zonarone | 39707-56-7

• 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: zonarone
• 英文别名: 2-[[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]cyclohexa-2,5-diene-1,4-dione
• CAS: 39707-56-7
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: ZRLCSLPEEURTPE-QFUCXCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  zonarone 在 sodium dithionite 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 37.75h， 生成 (8R,S)-8,12-epoxyzonarol dibenzyl ether
  参考文献：
  名称：

  Total synthesis of yahazunol, zonarone and isozonarone

  摘要：

  The synthesis of the marine natural products zonarone and isozonarone was achieved via (+)-albicanic acid, a sesquiterpene of the drimane type. Coupling of the appropiate drimane-synthon with lithiated hydroquinone ethers led to sesquiterpene arenes, which were further modified to the target molecules. Stereoselective epoxidation followed by regioselective opening of the oxirane ring yielded yahazunol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00346-0
• 作为产物：
  描述：

  (1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl-methanol 在 吡啶-2,6-二羧酸 n-氧化物 、 ammonium cerium(IV) nitrate 、 仲丁基锂 、 lithium 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 、 氨 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.83h， 生成 zonarone
  参考文献：
  名称：

  Total synthesis of yahazunol, zonarone and isozonarone

  摘要：

  The synthesis of the marine natural products zonarone and isozonarone was achieved via (+)-albicanic acid, a sesquiterpene of the drimane type. Coupling of the appropiate drimane-synthon with lithiated hydroquinone ethers led to sesquiterpene arenes, which were further modified to the target molecules. Stereoselective epoxidation followed by regioselective opening of the oxirane ring yielded yahazunol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00346-0

文献信息

• Total synthesis of the marine sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone
  作者：Jörg Schröder、Christine Magg、Karlheinz Seifert

  DOI：10.1016/s0040-4039(00)00891-1

  日期：2000.7

  The total synthesis of the naturally occurring sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone was achieved starting from β-ionone, which was transformed via (+)-albicanic acid to (+)-albicanal and (−)-drim-7-en-11-al. Coupling of the aldehydes with lithiated hydroquinone ethers and further modification of the coupling products led to the target

  天然倍半萜烯对苯二酚唑纳洛尔和异唑烷酮以及倍半萜烯醌佐那隆和异唑烷酮的全合成是从β-紫罗兰酮开始的，β-紫罗兰酮通过（+）-白蚁酸转化为（+）-白三醛和（-）-drim- 7-en-11-al。醛与锂化对苯二酚醚的偶联以及偶联产物的进一步修饰产生了目标分子。
• Structure-activity relationship of anti-inflammatory meroterpenoids isolated from <i>Dictyopteris polypodioides</i> in RAW264 cells
  作者：Momochika Kumagai、Akana Matsuda、Nozomi Shiiba、Tomoki Tsuruta、Hikaru Endo、Keisuke Nishikawa、Yoshiki Morimoto

  DOI：10.1093/bbb/zbae038

  日期：——

  In this study, we explored anti-inflammatory compounds from the brown alga Dictyopteris polypodioides and isolated 7 meroterpenoids. Their anti-inflammatory activities were evaluated using the lipopolysaccharide-stimulated mouse macrophage cell line, RAW264. Yahazunol (1) exhibited similar nitric oxide (NO) production inhibitory activity as zonarol (2), which has previously been shown to be an anti-inflammatory

  在这项研究中，我们从褐藻 Dictyopteris polypodioides 中探索了抗炎化合物，并分离出了 7 种类萜。使用脂多糖刺激的小鼠巨噬细胞系 RAW264 评估它们的抗炎活性。 Yahazunol (1) 表现出与 zonarol (2) 相似的一氧化氮 (NO) 产生抑制活性，zonarol (2) 此前已被证明是一种抗炎化合物。 Yahazunol (1)、zonarol (2) 和 isozonarol (3) 不仅抑制 RAW264 细胞中 NO 的产生，还抑制诱导型一氧化氮合酶、白细胞介素 6 和 CC 基序趋化因子配体 2 mRNA 表达。 11 种化合物（包括其合成类似物）的构效关系揭示了对苯二酚部分在这些倍半萜类化合物在 RAW264 细胞中的抗炎活性中的重要性。由于细胞内脱乙酰化作用，二乙酰化 zonarol (9) 表现出与 zonarol 相当的活性。这
• Total synthesis of bioactive drimane–epoxyquinol hybrid natural products: macrophorin A, 4′-oxomacrophorin A, and 1′-epi-craterellin A
  作者：Sumanta Garai、Goverdhan Mehta

  DOI：10.1016/j.tetlet.2014.09.075

  日期：2014.11

  Total synthesis of novel hybrid natural products, merosesquiterpenoids macrophorin A, 4'-oxomacrophorin A, and l'-epi-craterellin A has been accomplished following a general strategy based on a sacrificial Diels-Alder-retroDiels-Alder approach to control regio- and stereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and Absolute Configuration of Zonarol. A Fungitoxic Hydroquinone from the Brown Seaweed Dictyoptfris Zonarioides(1)
  作者：Kenji Mori、Makoto Komatsu

  DOI：10.1002/bscb.19860950906

  日期：——

  AbstractA total synthesis of both the enantiomers of zonarol 1 was accomplished. Measurements of the ORD‐CD spectra of two bicyclic intermediates coupled with direct comparison of the natural and synthetic zonarol 1 established the absolute configuration of the naturally occurring (+)‐zonarol 1 as 1R, 4aR, 8aR.
• Stereoselective total syntheses of the fungitoxic hydroquinones (.+-.)-zonarol and (.+-.)-isozonarol
  作者：Steven C. Welch、A. S. C. Prakasa Rao

  DOI：10.1021/jo00404a023

  日期：1978.5