2'-hydroxy-4,4',6'-trimethoxydihydrochalcone | 3791-75-1

• 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'-hydroxy-4,4',6'-trimethoxydihydrochalcone
• 英文别名: 1-(2-hydroxy-4,6-dimethoxy-phenyl)-3-(4-methoxy-phenyl)propan-1-one；1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-propan-1-one；hydroxy-2' trimethoxy-4',6',4 dihydrochalcone；2'-Hydroxy-4',6',4-trimethoxydihydrochalcone；2'-hydroxy-4,4',6'-trimethoxydihydrochalkone；flavokawain A；Flavokawin A；1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one
• CAS: 3791-75-1
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: KGFYDIZALLKOLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-4,4',6'-trimethoxydihydrochalcone 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 5,7-dimethoxy-3-(4-methoxybenzyl)chroman-4-one
  参考文献：
  名称：

  New Convenient Synthesis of Homoisoflavanones and (±)‐Di‐O‐methyldihydroeucomin

  摘要：

  Upon reaction of 1-(2-hydroxyphenyl)-3-phenylpropane-1-ones (2'-hydroxydihydrochalcones) with dimethylaminodimethoxymethane in boiling toluene, the corresponding 3-benzylchromones are obtained in excellent yields. These latter lead to 3-benzylchroman-4-ones (bomoisoflavanones) by catalytic hydrogenetion. These reactions were applied to the synthesis of (+/-)-3-benzylchroman-4-one and (+/-)-3(4-methoxybenzyl)-5,7-dimethoxychroman-4-one, (+/-)-di-O-methyldihydroeucomin.

  DOI：

  10.1081/scc-200049789
• 作为产物：
  描述：

  夫拉美诺 以 甲醇 、 乙醚 为溶剂， 生成 2'-hydroxy-4,4',6'-trimethoxydihydrochalcone
  参考文献：
  名称：

  Nilsson,M., Acta Chemica Scandinavica (1947), 1961, vol. 15, p. 154 - 158

  摘要：

  DOI：

文献信息

• [EN] COMPOUNDS, THEIR SYNTHESES, AND THEIR USES<br/>[FR] COMPOSÉS, LEUR SYNTHÈSE ET LEURS UTILISATIONS
  申请人：UNIV LOUISVILLE RES FOUND

  公开号：WO2010019861A1

  公开（公告）日：2010-02-18

  Embodiments of the present invention provide compounds (such as Formula (I) compounds, Formula (II) compounds, and various embodiments thereof). Compositions comprising those compounds are also provided. Methods for their preparation are included. Also, uses of the compounds are included, such as administering and treating diseases (e.g., cancer and infections).

  本发明实施例提供化合物（如式（I）化合物、式（II）化合物及其各种实施例）。还提供包含这些化合物的组合物。包括它们的制备方法。此外，还包括化合物的用途，如给药和治疗疾病（例如癌症和感染）。
• Synthesis, Cytotoxicity, and Anti-<i>Trypanosoma cruzi</i> Activity of New Chalcones
  作者：José C. Aponte、Manuela Verástegui、Edith Málaga、Mirko Zimic、Miguel Quiliano、Abraham J. Vaisberg、Robert H. Gilman、Gerald B. Hammond

  DOI：10.1021/jm800812k

  日期：2008.10.9

  Synthesis of a cytotoxic dihydrochalcone, first isolated from a traditional Amazonian medicinal plant Iryanthera juruensis Warb (Myristicaceae), followed by a comprehensive SAR analysis of saturated and unsaturated chalcone synthetic intermediates, led to the identification of analogues with selective and significant in vitro anti- Trypanosoma cruzi activity. Further SAR studies were undertaken with

  合成具有细胞毒性的二氢查耳酮，首先从传统的亚马逊药用植物鸢尾菊中提取（Myristicaceae），然后对饱和和不饱和查耳酮合成中间体进行全面的SAR分析，从而鉴定出具有选择性和显着体外抗锥虫病的类似物。克鲁兹活动。通过合成21个含有两个烯丙氧基部分的新查耳酮进行了进一步的SAR研究，结果发现了2'，4'-二烯丙氧基-6'-甲氧基查耳酮，在浓度低于25 microM时对这种寄生虫具有更高的选择性，其中四个表现出大于12的选择性指数。
• Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalcones <i>via</i> palladium(<scp>ii</scp>)-catalyzed oxidative cyclization
  作者：Seung Hwan Son、Yang Yil Cho、Hyung-Seok Yoo、Soo Jin Lee、Young Min Kim、Hyu Jeong Jang、Dong Hwan Kim、Jeong-Won Shin、Nam-Jung Kim

  DOI：10.1039/d1ra01672e

  日期：——

  Divergent and versatile synthetic routes to flavones and flavanones via efficient Pd(II) catalysis are disclosed. These Pd(II) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives, via discriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic

  公开了通过有效的 Pd( II ) 催化合成黄酮和黄烷酮的不同且通用的合成路线。根据氧化剂和添加剂，这些 Pd( II ) 催化剂分别以高度原子经济的方式通过涉及脱氢的区分氧化环化序列，方便地从 2'-羟基二氢查耳酮中提供各种黄酮和黄烷酮作为常见的中间体。
• Anti-ulcer agent comprising chalcone derivative as effective ingredient
  申请人：Tsumura & Co.

  公开号：US05106871A1

  公开（公告）日：1992-04-21

  The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: ##STR1## wherein X and Y independently stand for a hydrogen atom or together form a single bond, R.sub.1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R.sub.2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R.sub.3 stands for hydroxyl group or a methoxy group, R.sub.4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R.sub.5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R.sub.6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R.sub.7 stands for a hydrogen atom or a methoxy group.

  本发明涉及一种抗溃疡剂，其包括以下一般式I所代表的化合物作为有效成分，以及包含在由该一般式I所代表的化合物中的一种新的查尔酮衍生物：##STR1## 其中X和Y独立地代表氢原子或共同形成一个单键，R.sub.1代表羟基、乙酰氧基、羧甲氧基或甲氧羰基甲氧基，R.sub.2代表氢原子、异戊二烯基、异戊基或丙基，R.sub.3代表羟基或甲氧基，R.sub.4代表氢原子、羟基或甲氧基，R.sub.5代表氢原子、羟基、甲氧基或异戊基，R.sub.6代表羟基、甲氧基或羧甲氧基，R.sub.7代表氢原子或甲氧基。
• Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives
  作者：Li Wang、Zheng-Wei Li、Wei Zhang、Rui Xu、Fei Gao、Yang-Feng Liu、Ya-Jun Li

  DOI：10.3390/molecules191016447

  日期：——

  A one-step synthesis of phloretin derivatives 2–11 from phloretin in good to excellent yields is reported. Their structures were characterized by 1H-NMR, 13C-NMR and MS, and the structures of 8 and 11 were determined by X-ray diffraction analysis. A mechanism for the formation of 9–11 is proposed. Compared with the anticancer drug docetaxel, phloretin, phloretin derivatives and phlorizin exhibited

  报道了从根皮素一步合成根皮素衍生物 2-11 的方法，收率很好。它们的结构通过1H-NMR、13C-NMR和MS表征，8和11的结构通过X射线衍射分析确定。提出了形成 9-11 的机制。与抗癌药物多西紫杉醇相比，根皮素、根皮素衍生物和根皮苷对 MDA-MB-231、SPC-A1、A549、MCF-7 和 EC109 细胞系表现出中等的细胞毒性。在所有测试的化合物中，7 种对五种细胞系表现出最强的细胞毒性，并且在 MDA-MB-231 细胞中比多西他赛更有活性。我们的研究结果表明，这些衍生物作为抗癌剂的进一步开发具有广阔的前景。