1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]ethanone | 30403-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]ethanone
• 英文别名: 2,4-Dihydroxy-6-methoxy-3-prenylacetophenone；2,4-dihydroxy-3-prenyl-6-methoxyacetophenone；preremirol；2,4-Dihydroxy-6-methoxy-3-<3-methyl-buten-(2)-yl-(1)>-acetophenon；3-(γ,γ-Dimethyl-allyl)-phloracetophenon-6-methylether；2-O-Methyl-5-C-prenyl-phloroacetophenone
• CAS: 30403-01-1
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: KASLWEHUDINBOP-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C
• 沸点：
  403.5±35.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]ethanone 在 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 苯 为溶剂， 反应 40.5h， 生成 glychalcone A
  参考文献：
  名称：

  FIRST TOTAL SYNTHESIS OF (±)-GLYFLAVANONE-A

  摘要：

  First convergent synthesis ()-glyflavanone-A (1), a novel pyranoflavanone natural product, starting from phloroacetophenone and p-anisaldehyde is described.

  DOI：

  10.1081/scc-120003156
• 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 盐酸 、 水 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 94.0h， 生成 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]ethanone
  参考文献：
  名称：

  作为潜在抗肿瘤剂的新型异戊二烯化查耳酮衍生物的设计、合成和生物评价

  摘要：

  设计并合成了一系列具有广谱抗癌潜力的新型异戊二烯化查耳酮衍生物。一些合成的目标化合物对 LNCaP（前列腺癌细胞系）、K562（人白血病细胞）、A549（人肺癌细胞系）和 HeLa（宫颈癌细胞系）细胞系表现出有效的抗增殖活性。在活性化合物中，( E )-1-(4-(2-(二乙基氨基)乙氧基)-2-羟基-6-甲氧基-3-(3-甲基丁-2-烯-1-基)苯基)- 3-(pyridin-3-yl)prop-2-en-1-one ( C36 ) 直接与蛋白激酶 B (PKB)（又称 AKT）相互作用，显着抑制 pPI3K、pAKT(Ser473) 蛋白水平，从而抑制通过诱导细胞凋亡、阻止细胞周期来抑制癌细胞的生长。我们的研究为异戊二烯化查耳酮衍生物作为潜在 AKT 抑制剂在癌症治疗中的潜在应用提供了支持。

  DOI：

  10.1016/j.ejps.2023.106660

文献信息

• Total Synthesis and in Vitro Anti-Tumor-Promoting Activities of Racemic Acetophenone Monomers from <i>Acronychia trifoliolata</i>
  作者：Chihiro Morita、Yukiko Kobayashi、Yohei Saito、Katsunori Miyake、Harukuni Tokuda、Nobutaka Suzuki、Eiichiro Ichiishi、Kuo-Hsiung Lee、Kyoko Nakagawa-Goto

  DOI：10.1021/acs.jnatprod.6b00646

  日期：2016.11.23

  through 1,3- or 3,3-sigmatropic rearrangement. The synthesized racemic compounds were evaluated in an anti-tumor-promoting assay using the Epstein–Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. All tested compounds significantly inhibited EBV-EA activation. Especially, racemic acronyculatin I (1) displayed the most potent inhibitory effects

  六苯乙酮衍生物，acronyculatins我（1），J（2），K（3），L（4），N（5）和O（6），最近从Acronychia trifoliolata，和已知的acronyculatin的结构中分离出来。B（7）被修改。由于分离产品的数量有限，以及它们的结构相似性，所以外消旋的肩甲素I–L，N，O和B（1 – 7合成）以确认其结构并获得足够的材料用于生物学评估。通过羟基保护，烯丙基化或烯丙基化，环氧化和环化的各种顺序，将三羟基苯乙酮转化为目标化合物。Ç -Prenylations通过直接加入异戊烯基或通过1,3-或3,3-σ重排进行。通过在Raji细胞中由12 - O-十四烷酰phorbol-13-乙酸酯诱导的爱泼斯坦-巴尔病毒早期抗原（EBV-EA）活化，在抗肿瘤促进试验中评估了合成的外消旋化合物。所有测试的化合物均显着抑制EBV-EA活化。尤其是外消旋顶体素I（1）显示出最有效的抑制作用，IC
• 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, Cytotoxicity, and Antioxidative Activity of Minor Prenylated Chalcones from <i>Humulus lupulus</i>
  作者：Susanne Vogel、Jörg Heilmann

  DOI：10.1021/np800188b

  日期：2008.7.1

  The minor hop (Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1 '',2 ''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconar-. ingenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC50 values comparable to xanthohumol (8.2-19.2 mu M). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.
• Orth,W.A.; Riedl,W., Justus Liebigs Annalen der Chemie, 1963, vol. 663, p. 74 - 82
  作者：Orth,W.A.、Riedl,W.

  DOI：——

  日期：——
• Ahluwalia, V. K.; Sharma, N. D.; Mittal, Bina, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 238 - 241
  作者：Ahluwalia, V. K.、Sharma, N. D.、Mittal, Bina、Gupta, S. R.

  DOI：——

  日期：——