4-hydroxy-2'-hydroxysalicylanil | 1761-59-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-2'-hydroxysalicylanil
• 英文别名: 4-(((2-hydroxyphenyl)imino)methyl)benzene-1,3-diol；Resorcyliden-2-amino-phenol；2-(2,4-Dihydroxy-benzylidenamino)-phenol；Benzene-1,3-diol, 4-(2-hydroxyphenyliminomethyl)-；4-[(2-hydroxyphenyl)iminomethyl]benzene-1,3-diol
• CAS: 1761-59-7
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: VISLUSLXCVLVTQ-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(hydride)(chloride)(carbonyl)(triphenylarsine)3] 、 4-hydroxy-2'-hydroxysalicylanil 以 甲醇 、 苯 为溶剂， 反应 12.0h， 以63%的产率得到
  参考文献：
  名称：

  Synthesis, spectral, dna binding and cleavage properties of ruthenium(II) Schiff base complexes containing PPh3/AsPh3 as co-ligands

  摘要：

  一种二羟基苯甲醛希夫碱配体（L1-L3）及其钌(II) 配合物的元素分析、1H、13C、31P NMR、质谱、UV 分析、1H、13C、31P NMR、质谱、紫外-可见光谱和红外光谱。与 钌（II）络合物的结合情况进行了研究。 光谱进行了研究。实验表明，所有化合物都能通过静电模式和本征模式与 DNA 结合。 通过静电模式与 DNA 结合。 在类似的实验条件下估算出了本征结合常数（Kb）。吸收光谱 吸收光谱研究表明，钌（II）配合物的本征结合常数在 1.6-6.5 之间。 范围为 1.6-8.6 X 104 M-1。其中[Ru(CO)(PPh3)2(L3) 的结合力比其他复合物更强。此外，对所有 裂解特性进行了测试。

  DOI：

  10.2298/jsc121201073s
• 作为产物：
  描述：

  间苯二酚 在 三氯氧磷 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 10.5h， 生成 4-hydroxy-2'-hydroxysalicylanil
  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

• Dodwad, S.S.; Patil, Indira; Datar, M.G., Journal of the Indian Chemical Society, 1984, vol. 61, p. 595 - 597
  作者：Dodwad, S.S.、Patil, Indira、Datar, M.G.

  DOI：——

  日期：——
• OH-substituted tridentate ONO Schiff base ligands and related molybdenum(VI) complexes for solvent-free (ep)oxidation catalysis with TBHP as oxidant
  作者：Weili Wang、Jean-Claude Daran、Rinaldo Poli、Dominique Agustin

  DOI：10.1016/j.molcata.2016.02.021

  日期：2016.5

  Molybdenum complexes with ONO tridentate Schiff base ligands based on salicylideneaminophenolato (SAP) backbone with OH substitution on the salicyl arene ring have been synthesized and characterized. The molecular structures of the full series of OH substituted molybdenum complexes were determined by X-ray crystallography as monomers stabilized by one solvent molecule, [MoO2L(D)]. All dimeric complexes [MoO2L](2) were tested for the epoxidation of cyclooctene and cyclohexene under organic solvent-free conditions using aqueous TBHP as oxidant. The position of the OH on the SAP-modified ligand influenced the catalytic activity of the respective complexes. DFT calculations for the catalytic cycle yield energy spans in agreement with the experimentally observed activity trend. (C) 2016 Elsevier B.V. All rights reserved.
• In vitro and in vivo anti-inflammatory properties of imine resveratrol analogues
  作者：Danielle Cristina Zimmermann-Franco、Bruna Esteves、Leticia Moroni Lacerda、Isabela de Oliveira Souza、Juliana Alves dos Santos、Nícolas de Castro Campos Pinto、Elita Scio、Adilson David da Silva、Gilson Costa Macedo

  DOI：10.1016/j.bmc.2018.08.029

  日期：2018.9

  Resveratrol is a natural polyphenol found mainly on red grapes and in red wine, pointed as an important antiinflammatory/immunomodulatory molecule. However, its bioavailability problems have limited its use encouraging the search for new alternatives agents. Thus, in this study, we synthesize 12 resveratrol analogues (6 imines, 1 thioimine and 5 hydrazones) and investigated its cytotoxicity, antioxidant activity and in vitro antiinflammatory/immunomodulatory properties. The most promising compounds were also evaluated in vivo. The results showed that imines presented less cytotoxicity, were more effective than resveratrol on DPPH scavenger and exhibited an anti-inflammatory profile. Among them, the imines with a radical in the para position, on the ring B, not engaged in an intramolecular hydrogen-interaction, showed more prominent anti-inflammatory activity modulating, in vivo, the edema formation, the inflammatory infiltration and cytokine levels. An immunomodulatory activity also was observed in these molecules. Thus, our results suggest that imines with these characteristics presents potential to control inflammatory disorders.
• 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.
• Synthesis, spectral, dna binding and cleavage properties of ruthenium(II) Schiff base complexes containing PPh3/AsPh3 as co-ligands
  作者：Subbaiyan Sathiyaraj、Ganesan Ayyannan、Chinnasamy Jayabalakrishnan

  DOI：10.2298/jsc121201073s

  日期：——

  A dihydroxybenzaldehyde Schiff base ligands (L1-L3) and its ruthenium(II) complexes, have been synthesized and characterized on the basis of elemental analysis, 1H, 13C, 31P NMR, mass spectra, UV-vis and IR spectra. The binding of ruthenium(II) complexes have been investigated by UV-vis absorption spectroscopy. The experiment reveals that all the compounds can bind to DNA through an electrostatic mode and intrinsic binding constant (Kb) has been estimated under similar set of experimental conditions. Absorption spectral study indicate that the ruthenium(II) complexes has intrinsic binding constant in the range of 1.6-8.6 X 104 M-1. The complex [Ru(CO)(PPh3)2(L3)] bind more strongly than that of the other complexes. In addition, DNA cleavage property were tested for all ruthenium(II) complexes.

  一种二羟基苯甲醛希夫碱配体（L1-L3）及其钌(II) 配合物的元素分析、1H、13C、31P NMR、质谱、UV 分析、1H、13C、31P NMR、质谱、紫外-可见光谱和红外光谱。与 钌（II）络合物的结合情况进行了研究。 光谱进行了研究。实验表明，所有化合物都能通过静电模式和本征模式与 DNA 结合。 通过静电模式与 DNA 结合。 在类似的实验条件下估算出了本征结合常数（Kb）。吸收光谱 吸收光谱研究表明，钌（II）配合物的本征结合常数在 1.6-6.5 之间。 范围为 1.6-8.6 X 104 M-1。其中[Ru(CO)(PPh3)2(L3) 的结合力比其他复合物更强。此外，对所有 裂解特性进行了测试。