arzanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: arzanol
• 英文别名: 3-[[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methylpyran-2-one
• 化学式: C₂₂H₂₆O₇
• 分子量: 402.444
• InChiKey: ZOIAPLVBZQQHCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  arzanol 、 三甲基硅烷化重氮甲烷 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到methylarzanol
  参考文献：
  名称：

  Arzanol, an Anti-inflammatory and Anti-HIV-1 Phloroglucinol α-Pyrone from Helichrysum italicum ssp. microphyllum

  摘要：

  An acetone extract of Helichrysum italicum ssp. microphyllum afforded the phloroglucinol alpha-pyrone arzanol (1a) as a potent NF-kappa B inhibitor. Arzanol is identical with homoarenol (2a), whose structure should be revised. The phloroglucinol-type structure of arzanol and the 1,2,4-trihydroxyphenyl-type structure of the base-induced fragmentation product of homoarenol could be reconciled in light of a retro-Fries-type fragmentation that triggers a change of the hydroxylation pattern of the aromatic moiety. On the basis of these findings, the structure of arenol, the major constituent of the clinically useful antibiotic arenarin, should be revised from 2b to 1b, solving a long-standing puzzle over its biogenetic derivation. An alpha-pyrone (micropyrone, 7), the monoterpene rac-E-omega-oleoyloxylinalol (10), four known tremetones (9a-d), and the dimeric pyrone helipyrone (8) were also obtained. Arzanol inhibited HIV-1 replication in T cells and the release of pro-inflammatory cytokines in LPS-stimulated primary monocytes, qualifying as a novel plant-derived anti-inflammatory and antiviral chemotype worth further investigation.

  DOI：

  10.1021/np060581r
• 作为产物：
  描述：

  丙酸乙酯 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 PPA 、 氯仿 、 mineral oil 为溶剂， 反应 17.84h， 生成 arzanol
  参考文献：
  名称：

  亚烷基异二聚体的多组分 Carba-Betti 策略 - Arzanol 的全合成和构效关系

  摘要：

  使用异二聚体间苯二酚吡喃酮 arzanol 的合成作为基准反应，已经开发了 Betti 多组分反应的 carba 版本。利用酚类成分的氟活化和亚胺离子作为二价和“传递性”醛等价物的使用，该反应已被用于殖民一个生物学上特权但以前无法进入的化学空间区域，并研究 arzanol 的结构 - 活性关系针对一系列促炎靶点（mPGES-1、5-LO）。

  DOI：

  10.1002/ejoc.201101193

文献信息

• A Multicomponent Carba-Betti Strategy to Alkylidene Heterodimers - Total Synthesis and Structure-Activity Relationships of Arzanol
  作者：Alberto Minassi、Lavinia Cicione、Andreas Koeberle、Julia Bauer、Stefan Laufer、Oliver Werz、Giovanni Appendino

  DOI：10.1002/ejoc.201101193

  日期：2012.2

  Using the synthesis of the heterodimeric phloroglucinyl pyrone arzanol as a benchmark reaction, a carba-version of the Betti multicomponent reaction has been developed. Capitalizing on the fluorous activation of the phenolic component and the use of iminium ions as bivalent and "transmissive" aldehyde equivalents, the reaction has been used to colonize a biologically privileged but previously inaccessible

  使用异二聚体间苯二酚吡喃酮 arzanol 的合成作为基准反应，已经开发了 Betti 多组分反应的 carba 版本。利用酚类成分的氟活化和亚胺离子作为二价和“传递性”醛等价物的使用，该反应已被用于殖民一个生物学上特权但以前无法进入的化学空间区域，并研究 arzanol 的结构 - 活性关系针对一系列促炎靶点（mPGES-1、5-LO）。
• Arzanol, an Anti-inflammatory and Anti-HIV-1 Phloroglucinol α-Pyrone from <i>Helichrysum </i><i>italicum</i> ssp. <i>microphyllum</i>
  作者：Giovanni Appendino、Michela Ottino、Nieves Marquez、Federica Bianchi、Anna Giana、Mauro Ballero、Olov Sterner、Bernd L. Fiebich、Eduardo Munoz

  DOI：10.1021/np060581r

  日期：2007.4.1

  An acetone extract of Helichrysum italicum ssp. microphyllum afforded the phloroglucinol alpha-pyrone arzanol (1a) as a potent NF-kappa B inhibitor. Arzanol is identical with homoarenol (2a), whose structure should be revised. The phloroglucinol-type structure of arzanol and the 1,2,4-trihydroxyphenyl-type structure of the base-induced fragmentation product of homoarenol could be reconciled in light of a retro-Fries-type fragmentation that triggers a change of the hydroxylation pattern of the aromatic moiety. On the basis of these findings, the structure of arenol, the major constituent of the clinically useful antibiotic arenarin, should be revised from 2b to 1b, solving a long-standing puzzle over its biogenetic derivation. An alpha-pyrone (micropyrone, 7), the monoterpene rac-E-omega-oleoyloxylinalol (10), four known tremetones (9a-d), and the dimeric pyrone helipyrone (8) were also obtained. Arzanol inhibited HIV-1 replication in T cells and the release of pro-inflammatory cytokines in LPS-stimulated primary monocytes, qualifying as a novel plant-derived anti-inflammatory and antiviral chemotype worth further investigation.