2-(4-aminophenyl)-5,6,7-trimethoxy-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-aminophenyl)-5,6,7-trimethoxy-4H-chromen-4-one
• 英文别名: 4′-amino-5,6,7-trimethoxyflavone；4'-amino-5,6,7-trimethylbaicalein；4'-amino-5,6,7-trimethoxyflavone；2-(4-aminophenyl)-5,6,7-trimethoxychromen-4-one
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: LQPSNJXIAJVHLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-aminophenyl)-5,6,7-trimethoxy-4H-chromen-4-one 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(4-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)-methanesulfonamide
  参考文献：
  名称：

  Synthesis and Cytotoxic Effects of Sulfonamide-Substituted 5,6,7-Trimethoxyflavones on Human Cancer Cell Lines

  摘要：

  DOI：

  10.5012/bkcs.2013.34.8.2507
• 作为产物：
  描述：

  对硝基肉桂酸 在 氯化亚砜 、 三氟化硼乙醚 、 碘 、 tin(ll) chloride 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 、 苯 为溶剂， 生成 2-(4-aminophenyl)-5,6,7-trimethoxy-4H-chromen-4-one
  参考文献：
  名称：

  4′-Bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages

  摘要：

  The regulations of the NO and PGE(2) productions are research topics of interest in the field of anti-inflammatory drug development. In the present study, 5,6,7-trimethoxy- and 5,6,7-trihydroxyflavones 3a-3g were synthesized from cinnamic acid derivatives. In particular, 4'-bromo-5,6,7-trimethoxyflavone ( 3b) most potently inhibited the productions of NO and PGE(2) in LPS-treated RAW 264.7 cells ( IC(50) = 14.22 +/- 1.25 and 10.98 +/- 6.25 mu M, respectively), and these inhibitory effects were more potent than those of oroxylin A or baicalein. Consistent with these findings, 3b concentration-dependently reduced the LPS-induced expressions of iNOS and COX-2 at the protein and mRNA levels. In addition, the release of TNF-alpha, IL-6, and IL-1 beta and the mRNA expressions of these cytokines were reduced by 3b in a concentration-dependent manner. Furthermore, 3b attenuated the LPS-induced transcriptional activities of NF-kappa B and this was accompanied by parallel reductions in the degradation and phosphorylation of I kappa B-alpha, and consequently by a decrease in the nuclear translocation of the p65 subunit of NF-kappa B. Taken together, these results suggest that suppressions of the expressions of iNOS, COX-2, TNF-alpha, IL-6, and IL-1 beta via NF-kappa B inactivation are responsible for the anti-inflammatory effects of 3b. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.067

文献信息

• 一种合成6-羟基-2,3,4-三甲氧基-α-氯代苯乙酮的方法
  申请人：南华大学

  公开号：CN110498739A

  公开（公告）日：2019-11-26

  本发明公开了一种合成6‑羟基‑2,3,4‑三甲氧基‑α‑氯代苯乙酮的方法：以3,4,5‑三甲氧基苯酚为原料，以路易斯酸作为催化剂，以二氯甲烷作为反应溶剂，以氯乙酰氯作为酰化试剂，搅拌反应，反应完毕后，经后处理纯化，得到目标产物。本发明的方法能够较高收率地得到单酰基化产物，产物纯度高，避免了二取代副产物的生产；后处理方法简单，产物能够以固体形式析出，不需进行柱层析等操作，降低了操作步骤，节约了生产成本。
• Synthesis and Anticancer Activities of 5,6,7-Trimethylbaicalein Derivatives
  作者：Hua-Lin Liao、Ming-Kuan Hu

  DOI：10.1248/cpb.52.1162

  日期：——

  The aim of this study was to develop potential anticancer agents based on a naturally occurring baicalein, a flavonoid from Scatellariae radix. Cinnamic acid derivatives were converted to corresponding chlorides and then condensed with 3,4,5-trimethoxyphenol in the presence of BF3·Et2O to give chalcones. Intramolecular cyclization of these intermediates by the actions of DMSO/I2 afforded the desired trimethylbaicalein derivatives. Cell viability after treatment with the tested compound for 2 d was determined by a colorimetric MTT assay. The results indicated that most of the derivatives showed improved inhibition of proliferation of Hep G2 cells. Compound 9 was the most potent, in which the cell viability was reduced to <2% at the 25 μM level. In the case of Hep 3B cells, 8a, 8b and 8f showed moderate inhibition of their proliferation and 25 μM was required to reduce the viability to ca. 30%. On the other hand, prostate DU145 cells were more resistant. Most of the derivatives caused a 60% inhibition of DU145 cells only at a concentration of 100 μM or above.

  本研究旨在基于自然界中存在的黄芩素，一种来自黄芩根的黄酮类化合物，开发潜在的抗癌药物。通过将肉桂酸衍生物转化为相应的氯化物，然后在BF3·Et2O存在下与3,4,5-三甲氧基苯酚缩合，得到查尔酮。这些中间体在DMSO/I2的作用下发生分子内环化，得到所需的三甲氧基黄芩素衍生物。通过MTT比色法测定经测试化合物处理2天后的细胞活力。结果表明，大多数衍生物显示出对Hep G2细胞增殖抑制作用的提升。化合物9的抑制作用最强，其在25 μM浓度下细胞活力降至<2%。对于Hep 3B细胞，8a、8b和8f表现出中等程度的增殖抑制作用，需要25 μM浓度才能将活力降低至约30%。另一方面，前列腺DU145细胞的耐药性更强。大多数衍生物仅在100 μM或更高浓度下才导致DU145细胞60%的抑制率。
• Chromones and chromone derivatives and uses thereof
  申请人：Yen Mao-Hsiung

  公开号：US20060142211A1

  公开（公告）日：2006-06-29

  The present invention relates to chromones, novel chromone derivatives, and pharmaceutical formulations containing the same and methods of use thereof. Uses of the present invention include, but are not limited to, use for the prevention and treatment of septic shock, organ injury and other disorders. The compounds described herein can be salt forms and also water-soluble compounds.

  本发明涉及香豆素，新型香豆素衍生物，以及含有它们的制药配方和使用方法。本发明的用途包括但不限于预防和治疗败血性休克、器官损伤和其他疾病。所述化合物可以是盐形式和水溶性化合物。
• B环芳基脲黄酮类化合物、制造方法及其用途
  申请人：南华大学

  公开号：CN115160278A

  公开（公告）日：2022-10-11

  本发明公开了一类B环芳基脲黄酮类化合物、制造方法，及其在抗癌方面的作用。本发明将二芳基脲结构与黄酮相拼合，获得了一种新的具有较高生物活性的黄酮类化合物，拓宽了现有抗癌化合物的范围，可作为先导化合物继续优化。本发明具有良好的抗癌作用，满足医药领域的需要。
• DARC: Mapping Surface Topography by Ray-Casting for Effective Virtual Screening at Protein Interaction Sites
  作者：Ragul Gowthaman、Sven A. Miller、Steven Rogers、Jittasak Khowsathit、Lan Lan、Nan Bai、David K. Johnson、Chunjing Liu、Liang Xu、Asokan Anbanandam、Jeffrey Aubé、Anuradha Roy、John Karanicolas

  DOI：10.1021/acs.jmedchem.5b00150

  日期：2016.5.12

  Protein-protein interactions represent an exciting and challenging target class for therapeutic intervention using small molecules. Protein interaction sites are often devoid of the deep surface pockets presented by "traditional" drug targets, and crystal structures reveal that inhibitors typically engage these sites using very shallow binding modes. As a consequence, modern virtual screening tools developed to identify inhibitors of traditional drug targets do not perform as well when they are instead deployed at protein interaction sites. To address the need for novel inhibitors of important protein interactions, here we introduce an alternate docking strategy specifically designed for this regime. Our method, termed DARC (Docking Approach using Ray-Casting), matches the topography of a surface pocket "observed" from within the protein to the topography "observed" when viewing a potential ligand from the same vantage point. We applied DARC to carry out a virtual screen against the protein interaction site of human antiapoptotic protein Md-1 and found that four of the top-scoring 21 compounds showed clear inhibition in a biochemical assay. The K-i values for these compounds ranged from 1.2 to 21 mu M, and each had ligand efficiency comparable to promising small-molecule inhibitors of other protein protein interactions. These hit compounds do not resemble the natural (protein) binding partner of Mcl-1, nor do they resemble any known inhibitors of Md-1. Our results thus demonstrate the utility of DARC for identifying novel inhibitors of protein-protein interactions.