The chemistry of aminoguanidine derivatives – preparation, crystal structure, thermal properties, and molecular docking studies of aminoguanidinium salts of several carboxylic acids
| Autor: | Rajendran Selvakumar, Subbaiah Govindarajan, Thathan Premkumar, Steven J. Geib, Aathi Muthu Sankar |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Bicarbonate Oxalic acid Salt (chemistry) General Chemistry Crystal structure Condensed Matter Physics Medicinal chemistry Oxalate chemistry.chemical_compound chemistry Yield (chemistry) Organic chemistry General Materials Science Orthorhombic crystal system Monoclinic crystal system |
| Zdroj: | Journal of Physics and Chemistry of Solids. 86:49-56 |
| ISSN: | 0022-3697 |
| DOI: | 10.1016/j.jpcs.2015.05.024 |
| Popis: | The reaction of aminoguanidine bicarbonate (Amg) with oxamic, oxalic, malonic and sulfoacetic acids yielded (AmgH)H 2 NOC–COO ( 1 ), OOC–CONHNHC(NH 2 )NH 2 ( 2 ) (AmgH)HOOC–CH 2 –COO ( 3 ) and O 3 S–CH 2 –CONHNHC(NH 2 )NH 2 ( 4 ), respectively. For the first time, we studied the salt-forming ability of aminoguanidine with several carboxylic acids, such as oxamic, oxalic, malonic and sulphoacetic acids. We also compared the structural and thermal properties of these salts. Oxamic and malonic acids form only mono-aminoguanidinium salts, whereas oxalic acid mainly forms di-aminoguanidinium oxalate. In addition, oxalic acid forms guanylhydrazido-oxalic acid which exists as zwitter ion. Unlike other acids, sulfoacetic acid readily forms only the zwitter ionic salts (2-guanylhydrazido-oxo-methanesulfonic acid) rather than the usual simple salt. This result may be a result of the highly acidic nature of the sulfonic group, which favors acid catalyzed condensation. More significantly, for the first time, the ability guanylhydrazido-oxalic acid ( 2 ) and 2-guanylhydrazido-oxo-methanesulfonic acid ( 4 ) to inhibit human butyrylcholinesterase (human BChE) receptor has been studied with a molecular docking approach. The binding of the compounds to human BChE was examined as it is crucial to understanding the biological significance of aminoguanidine derivatives. The compounds were identified and characterized by analytical, FT-IR spectroscopic and thermal studies. Furthermore, the structures of compounds 1 , 2 and 4 were confirmed by single X-ray diffraction studies. Compounds 1 and 2 crystallized in a monoclinic crystal system with P2 1 /c and Cc space groups, respectively, whereas compound 4 crystalized in an orthorhombic system with a Pbca space group. All the compounds ( 1–4 ) underwent endo- followed by exothermic decomposition in the temperature range from 130 to 600 °C to yield gaseous products. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect