involving the Bcl-2 family proteins. Taken together these results provide a role of kaurane derivatives as apoptotic inducers in tumor cells. (C) 2009 Elsevier Ltd. All rights reserved.
• Biogenetic-like rearrangements of tetracyclic diterpenes
  作者：Robert M. Coates、Edward F. Bertram

  DOI：10.1021/jo00823a013

  日期：1971.12