1-(2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)ethan-1-one | 77179-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)ethan-1-one
• 英文别名: 4-O-methyl-3-(3-methyl-2-butenyl) phloroacetophenone；2,6-dihydroxy-4-methoxy-3-C-prenylacetophenone；4-O-methyl-3-prenylphloroacetophenone；acronyculatin S；1-(3-isoprenyl-2,6-dihydroxy-4-methoxyphenyl)ethan-1-one；2,6-dihydroxy-4-methoxy-5-C-prenylacetophenone；1-[2,6-Dihydroxy-4-methoxy-3-(3-methylbut-2-enyl)phenyl]ethanone
• CAS: 77179-30-7
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: WELTVQLQYUWYIT-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±45.0 °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-(2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)ethan-1-one 以 氯仿 、 甲苯 为溶剂， 反应 4.25h， 生成 mallotojaponin C
  参考文献：
  名称：

  Mallotojaponins B和C：全合成，抗寄生虫评估和SAR初步研究

  摘要：

  已经实现了首个总皂角苷B和C以及几种类似物的合成。还已经对合成的化合物针对恶性疟原虫和布鲁氏锥虫进行了生物学评估。

  DOI：

  10.1021/acs.orglett.5b03676
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 28.33h， 生成 1-(2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)ethan-1-one
  参考文献：
  名称：

  一种天然产物Xanthohumol D及其衍生物的合成方法及用途

  摘要：

  本发明公布了天然产物Xanthohumol D（I）及其类似物（II）的合成方法及用途，其结构式如下：得到的新型异戊烯基查尔酮类化合物，其中Xanthohumol D对枯草芽孢杆菌有较好的抑制活性。本发明制备路线工艺步骤较少，原料易得，适合工业化生产。

  公开号：

  CN110590520A

文献信息

• 一种天然产物Xanthohumol D及其衍生物的合成方法及用途
  申请人：山东理工大学

  公开号：CN110590520A

  公开（公告）日：2019-12-20

  本发明公布了天然产物Xanthohumol D（I）及其类似物（II）的合成方法及用途，其结构式如下：得到的新型异戊烯基查尔酮类化合物，其中Xanthohumol D对枯草芽孢杆菌有较好的抑制活性。本发明制备路线工艺步骤较少，原料易得，适合工业化生产。
• Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds
  作者：Alexander L. Eaton、Seema Dalal、M. Belen Cassera、Shuqi Zhao、David G. I. Kingston

  DOI：10.1021/acs.jnatprod.6b00347

  日期：2016.6.24

  antiplasmodial and cytocidal activities against the malaria parasite Plasmodium falciparum, was synthesized in three steps from 2′,4′,6′-trihydroxyacetophenone, and various derivatives were synthesized in an attempt to improve the bioactivity of this class of compounds. Two derivatives, the simple prenylated phloroglucinols 12 and 13, were found to have comparable antiplasmodial activities to that of mallotojaponin

  我们从前证明了来自Mallotus oppositifolius的间苯三酚Mallotojaponin C（1），由2'，4'，6'-三羟基苯乙酮和三个不同步骤合成了对疟原虫恶性疟原虫具有抗疟原虫和杀细胞活性。为了改善这类化合物的生物活性，合成了衍生物。发现两种衍生物，即简单的烯丙基化的间苯三酚12和13，具有与马洛托皂苷C相当的抗血浆活性。
• 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.
• Balani, S. K.; Gupta, R. K.; Krishnamurti, M., Journal of the Indian Chemical Society, 1980, vol. 57, # 12, p. 1238 - 1239
  作者：Balani, S. K.、Gupta, R. K.、Krishnamurti, M.

  DOI：——

  日期：——
• Hossain, M. Amzad; Salehuddin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 11, p. 2399 - 2401
  作者：Hossain, M. Amzad、Salehuddin

  DOI：——

  日期：——