6,7-dimethoxy-3-(4-methylphenyl)-2H-2-chromenone | 949580-53-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6,7-dimethoxy-3-(4-methylphenyl)-2H-2-chromenone
• 英文别名: 6,7-dimethoxy-3-p-tolylchromen-2-one；6,7-Dimethoxy-3-(4-methylphenyl)chromen-2-one
• CAS: 949580-53-4
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: YXMQCEQWMVWKII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-3-(4-methylphenyl)-2H-2-chromenone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 以100%的产率得到3-[4-(bromomethyl)phenyl]-6,7-dimethoxy-2H-2-chromenone
  参考文献：
  名称：

  Extensive SAR and Computational Studies of 3-{4-[(Benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) Derivatives

  摘要：

  AP2238 was the first compound published to bind both anionic sites of the human acetylcholinesterase, allowing the simultaneous inhibition of the catalytic and the amyloid-beta pro-aggregating activities of AChE. Here we attempted to derive a comprehensive structure-activity relationship picture for this molecule, affording 28 derivatives for which AChE and BChE inhibitory activities were evaluated. Selected compounds were also tested for their ability to prevent the AChE-induced A beta-aggregation. Moreover, docking simulations and molecular orbital calculations were performed.

  DOI：

  10.1021/jm070100g
• 作为产物：
  描述：

  2,4,5-三甲氧基苯甲醛 在 乙酸酐 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 生成 6,7-dimethoxy-3-(4-methylphenyl)-2H-2-chromenone
  参考文献：
  名称：

  3-(4-{[Benzyl(methyl)amino]methyl}phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) Inhibits Both Acetylcholinesterase and Acetylcholinesterase-Induced β-Amyloid Aggregation:  A Dual Function Lead for Alzheimer's Disease Therapy

  摘要：

  In recent years, the investigation of acetylcholinesterase (AChE) inhibitors has gained further interest, because the involvement of the peripheral site of the enzyme in the beta-amyloid (Abeta) aggregation process has been disclosed. We present here, for the first time, a direct evidence of the Abeta antiaggregating action of an AChE inhibitor (AP2238) purposely designed to bind at both the catalytic and the peripheral sites of the human enzyme.

  DOI：

  10.1021/jm0340602

文献信息

• Scoparone chemical modification into semi-synthetic analogues featuring 3-substitution for their anti-inflammatory activity
  作者：Chetan Kumar、Pankaj Chibber、Ritu Painuli、Syed Assim Haq、Ram A. Vishwakarma、Gurdarshan Singh、Naresh K. Satti、Ravindra S. Phatake

  DOI：10.1007/s11030-023-10687-7

  日期：——

  investigation, we reported the synthesis of nineteen semi-synthetic 3-substituted scoparone analogues, followed by their characterization using analytical methods such as NMR, HPLC, and HRMS. All compounds screened for in vitro and in vivo study for their ability to reduce inflammation. The SAR study worked effectively for this particular scoparone 3-substitution, as compounds 3, 4, 9, 16, 18, and 20 displayed

  天然产物 （NPs） 继续作为开发新生物活性分子的结构模型，并改进新药的识别过程。香豆素是 NP 中研究最多的化合物之一，目前正在彻底研究其生物学效应。在本研究中，我们报道了 19 种半合成 3-取代东伞酮类似物的合成，然后使用 NMR、HPLC 和 HRMS 等分析方法对其进行表征。所有化合物都经过体外和体内研究筛选，以确定其减轻炎症的能力。SAR 研究对这种特定的 Scoparone 3-取代有效，因为化合物 3、4、9、16、18 和 20 对 TNF-α 的体外结果优于母体分子。同样，化合物 3 和 17 显示出更高的 IL-6 抑制百分比。化合物 3、4 和 12 也被体内研究确定为有前途的候选化合物，其抑制百分比高于母体 Scoparone 分子。从所有体外和体内研究中可以明显看出，化合物 3 显示出最有效的抗炎活性。