plicatin B acetate | 151071-02-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: plicatin B acetate
• 英文别名: methyl (E)-3-[4-acetyloxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoate
• CAS: 151071-02-2
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: SVLSQZFHERPDFC-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  plicatin B acetate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以74%的产率得到drupanin
  参考文献：
  名称：

  Artepillin C isoprenomics: Design and synthesis of artepillin C isoprene analogues as lipid peroxidation inhibitor having low mitochondrial toxicity

  摘要：

  We designed and synthesized isoprene analogues of artepillin C, a major component of Brazilian propolis, and investigated the inhibitory activity on lipid peroxidation of rat liver mitochondria (RLM) and RLM toxicity based on isoprenomics. We succeeded in the synthesis of artepillin C isoprene analogues using regioselective prenylation within the range from 22% to 53% total yield. Reactivity of artepillin C and its isoprene analogues with ABTS (2,2'-Azinobis(3-ethylbenzothiazoline-6-sulfonate)) radical cations showed only a slight difference among the molecules. The isoprene side-chain elongation analogues of artepillin C showed almost the same inhibitory activity against RLM lipid peroxidation as artepillin C. Artepillin C and its isoprene analogues had very weak RLM uncoupling activity. Moreover, artepillin C and its isoprene analogues exhibited a lower inhibitory activity against adenosine 5'-triphosphate (ATP) synthesis by about two orders of magnitude than the effective inhibitory activity against RLM lipid peroxidation. From these results we conclude that artepillin C isoprene analogues could be potent lipid peroxidation inhibitors having low mitochondrial toxicity. We also conclude that elongation of the isoprene side chain of artepillin C to increase lipophilicity had little influence on the inhibitory activity toward RLM lipid peroxidation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.015
• 作为产物：
  描述：

  4-溴-2-(3-甲基丁-2-烯基)苯酚 在 palladium diacetate 4-二甲氨基吡啶 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 plicatin B acetate
  参考文献：
  名称：

  The synthesis of Plicatin B via the Heck reaction

  摘要：

  The anti-microbial natural product Plicatin B has been synthesized in 53% overall yield using a Heck reaction as the key step. The optimum conditions for this reaction have been determined. Halophenols proved much less reactive than their corresponding acetates.

  DOI：

  10.1016/s0040-4039(00)73632-x

文献信息

• Diterpene glycosides and other constituents from argentinian baccharis species
  作者：C. Zdero、F. Bohlmann、R.M. King、H. Robinson

  DOI：10.1016/s0031-9422(00)83754-1

  日期：1986.1

  investigation of the aerial parts of nine Baccharis species from Argentina gave 37 new compounds, seven ent -clerodanes, 13 ent -labdanes, two friedolabdanes, a nor-labdane ketone, seven coumaric acid derivatives, two umbelliferone derivatives, a flavanone, three sesquiterpenes including a nor-furanocadinene and a propiophenone derivative. Ten of the diterpenes were glycosides. The structures and the configurations

  摘要 对阿根廷 9 种 Baccharis 地上部分的研究得到了 37 个新化合物，7 个 ent-clerodanes，13 个 ent-labdanes，2 个 Friedolabdanes，一个nor-labdane 酮，7 个香豆酸衍生物，2 个伞形酮衍生物，1 个黄烷酮，3 个倍半萜烯包括去甲呋喃卡二烯和苯丙酮衍生物。十种二萜是糖苷。结构和构型由高场核磁共振光谱和一些化学转化确定。二萜的绝对构型是根据观察到的棉花效应提出的，在一种情况下，通过使用霍罗方法和 1 H NMR 确定获得的主要苯基丁酸酯的构型。讨论了化学分类。
• Synthesis of phenolic natural products using palladium catalyzed coupling reactions
  作者：Roderick W. Bates、Christine J. Gabel、Jianhua Ji、Thota Rama-Devi

  DOI：10.1016/0040-4020(95)00441-a

  日期：1995.7

  Derivatives of 2,4-diiodophenol are shown to undergo palladium catalyzed carbonylation and alkyne coupling reactions in excellent to moderate yield and high regioselectivity. The scope of these reactions is explored. Palladium catalyzed reactions are employed as the key steps in the synthesis of three phenolic natural products: Plicatin B, Drupanin and Eutypine.
• The synthesis of Plicatin B via the Heck reaction
  作者：Roderick W Bates、Christine J Gabel

  DOI：10.1016/s0040-4039(00)73632-x

  日期：1993.5

  The anti-microbial natural product Plicatin B has been synthesized in 53% overall yield using a Heck reaction as the key step. The optimum conditions for this reaction have been determined. Halophenols proved much less reactive than their corresponding acetates.
• Artepillin C isoprenomics: Design and synthesis of artepillin C isoprene analogues as lipid peroxidation inhibitor having low mitochondrial toxicity
  作者：Yoshihiro Uto、Shutaro Ae、Daisuke Koyama、Mitsutoshi Sakakibara、Naoki Otomo、Mamoru Otsuki、Hideko Nagasawa、Kenneth L. Kirk、Hitoshi Hori

  DOI：10.1016/j.bmc.2006.04.015

  日期：2006.8

  We designed and synthesized isoprene analogues of artepillin C, a major component of Brazilian propolis, and investigated the inhibitory activity on lipid peroxidation of rat liver mitochondria (RLM) and RLM toxicity based on isoprenomics. We succeeded in the synthesis of artepillin C isoprene analogues using regioselective prenylation within the range from 22% to 53% total yield. Reactivity of artepillin C and its isoprene analogues with ABTS (2,2'-Azinobis(3-ethylbenzothiazoline-6-sulfonate)) radical cations showed only a slight difference among the molecules. The isoprene side-chain elongation analogues of artepillin C showed almost the same inhibitory activity against RLM lipid peroxidation as artepillin C. Artepillin C and its isoprene analogues had very weak RLM uncoupling activity. Moreover, artepillin C and its isoprene analogues exhibited a lower inhibitory activity against adenosine 5'-triphosphate (ATP) synthesis by about two orders of magnitude than the effective inhibitory activity against RLM lipid peroxidation. From these results we conclude that artepillin C isoprene analogues could be potent lipid peroxidation inhibitors having low mitochondrial toxicity. We also conclude that elongation of the isoprene side chain of artepillin C to increase lipophilicity had little influence on the inhibitory activity toward RLM lipid peroxidation. (c) 2006 Elsevier Ltd. All rights reserved.