2-hydroxy-3-bromo-4,6-dimethoxyacetophenone | 18064-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3-bromo-4,6-dimethoxyacetophenone
• 英文别名: 1-(3-Bromo-2-hydroxy-4,6-dimethoxyphenyl)ethan-1-one；1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone
• CAS: 18064-89-6
• 化学式: C₁₀H₁₁BrO₄
• 分子量: 275.099
• InChiKey: ONBWYQYLBKAJTM-UHFFFAOYSA-N

物化性质

• 熔点：
  188–189°C
• 沸点：
  375.8±42.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-bromo-4,6-dimethoxyacetophenone 在 四(三苯基膦)钯 、 碘 、 caesium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.25h， 生成 5,7-dimethoxy-2-(4-methoxy-phenyl)-8-phenyl-chromen-4-one
  参考文献：
  名称：

  The first synthesis of podocarflavone A and its analogs and evaluation of their antimycobacterial potential against Mycobacterium tuberculosis with the support of virtual screening

  摘要：

  DOI：

  10.1080/14786419.2021.1893317
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 在 potassium bromate 、 氢溴酸 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 2-hydroxy-3-bromo-4,6-dimethoxyacetophenone
  参考文献：
  名称：

  藤黄5'-溴-2'-羟基-4,4',6'-三甲氧基查尔酮及其异构体3'-溴-2'-羟基-4,4',6-'三甲氧基查尔酮的合成

  摘要：

  天然存在的 5'-溴-2'-羟基-4,4',6'-三甲氧基查尔酮 1（Garcinia nervosa 的成分）及其位置异构体 3'-bromo-2'-hydroxy-4 的明确合成，描述了 4',6'-三甲氧基查耳酮 6。

  DOI：

  10.3184/030823410x12754665381128

文献信息

• Antifungal Activity and Studies on Mode of Action of Novel Xanthoxyline-Derived Chalcones
  作者：Paula Boeck、Paulo C. Leal、Rosendo A. Yunes、Valdir Cechinel Filho、Silvia López、Maximiliano Sortino、Andrea Escalante、Ricardo L. E. Furlán、Susana Zacchino

  DOI：10.1002/ardp.200400929

  日期：2005.3

  substituent on ring A are sufficient for these compounds to have antifungal properties. The chalcone 3‐(2‐chlorophenyl)‐1‐(2′‐hydroxy‐4′,6′‐dimethoxyphenyl)prop‐2‐en‐1‐one, with a Cl atom in the ortho position of benzene ring B showed the best antifungal activity against standardized strains of Trichophyton rubrum (MIC = 12.5 μg/mL) and inhibited all of the ten clinical isolates of T. rubrum tested (MIC at which

  查耳酮和查耳酮类化合物，其中大多数是新化合物，通过适当的醛和黄嘌呤的碱催化缩合制备，通过琼脂稀释法测试了对一组酵母、hialohyphomycetes 和皮肤癣菌的抗真菌特性。结果表明，仅存在“类黄酮素”取代模式或环 A 上的 2'-OH 取代都不足以使这些化合物具有抗真菌特性。查耳酮 3-(2-氯苯基)-1-(2'-羟基-4', 6'-二甲氧基苯基)丙-2-烯-1-1，在苯环B的邻位有一个Cl原子表明对红色毛癣菌标准化菌株 (MIC = 12.5 μg/mL) 具有最佳抗真菌活性，并抑制所有十种临床分离株。rubrum 测试（50% [MIC50] 和 90% [MIC90] 的分离株被抑制时的 MIC = 12.5 和 25 μg/mL）。关于其作用方式，粗糙脉孢菌试验显示该查耳酮产生的抑制晕圈出现斑点，强烈表明它可以通过抑制真菌细胞壁发挥作用。该查尔酮似乎是一种菌丝畸形诱导剂，因为在
• Synthesis, Biological Evaluation and In Silico Study of β-Chloro Vinyl Chalcones as Inhibitors of the TNF-α, IL-6 With Anticancer and Antioxidant Activity
  作者：Babasaheb P. Bandgar、Baliram S. Hote、Shivraj H Nile

  DOI：10.2174/157018011796576051

  日期：2011.10.1

  A series of novel β-chloro vinyl chalcones have been synthesized from substituted (Z) – 3 – chloro – 3- phenylacraldehydes with 1-(3 – bromo – 2 – hydroxyl-4,6- dimethoxyphenyl)ethanone by Claisen-Schmidt condensation reaction. Compounds were screened for anti-inflammatory, anticancer and antioxidant activity. Compounds 6a, 6d and 6f revealed promising anti-inflammatory activity (87 – 99 %) with less cytotoxicity (4 – 9 %) at 10 µ M. Compounds 6a, 6d, 6e and 6f having significant anticancer activity (71 – 83 %). Bioavailability of compounds were checked by in vitro cytotoxicity and confirmed to be nontoxic. Structure activity relationship and in silico drug relevant properties of compounds revealed as potential candidates for future drug discovery study.

  通过克莱森-施密特缩合反应，从取代的 (Z) - 3 - 氯 - 3 - 苯基乙醛与 1-(3-溴 - 2 - 羟基-4,6-二甲氧基苯基)乙酮合成了一系列新型 β-氯乙烯基查耳酮。对化合物进行了抗炎、抗癌和抗氧化活性筛选。化合物 6a、6d 和 6f 显示出良好的抗炎活性（87 - 99 %）和较低的细胞毒性（4 - 9 %）（10 µ M），化合物 6a、6d、6e 和 6f 具有显著的抗癌活性（71 - 83 %）。通过体外细胞毒性检测了化合物的生物利用度，证实其无毒。化合物的结构活性关系和与药物相关的硅学特性表明，它们是未来药物发现研究的潜在候选化合物。
• Chalcone dihalides—II
  作者：D.J. Donnelly、J.A. Donnelly、E.M. Philbin

  DOI：10.1016/0040-4020(72)80054-1

  日期：1972.1

  2,3-Dibromo-2′-hydroxy-3-(2-thienyl)propiophenones, with base, gave mixtures of the corresponding chromone and coumaranone and were readily converted into their 3-alkoxyl derivatives. Chromones were obtained by pyrolysing the dibromides and coumaranones by treatment of the 3-alkoxyl derivatives with aqueous ethanolic alkali.

  具有碱的2，3-二溴-2′-羟基-3-（2-噻吩基）苯乙酮给出了相应的色酮和香豆酮的混合物，并很容易地转化成它们的3-烷氧基衍生物。通过用含水乙醇碱处理3-烷氧基衍生物，将二溴化物和香豆酮酮热解，从而获得苯并二氢吡喃酮。
• Hydroxychalcones induce apoptosis in B16-F10 melanoma cells via GSH and ATP depletion
  作者：Andréia Lilian Formento Navarini、Louise Domeneghini Chiaradia、Alessandra Mascarello、Márcio Fritzen、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.ejmech.2008.09.009

  日期：2009.4

  Searching for leading compounds of new drugs for cancer therapy, we studied the toxicity of 13 hydroxychalcones never tested before toward melanoma cell line (B16-F10). The compounds were obtained by aldolic condensation between aldehydes and hydroxylated acetophenones, in alkaline conditions. Three of them showed cytotoxicity to the cell line. Two of them induced mitochondrial GSH and ATP depletion and promoted cell death through apoptosis in melanoma cells. One of the compounds induced cell death through necrosis but did not significantly decrease the intracellular mitochondrial GSH and ATP levels in melanoma cells. The results suggest that the predominant factor for the activity is the molecule shape, and secondarily the number of hydroxyl groups. (c) 2008 Published by Elsevier Masson SAS.
• Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi
  作者：Deise M. Borchhardt、Alessandra Mascarello、Louise Domeneghini Chiaradia、Ricardo J. Nunes、Glaucius Oliva、Rosendo A. Yunes、Adriano D. Andricopulo

  DOI：10.1590/s0103-50532010000100021

  日期：——

  Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 mu M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.