4-((benzylimino)methyl)benzene-1,3-diol | 215232-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-((benzylimino)methyl)benzene-1,3-diol
• 英文别名: 4-(Benzyliminomethyl)benzene-1,3-diol
• CAS: 215232-61-4
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: SDIFBXJNIHGYTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((benzylimino)methyl)benzene-1,3-diol 、 dimethylgallium,hydrate 以 四氢呋喃 为溶剂， 以86%的产率得到κ(2)-N,O-benzyliminomethylbenzene-1,3-diolatodimethylgallium
  参考文献：
  名称：

  四配位二甲基镓化合物的水解稳定性各不相同

  摘要：

  通过氢氧化二甲基镓与双齿路易斯碱反应制备四配位的二甲基镓配合物，并评估其在水中分解的稳定性，这是确定其作为放射性药物（尤其是针对特定受体蛋白的药物）潜在用途的关键特性。由配体和氢氧化二甲基镓制备了六种结构类型的模型化合物，其中含有带有氧-氧，氧-氮和硫-氮供体原子的双齿配体。它们通过光谱学表征，在两种情况下通过X射线晶体学表征。稳定的百分比解络（CH 3）2镓+时在丙酮暴露于1000当量的水从路易斯碱部d通过1 H NMR测定的图6用作每种化合物的相对水解稳定性的量度。在我们研究的化合物中，在这些条件下的水解百分比为10％至100％，最水解稳定的化合物被证明是基于N-烷基水杨基醛二酸酯供体的那些。

  DOI：

  10.1021/om980413x
• 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-((benzylimino)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.
• Four-Coordinate Dimethylgallium Compounds Vary in Stability toward Hydrolysis
  作者：Robert W. Chesnut、Richard R. Cesati、Cathy S. Cutler、Sara L. Pluth、John A. Katzenellenbogen

  DOI：10.1021/om980413x

  日期：1998.10.1

  oxygen−oxygen, oxygen−nitrogen, and sulfur−nitrogen donor atoms, were prepared from the ligand and dimethylgallium hydroxide; they were characterized spectroscopically and, in two cases, by X-ray crystallography. The percentage decomplexation of the stable (CH3)2Ga+ unit from the Lewis base when exposed to 1000 equiv of water in acetone-d6, determined by 1H NMR, was used as a measure of the relative hydrolytic

  通过氢氧化二甲基镓与双齿路易斯碱反应制备四配位的二甲基镓配合物，并评估其在水中分解的稳定性，这是确定其作为放射性药物（尤其是针对特定受体蛋白的药物）潜在用途的关键特性。由配体和氢氧化二甲基镓制备了六种结构类型的模型化合物，其中含有带有氧-氧，氧-氮和硫-氮供体原子的双齿配体。它们通过光谱学表征，在两种情况下通过X射线晶体学表征。稳定的百分比解络（CH 3）2镓+时在丙酮暴露于1000当量的水从路易斯碱部d通过1 H NMR测定的图6用作每种化合物的相对水解稳定性的量度。在我们研究的化合物中，在这些条件下的水解百分比为10％至100％，最水解稳定的化合物被证明是基于N-烷基水杨基醛二酸酯供体的那些。