2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)-N-(p-tolyl)acetamide | 892563-31-4

• 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-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)-N-(p-tolyl)acetamide
• 英文别名: 2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxy-N-(4-methylphenyl)acetamide
• CAS: 892563-31-4
• 化学式: C₂₄H₁₉NO₅
• 分子量: 401.419
• InChiKey: BZAZLSXXIKKUJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  白杨素 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.17h， 生成 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)-N-(p-tolyl)acetamide
  参考文献：
  名称：

  Structure-based design of flavone-based inhibitors of wild-type and T315I mutant of ABL

  摘要：

  The existence of drug resistance caused by mutations in the break-point cluster region-Abelson (BCR-ABL) tyrosine kinase domain remains a clinical challenge due to limited treatment options for effective CML therapies. Here, we report a series of flavone-based common inhibitors equipotent for the wild type and the most drug-resistant T315I mutant of BCR-ABL. The original hit 1 was extensively modified through a structure-based drug design strategy, especially by varying the C7 acetamide appendage of the scaffold to exploit extended interactions with P-loop residues. Structural features relevant to the stabilization of the newly identified inhibitors in the ATP-binding site of ABL are discussed in detail. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.095

文献信息

• Synthesis of new chrysin derivatives with substantial antibiofilm activity
  作者：Sukhen Bhowmik、Pragya Anand、Riyanki Das、Tirtharaj Sen、Yusuf Akhter、Manash C. Das、Utpal C. De

  DOI：10.1007/s11030-020-10162-7

  日期：2022.2

  causing a very low efficacy. Very few chrysin derivatives possessing antimicrobial activity with a low anti-biofilm efficacy have been found in the literature. Thus, it has been attempted to synthesize a series of new chrysin derivatives (CDs). In this study, twenty-two new derivatives have been synthesized via its 7-OH modulation and antibiofilm activity was evaluated against a model bacterium viz.

  摘要 微生物对常规抗菌药物的多药耐药机制是当今面临的一个共同的健康问题。因此，寻找和开发新型抗菌药物处于生物化学的前沿领域。通过分子建模和虚拟筛选对各种天然产物进行功能化或合成化合物是获得潜在线索的方法。白杨素是植物次生代谢产物之一，普遍存在于大多数植物中。然而，它具有多维潜力，具有非常低的生物利用度，导致非常低的功效。在文献中很少发现具有抗生物膜功效的抗微生物活性的白杨素衍生物。因此，已尝试合成一系列新的白杨素衍生物（CDs）。在这项研究中，. 大肠杆菌MTCC 40（革兰氏阴性）。已发现与白杨素（CD 的前体）相比，编码为2a、2b、2c、2e、2f、2g、2h、2i、3j、3k和3l的 11 种 CD 对浮游形式的大肠杆菌更有效。生物膜抑制研究表明，与白杨素 (33.57%) 相比， 2a (93.57%)、2b (92.14%)、2f (92.14%) 和3l (93.57%)的结
• Structure-based design of flavone-based inhibitors of wild-type and T315I mutant of ABL
  作者：Hyeonjeong Choe、Jieun Kim、Sungwoo Hong

  DOI：10.1016/j.bmcl.2013.05.095

  日期：2013.8

  The existence of drug resistance caused by mutations in the break-point cluster region-Abelson (BCR-ABL) tyrosine kinase domain remains a clinical challenge due to limited treatment options for effective CML therapies. Here, we report a series of flavone-based common inhibitors equipotent for the wild type and the most drug-resistant T315I mutant of BCR-ABL. The original hit 1 was extensively modified through a structure-based drug design strategy, especially by varying the C7 acetamide appendage of the scaffold to exploit extended interactions with P-loop residues. Structural features relevant to the stabilization of the newly identified inhibitors in the ATP-binding site of ABL are discussed in detail. (C) 2013 Elsevier Ltd. All rights reserved.