3-geranyl-1-(2'-methylpropanoyl)phloroglucinol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-geranyl-1-(2'-methylpropanoyl)phloroglucinol
• 英文别名: (E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylpropan-1-one；2-Geranyl-4-isobutyrylphloroglucinol；1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4,6-trihydroxyphenyl]-2-methylpropan-1-one
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: TXDNBNXWWCEVMG-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-geranyl-1-(2'-methylpropanoyl)phloroglucinol 在 4-二甲氨基吡啶 、 碳酸氢钠 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-((3-(2-(3,3-dimethyloxiran-2-yl)ethyl)-3-methyloxiran-2-yl)methyl)-4-isobutyrylbenzene-1,3,5-triyl triacetate
  参考文献：
  名称：

  (-)-Japonicol C的对映特异性全合成

  摘要：

  (±)-japonicol B和(-)-japonicol C的高效且收敛的首次全合成已经完成。合成路线的显着点是路易斯酸催化的弗里德尔-克拉夫茨反应，形成一锅 C-C 和 C-O 键，导致三环类萜骨架的构建，一锅 Pd(OH) 2 /C 催化异构化/氢化和位点选择性sp 3 C-H氧化。

  DOI：

  10.1021/acs.orglett.1c00560
• 作为产物：
  描述：

  间苯三酚 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 3-geranyl-1-(2'-methylpropanoyl)phloroglucinol
  参考文献：
  名称：

  作为有效的LOX抑制剂的天然化合物2,4,6-三羟基-3-香叶基苯乙酮（tHGA）的命中优化：合成，结构-活性关系（SAR）研究和计算分配。

  摘要：

  合成了一系列新的2,4,6-三羟基-3-香叶基-苯乙酮（tHGA）类似物，并评估了它们对脂氧合酶（LOX）的抑制活性。由于疏水相互作用的减少，异戊酸酯化的类似物4a⁻g（半数最大抑制浓度（IC50）值在35μM至95μM之间）没有表现出比tHGA（3a）更好的抑制活性（IC50值：23.6μM）当烷基链长度减少时。与tHGA（3a）相比，一种具有IC50值为15.3μM的香叶基化类似物3d表现出更好的LOX抑制活性，这与我们之前的发现是一致的。动力学研究表明，活性最高的类似物（3e）和tHGA（3a）充当竞争性抑制剂。分子对接和分子动力学模拟的计算机模拟方法的结合表明，这些类似物的亲脂性进一步增强了LOX抑制活性。根据吸收，分布，代谢，排泄和毒性（ADMET）以及通过komputer辅助技术（TOPKAT）进行的毒性预测，所有geranylated类似物（3a⁻g）均无肝毒性作用且可生物降

  DOI：

  10.3390/molecules23102509

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Synthesis of Natural Acylphloroglucinol-Based Antifungal Compounds against <i>Cryptococcus</i> Species
  作者：Qian Yu、Ranga Rao Ravu、Melissa R. Jacob、Shabana I. Khan、Ameeta K. Agarwal、Bo-Yang Yu、Xing-Cong Li

  DOI：10.1021/acs.jnatprod.6b00224

  日期：2016.9.23

  synthesized to identify antifungal compounds against Cryptococcus spp. that cause the life-threatening disseminated cryptococcosis. In vitro antifungal testing showed that 17 compounds were active against C. neoformans ATCC 90113, C. neoformans H99, and C. gattii ATCC 32609, with minimum inhibitory concentrations (MICs) in the range 1.0–16.7 μg/mL. Analysis of the structure and antifungal activity of these

  合成了33种基于天然产物的酰基间苯三酚衍生物，以鉴定针对隐球菌的抗真菌化合物。导致威胁生命的散发性隐球菌病。体外抗真菌测试表明，17种化合物对活性隐球菌ATCC 90113，隐球菌H99，和隐球菌ATCC 32609，用范围为1.0-16.7μg/ mL的最低抑菌浓度（MIC）。对这些化合物的结构和抗真菌活性的分析表明，2，4-二酰基-和2-酰基-4-烷基间苯二酚比O-烷基-酰基间苯二酚具有更高的活性。发现的最有希望的化合物是2-甲基-1-（2,4,6-三羟基-3-（4-异丙基苄基）苯基）丙-1-酮（11j），对哺乳动物的Vero和LLC-PK1细胞系表现出有效的抗真菌活性（MICs，1.5-2.1μg/ mL）和低细胞毒性（IC 50值> 50μg/ mL）。该化合物可用作进一步合成具有改善的抗真菌活性的新类似物的模板。当前工作的发现可能会有助于将来的抗真菌发现，从而为隐球菌病新疗法的药物开发提供帮助。
• Synthesis and Docking Studies of 2,4,6-Trihydroxy-3-Geranylacetophenone Analogs as Potential Lipoxygenase Inhibitor
  作者：Chean Ng、Kamal Rullah、Mohd Aluwi、Faridah Abas、Kok Lam、Intan Ismail、Radhakrishnan Narayanaswamy、Fadzureena Jamaludin、Khozirah Shaari

  DOI：10.3390/molecules190811645

  日期：——

  acids, such as linoleic acid to form hydroperoxides. The search for selective LOX inhibitors may provide new therapeutic approach for inflammatory diseases. Herein, we report the synthesis of tHGA analogs using simple Friedel-Craft acylation and alkylation reactions with the aim of obtaining a better insight into the structure-activity relationships of the compounds. All the synthesized analogs showed potent

  从药用植物 Melicope ptelefolia 中分离出的天然产物分子 2,4,6-trihydroxy-3-geranyl-acetophenone (tHGA) 显示出有效的脂氧合酶 (LOX) 抑制活性。众所周知，LOX 在炎症反应中起着重要作用，因为它催化不饱和脂肪酸（如亚油酸）氧化形成氢过氧化物。寻找选择性LOX抑制剂可能为炎症性疾病提供新的治疗方法。在此，我们报告了使用简单的 Friedel-Craft 酰化和烷基化反应合成 tHGA 类似物，目的是更好地了解化合物的构效关系。所有合成的类似物均以剂量依赖性方式显示出有效的大豆 15-LOX 抑制活性（IC50 = 10.31-27。61 μM)，其中化合物 3e 的活性是 tHGA 的两倍。然后应用分子对接来揭示化合物 3e 在大豆 15-LOX 结合位点中的重要结合相互作用。研究结果表明，较长的带有脂族链 (5Cs) 和芳族基团的酰基的存在会显着影响酶活性。
• Synthesis of natural-like acylphloroglucinols with anti-proliferative, anti-oxidative and tube-formation inhibitory activity
  作者：Qiu Sun、Sebastian Schmidt、Martina Tremmel、Jörg Heilmann、Burkhard König

  DOI：10.1016/j.ejmech.2014.08.017

  日期：2014.10

  Two series of natural and natural-like mono- and bicyclic acylphloroglucinols derived from secondary metabolites in the genus Hypericum (Hypericaceae) were synthesised and tested in vitro for anti-proliferative and tube-formation inhibitory activity in human microvascular endothelial cells (HMEC-1). In addition, their anti-oxidative activity was determined via an ORAC-assay. The first series of compounds (4a-e) consisted of geranylated monocyclic acylphloroglucinols with varying aliphatic acyl substitution patterns, which were subsequently cyclised to the corresponding 2-methyl-2-prenylchromane derivatives (5a and 5d). The second series involved compounds containing a 2,2-dimethylchromane skeleton with differing aromatic acyl substitution (6a-d and 7a-e). Compound 7a, (5,7-dihydroxy-2,2-dimethylchroman-6-yl)-(3,4-dihydroxyphenyl)methanone), showed the highest in vitro anti-proliferative activity with an IC50 of 0.88 +/- 0.08 mu M and a remarkable anti-oxidative activity of 2.8 +/- 0.1 TE from the ORAC test. Interestingly, the high anti-proliferative activity of these acylphloroglucinols was not associated with tube-formation inhibition. Compounds (E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylbutan-1-one (4d) and (5,7-dihydroxy-2,2-dimethylchroman-6-yl)(3,4-dimethoxyphenyl)methanone (6a) exhibited moderate to weak anti-proliferative effects (IC50 11.0 +/- 1 mu M and 48.0 +/- 43 mu M, respectively) and inhibited the capillary-like tube formation of HMEC-1 in vitro, whereas 7a was inactive. The most active compound in the ORAC assay was 7c, which exhibited an anti-oxidative effect of 6.6 +/- 1.0 TE. However, this compound showed only weak activity during the proliferation assay (IC50 53.8 +/- 0.3) and did not inhibit tube-formation. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Efficient synthesis of polycycles bearing prenylated, geranylated, and farnesylated citrans: application to 3′-prenylrubranine and petiolin D regioisomer
  作者：Xue Wang、Yong Rok Lee

  DOI：10.1016/j.tet.2011.09.075

  日期：2011.11

  Efficient synthetic routes for biologically interesting polycycles with prenylated, geranylated, and farnesylated citrans were developed from several trihydroxybenzenes with prenyl, geranyl, and farnesyl groups on the benzene rings. Ethylenediamine diacetate-catalyzed cyclization by a domino aldol-type/electrocyclization/H-shift/hetero Diels-Alder reaction of prenylated, geranylated, and farnesylated trihydroxybenzenes with citral or trans,trans-farnesal provided a variety of tetracycles bearing prenylated, geranylated, and farnesylated citrans. The mechanistic pathway for regio- and stereochemistry of synthesized polycycles was described. As an application of this methodology, 3'-prenylrubranine and petiolin D regioisomer were first synthesized. (C) 2011 Elsevier Ltd. All rights reserved.