N-(2,4-dihydroxybenzylidene)-1-naphthylamine | 113800-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2,4-dihydroxybenzylidene)-1-naphthylamine
• 英文别名: 4-((naphthalen-1-ylimino)methyl)benzene-1,3-diol；1,3-Benzenediol, 4-[(1-naphthalenylimino)methyl]-；4-(naphthalen-1-yliminomethyl)benzene-1,3-diol
• CAS: 113800-82-1
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: RJBRMIUDYFYKSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• 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：
  3

反应信息

• 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 N-(2,4-dihydroxybenzylidene)-1-naphthylamine
  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.