PUBLICATION

Synthesis and Biological Activity of Schiff Base Series of Valproyl, N-Valproyl Glycinyl, and N-Valproyl-4-aminobenzoyl Hydrazide Derivatives

Authors
El-Faham, A., Farooq, M., Khattab, S.N., Elkayal, A.M., Ibrahim, M.F., Abutaha, N., Wadaan, M.A., Hamed, E.A.
ID
ZDB-PUB-140603-11
Date
2014
Source
Chemical & pharmaceutical bulletin   62: 591-9 (Journal)
Registered Authors
Keywords
none
MeSH Terms
  • Angiogenesis Inhibitors/chemical synthesis
  • Angiogenesis Inhibitors/chemistry
  • Angiogenesis Inhibitors/pharmacology*
  • Animals
  • Antineoplastic Agents/chemical synthesis
  • Antineoplastic Agents/chemistry
  • Antineoplastic Agents/pharmacology*
  • Cell Proliferation/drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Hep G2 Cells
  • Humans
  • Hydrazines/chemical synthesis
  • Hydrazines/chemistry
  • Hydrazines/pharmacology*
  • Molecular Structure
  • Neovascularization, Physiologic/drug effects*
  • Schiff Bases/chemical synthesis
  • Schiff Bases/chemistry
  • Schiff Bases/pharmacology*
  • Structure-Activity Relationship
  • Valproic Acid/analogs & derivatives
  • Valproic Acid/chemical synthesis
  • Valproic Acid/pharmacology*
  • Zebrafish
PubMed
24881666 Full text @ Chem. Pharm. Bull.
Abstract
Series of Schiff bases of valproic acid hydrazide, N-valproylglycine hydrazide and N-valproyl-4-aminobenzoyl hydrazide derivatives were synthesized and characterized by IR, NMR ((1)H- and (13)C-NMR) and elemental analysis. The prepared compounds were evaluated in transgenic zebrafish embryos (Tg: flil-1: enhanced green fluorescent protein (EGFP)) for antiangiogenic activity and in HepG2 liver carcinoma cell line for anti cancer activity. The Schiff bases of N-valproylglycine hydrazide derivatives were most potent in term of suppressing angiogenic blood vessels formation and anticancer activity at very low concentration, followed by the Schiff bases of valproic acid hydrazide derivatives which exhibited moderate activity, while the Schiff bases of N-valproyl-4-aminobenzoyl hydrazide derivatives, ethyl 4-(2-propylpentanamido)benzoate (VABE) and N-(4-(hydrazinecarbonyl)phenyl)-2-propylpentanamide (VABH) in contrast exhibited pro-angiogenic activity and weaker anticancer activity which mean that these derivatives targeted a common signaling pathway in term of affecting the blood vessels formation.
Genes / Markers
Figures
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Antibodies
Orthology
Engineered Foreign Genes
Mapping