potassium (N-2-hydroxyacetophenone)glycinate | 147389-32-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: potassium (N-2-hydroxyacetophenone)glycinate
• 英文别名: Potassium-2-{[(e)-1-(2-hydroxyphenyl) ethylidene]-amino}acetate；potassium;2-[1-(2-hydroxyphenyl)ethylideneamino]acetate
• CAS: 147389-32-0
• 化学式: C₁₀H₁₀NO₃*K
• 分子量: 231.293
• InChiKey: QWFISNQFQJCQKT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.34
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium (N-2-hydroxyacetophenone)glycinate 、 nickel(II) sulfate hexahydrate 以 乙醇 、 水 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  A newly synthesized nickel chelate can selectively target and overcome multidrug resistance in cancer through redox imbalance both in vivo and in vitro

  摘要：

  Induction of undesired toxicity and emergence of multidrug resistance (MDR) are the major obstacles for cancer treatment. Moreover, aggressive cancers are less sensitive towards existing chemotherapeutics. Therefore, selective targeting of cancers without inducing undesired side effects and designing proper strategies to overcome MDR has utmost importance in modern chemotherapy. Previously we revealed the anticancer properties of some transition metal chelates of Schiff base, but the effectiveness of nickel complex is still unrevealed. Herein, we synthesized and characterized a Schiff base nickel chelate, nickel-(II) N-(2-hydroxyacetophenone) glycinate (NiNG), through different spectroscopic means. NiNG proves to be a broad spectrum anticancer agent with considerable efficacy to overcome MDR in cancer. Antiproliferative effects of NiNG was evaluated using drug-resistant (CEM/ADR5000; NIH-MDR-G185; EAC/Dox), drug-sensitive aggressive (Hct116; CCRF-CEM; EAC/S) and normal (NIH-3T3) cells that reveal the selective nature of NiNG towards drug resistant and sensitive cancer cells without inducing any significant toxicity in normal cells. Moreover, NiNG involves reactive oxygen species (ROS)-mediated redox imbalance for induction of caspase 3-dependent apoptosis in aggressive drug-sensitive Hct116 and drug-resistant NIH-MDR-G185 cells through disruption of mitochondrial membrane potential. Moreover, intraperitoneal (i.p.) application of NiNG at non-toxic doses caused significant increase in the life-span of Swiss albino mice bearing sensitive and doxorubicin-resistant subline of Ehrlich ascites carcinoma cells. It is noteworthy that, in vitro NiNG can only overcome P-glycoprotein-mediated MDR while in vivo NiNG can overcome MRP1-mediated MDR in cancer. Therefore, NiNG has therapeutic potential to target and overcome MDR in cancer.

  DOI：

  10.1007/s00775-017-1498-4
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 聚甘氨酸 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以75%的产率得到potassium (N-2-hydroxyacetophenone)glycinate
  参考文献：
  名称：

  Synthesis, characterization and biological properties of a novel copper complex

  摘要：

  The study of copper complex in relation to cancer is important in many ways. A novel copper complex has been synthesized with non toxic ligand, viz. potassium salt of N-(2-hydroxy acetophenone) glycinate (NHAG). The structure of the complex has been determined by spectroscopic means. Toxicity and antitumor property of the complex has been studied in vivo. Though the complex is toxic at higher doses, lower non toxic doses of the complex deplete glutathione (GSH). GSH depleting property of the complex may be utilized to sensitize drug resistant cells where resistance is due to elevated level of GSH.

  DOI：

  10.1016/j.ejmech.2003.08.002

文献信息

• Chauhan, H. P. S.; Bhargava, A.; Rao, R. J., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1993, vol. 32, # 1-3, p. 157 - 160
  作者：Chauhan, H. P. S.、Bhargava, A.、Rao, R. J.

  DOI：——

  日期：——
• Synthesis, characterization and biological evaluation of a novel vanadium complex as a possible anticancer agent
  作者：Abhinaba Sinha、Kaushik Banerjee、Arpita Banerjee、Satyajit Das、Soumitra Kumar Choudhuri

  DOI：10.1016/j.jorganchem.2014.08.032

  日期：2014.12

  Chemotherapeutics are the sole treatment modality for cancer patients at advanced condition. In the pursuit of getting an efficient, selective and non toxic anticancer agent that has not been discovered yet, we rationally synthesized a vanadium complex with a Schiff base ligand N-(-2-hydroxyacetophenone) glycinate. Characterization of the synthesized complex VO(NG)(2), was carried out with the help of various spectroscopic means. The complex proved to be a broad spectrum anticancer agent with significantly less toxicity towards normal cells as evident from cell viability assay. Furthermore, VO(NG)(2) treatment increased the life-span of ascitic and solid tumor bearing Swiss albino mice and did not show any significant symptomatic sub acute toxicity on normal Swiss albino mice. (c) 2014 Elsevier BY. All rights reserved.
• Parekh; Pansuriya; Patel, Polish Journal of Chemistry, 2005, vol. 79, # 12, p. 1843 - 1851
  作者：Parekh、Pansuriya、Patel

  DOI：——

  日期：——
• Synthesis, structural characterization, and antifungal activity of Schiff bases and their transition metal mixed-ligand complexes
  作者：Hitesh M. Parekh、Saurabh R. Mehta、M. N. Patel

  DOI：10.1134/s003602360601013x

  日期：2006.1

  Mixed-ligand complexes of Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) have been prepared with biologically active Schiff bases, viz. potassium salt of o-hydroxyacetophenoneglycine [KHL] and bis(benzylidene)ethylenediamine [A(1)] or thiophene-o-carboxaldene-p-toluidine [A(2)]. The synthesized mixed-ligand complexes have been characterized on the basis of elemental analysis, thermogravimetric analysis, magnetic measurements, and electronic and infrared spectra. The mixed-ligand complexes show higher antifungal activity as compared to the free ligands, metal salts, and the control (dimethylsulfoxide) but moderate activity as compared to the standard fungicides (bavistin and emcarb).