4-(((4-fluorophenyl)imino)methyl)benzene-1,3-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(((4-fluorophenyl)imino)methyl)benzene-1,3-diol
• 英文别名: 4-[(4-Fluorophenyl)iminomethyl]benzene-1,3-diol
• 化学式: C₁₃H₁₀FNO₂
• 分子量: 231.226
• InChiKey: BUAFEGWQPALQRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  柠康酸 、 4-(((4-fluorophenyl)imino)methyl)benzene-1,3-diol 以 neat (no solvent, solid phase) 为溶剂， 生成
  参考文献：
  名称：

  使用共晶工程方法对N-水杨基苯胺衍生物光致变色性质的新见解

  摘要：

  在这项贡献中，我们旨在使用晶体工程方法来修改茴香的光致变色特性。先前的工作表明共结晶可改变指甲的光致变色行为。在这里，用21种共形成物（羧酸，酰胺和卤代苯衍生物）对15种茴香衍生物（包括8种新描述的茴香）进行了全面筛选，得到了89种新的茴香共结晶。大量的结果允许对复杂的光致变色机理进行统计上有效的洞察，从而提供连续现象的证据，而不是经典的二元光致变色/非光致变色现象。该贡献中发现的“弱光致变色化合物”的发现为这一点提供了支持。所有结果都证实了烯醇-亚胺是必要条件，减少涉及目标部分的短接点数量是微调特性的有趣方法，因为它既影响电子又影响结构。根据这种“连续假设”，已经对二面角的作用进行了探索，并显示其与光致变色的强度有关，而不是决定其发生的原因。此外，在这一贡献中，我们提出了一种解释DRS（漫反射光谱）数据的新颖方法。已经探究了二面角的作用，并表明它与光致变色的强度有关，而不是决定其发生的原

  DOI：

  10.1021/acs.cgd.9b00363
• 作为产物：
  描述：

  (2,4-dihydroxy-benzylidene)-dimethyl-ammonium; dichloro phosphate 以 乙醇 、 水 为溶剂， 反应 5.5h， 生成 4-(((4-fluorophenyl)imino)methyl)benzene-1,3-diol
  参考文献：
  名称：

  2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead

  摘要：

  Hsp90 is a molecular chaperone that heals diverse array of biomolecules ranging from multiple oncogenic proteins to the ones responsible for development of resistance to chemotherapeutic agents. Moreover they are over-expressed in cancer cells as a complex with co-chaperones and under-expressed in normal cells as a single free entity. Hence inhibitors of Hsp90 will be more effective and selective in destroying cancer cells with minimum chances of acquiring resistance to them. In continuation of our goal to rationally develop effective small molecule azomethines against Hsp90, we designed few more compounds belonging to the class of 2,4-dihydroxy benzaldehyde derived imines (1-13) with our validated docking protocol. The molecules exhibiting good docking score were synthesized and their structures were confirmed by IR, H-1 NMR and mass spectral analysis. Subsequently, they were evaluated for their potential to suppress Hsp90 ATPase activity by Malachite green assay. The antiproliferative effect of the molecules were examined on PC3 prostate cancer cell lines by adopting 3-(4,5-dimethythiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay methodology. Finally, schiff base 13 emerged as the lead molecule for future design and development of Hsp90 inhibitors as anticancer agents. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.02.003

文献信息

• 2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead
  作者：Sayan Dutta Gupta、B. Revathi、Gisela I. Mazaira、Mario D. Galigniana、C.V.S. Subrahmanyam、N.L. Gowrishankar、N.M. Raghavendra

  DOI：10.1016/j.bioorg.2015.02.003

  日期：2015.4

  Hsp90 is a molecular chaperone that heals diverse array of biomolecules ranging from multiple oncogenic proteins to the ones responsible for development of resistance to chemotherapeutic agents. Moreover they are over-expressed in cancer cells as a complex with co-chaperones and under-expressed in normal cells as a single free entity. Hence inhibitors of Hsp90 will be more effective and selective in destroying cancer cells with minimum chances of acquiring resistance to them. In continuation of our goal to rationally develop effective small molecule azomethines against Hsp90, we designed few more compounds belonging to the class of 2,4-dihydroxy benzaldehyde derived imines (1-13) with our validated docking protocol. The molecules exhibiting good docking score were synthesized and their structures were confirmed by IR, H-1 NMR and mass spectral analysis. Subsequently, they were evaluated for their potential to suppress Hsp90 ATPase activity by Malachite green assay. The antiproliferative effect of the molecules were examined on PC3 prostate cancer cell lines by adopting 3-(4,5-dimethythiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay methodology. Finally, schiff base 13 emerged as the lead molecule for future design and development of Hsp90 inhibitors as anticancer agents. (C) 2015 Elsevier Inc. All rights reserved.
• New Insights into Photochromic Properties of <i>N</i>-Salicylideneaniline Derivatives Using a Cocrystal Engineering Approach
  作者：Gabriel M. Mercier、Koen Robeyns、Nikolay Tumanov、Benoit Champagne、Johan Wouters、Tom Leyssens

  DOI：10.1021/acs.cgd.9b00363

  日期：2019.10.2

  we aim to modify the photochromic properties of anils using a crystal engineering approach. Previous work has shown cocrystallization to alter the photochromic behavior of anils. Here, a full screening of 15 anil derivatives (including 8 newly described anils) with 21 coformers (carboxylic acids, amides, and halogenated benzene derivatives) was performed, resulting in 89 new anil cocrystals. This

  在这项贡献中，我们旨在使用晶体工程方法来修改茴香的光致变色特性。先前的工作表明共结晶可改变指甲的光致变色行为。在这里，用21种共形成物（羧酸，酰胺和卤代苯衍生物）对15种茴香衍生物（包括8种新描述的茴香）进行了全面筛选，得到了89种新的茴香共结晶。大量的结果允许对复杂的光致变色机理进行统计上有效的洞察，从而提供连续现象的证据，而不是经典的二元光致变色/非光致变色现象。该贡献中发现的“弱光致变色化合物”的发现为这一点提供了支持。所有结果都证实了烯醇-亚胺是必要条件，减少涉及目标部分的短接点数量是微调特性的有趣方法，因为它既影响电子又影响结构。根据这种“连续假设”，已经对二面角的作用进行了探索，并显示其与光致变色的强度有关，而不是决定其发生的原因。此外，在这一贡献中，我们提出了一种解释DRS（漫反射光谱）数据的新颖方法。已经探究了二面角的作用，并表明它与光致变色的强度有关，而不是决定其发生的原