2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone | 199393-58-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone
• 英文别名: (E)-1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-enyl)phenyl]-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 199393-58-3
• 化学式: C₂₆H₃₂O₈
• 分子量: 472.535
• InChiKey: IIQUFYCTKZQFHH-UKTHLTGXSA-N

物化性质

• 沸点：
  630.9±55.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.33h， 生成 黄腐酚
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of Prenylated Chalcone Mannich Base Derivatives

  摘要：

  以氯代葡萄糖醇和适当的苯甲醛为起始原料，通过克莱森-施密特缩合反应、O-肾上腺素化反应和克莱森重排及脱保护反应，分别合成了前酰基查尔酮黄腐醇（1）和2′-羟基-3,4,4′-三甲氧基-6′-O-肾上腺素查尔酮（2）。根据预炔化查尔酮 1 或 2 与各种仲胺和甲醛在酸性醇溶剂中的曼尼希反应，合成了 10 种新型预炔化查尔酮曼尼希碱衍生物 3a-3e 和 4a-4e。此外，所有合成化合物都通过 MTT 法对四种人类癌细胞株（Aspc-1、SUN-5、HepG-2 和 HCT-116）进行了体外抗增殖活性评估。结果表明，大多数合成物对四种人类癌细胞具有中等至良好的抗增殖活性，IC50 值为 2.52 至 47.67 μM。

  DOI：

  10.1007/s10600-021-03380-4
• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 florisil 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 73.5h， 生成 2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of Prenylated Chalcone Mannich Base Derivatives

  摘要：

  以氯代葡萄糖醇和适当的苯甲醛为起始原料，通过克莱森-施密特缩合反应、O-肾上腺素化反应和克莱森重排及脱保护反应，分别合成了前酰基查尔酮黄腐醇（1）和2′-羟基-3,4,4′-三甲氧基-6′-O-肾上腺素查尔酮（2）。根据预炔化查尔酮 1 或 2 与各种仲胺和甲醛在酸性醇溶剂中的曼尼希反应，合成了 10 种新型预炔化查尔酮曼尼希碱衍生物 3a-3e 和 4a-4e。此外，所有合成化合物都通过 MTT 法对四种人类癌细胞株（Aspc-1、SUN-5、HepG-2 和 HCT-116）进行了体外抗增殖活性评估。结果表明，大多数合成物对四种人类癌细胞具有中等至良好的抗增殖活性，IC50 值为 2.52 至 47.67 μM。

  DOI：

  10.1007/s10600-021-03380-4

文献信息

• A Facile Synthesis of 6-C-Prenylflavanones
  作者：Xianyong Bu、Lianyun Zhao、Yulin Li

  DOI：10.1055/s-1997-1348

  日期：1997.11

  The first total synthesis of two natural 6-C-prenylflavanones, (±)-6-C-prenyleriodoctyol (1) and 6-C-prenylnaringenin (2), using the acetophenone derivative 6 as the key intermediate is described. This new efficient synthetic approach was mainly based on Claisen rearrangement and cyclization reaction.

  本文首次以苯乙酮衍生物 6 为关键中间体，全合成了两种天然 6-C-异戊烯基黄烷酮，即 (±)-6-C-prenyleriodoctyol (1) 和 6-C-异戊烯基柚皮素 (2)。这种新的高效合成方法主要基于克莱森重排和环化反应。
• Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity
  作者：Susanne Vogel、Susanne Ohmayer、Gabi Brunner、Jörg Heilmann

  DOI：10.1016/j.bmc.2008.02.079

  日期：2008.4

  A general strategy for the synthesis of 30-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2',3,4',5-tetrahydroxy-6'-methoxy-3'-prenylchalcone (9, IC50 3.2 +/- 0.4 mu M) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 +/- 0.5 mu M), were more active in comparison to 1 (IC50 9.4 +/- 1.4 mu M). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 +/- 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 +/- 2.1) showed that the prenyl side chain at C-3' has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4'-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 +/- 0.6, 3.8 +/- 0.4, and 3.8 +/- 0.5 Trolox equivalents, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and Antiproliferative Activity of Prenylated Chalcone Mannich Base Derivatives
  作者：Liang Su、Ke-Xiong Liu、Pei-Pei Han、Qiu-An Wang

  DOI：10.1007/s10600-021-03380-4

  日期：2021.5

  Prenylated chalcones xanthohumol (1) and 2′-hydroxy-3,4,4′-trimethoxy-6′-O-prenyl chalcone (2) were synthesized through the Claisen–Schmidt condensation, O-prenylation, and Claisen rearrangement and deprotection respectively, using phloroglucinol and appropriate benzaldehydes as starting materials. Based on the Mannich reaction of prenylated chalcone 1 or 2 with various secondary amines and formaldehyde in acid alcohol solvent, 10 novel prenylated chalcone Mannich base derivatives 3a–3e and 4a–4e were synthesized. Furthermore, all synthetic compounds were evaluated for antiproliferative activities in vitro against four human cancer cell lines (Aspc-1, SUN-5, HepG-2, and HCT-116) by MTT assay. The results showed that most of them exhibit moderate to good antiproliferative activities against the four human cancer cells with IC50 values of 2.52 to 47.67 μM.

  以氯代葡萄糖醇和适当的苯甲醛为起始原料，通过克莱森-施密特缩合反应、O-肾上腺素化反应和克莱森重排及脱保护反应，分别合成了前酰基查尔酮黄腐醇（1）和2′-羟基-3,4,4′-三甲氧基-6′-O-肾上腺素查尔酮（2）。根据预炔化查尔酮 1 或 2 与各种仲胺和甲醛在酸性醇溶剂中的曼尼希反应，合成了 10 种新型预炔化查尔酮曼尼希碱衍生物 3a-3e 和 4a-4e。此外，所有合成化合物都通过 MTT 法对四种人类癌细胞株（Aspc-1、SUN-5、HepG-2 和 HCT-116）进行了体外抗增殖活性评估。结果表明，大多数合成物对四种人类癌细胞具有中等至良好的抗增殖活性，IC50 值为 2.52 至 47.67 μM。