A series of phosphonoamidates and phosphonoamidines derivatives have been prepared with high yields and their conformations were determined. All compounds were characterized by IR, NMR Spectroscopy (1H, 13C, and 31P) and in some cases by elemental analysis and evolution study by 31P-NMR in an external lock with D2O. A DFT calculations studies was performed to identify the stability of all forms (Cis and Trans) (Syn and Anti) at the B3LYP/6-311G** level. The most stable geometry with an Anti-conformation. A comparison with the experimental results validates the level of theory. The biological activity of dimethyl cyclohexyl carbamoylphosphonate (MAmP) and diethyl cyclohexyl carbamoylphosphonate (EAmP) was evaluated. Only the association of ethyl group with phosphorus in amide gives antimicrobial capacity against S. aureus. The evaluation of the analgesic activity following a thermal stimulus showed that the rats treated with the MAmP do not present any sensation of pain. The MAmP molecule had a dose-dependent significant analgesic activity comparable to morphine effect. The hot plate test showed that the EAmP had a significant analgesic effect less than morphine and MAmP. The new compounds at low dose treatment cause an increase in the sensation of pain following a chemical stimulation that induces inflammation. So the EAmP and the MAmP can be morphemic molecules. The morphine mediates a proinflammatory phenotype and induces hyperalgesia. The MAmP was characterized by analgesic activity comparable to morphine and the EAmP was characterized by specific antimicrobial activity against S. aureus.
Electrochemically driven P-H oxidation and functionalization: Synthesis of carbamoylphosphonates from phosphoramides and alcohols
An electrochemical method to achieve carbamoylphosphonates from phosphoramides and alcohols via P-H oxidation and functionalization by using n-Bu4NI as a catalyst is reported. A series of carbamoylphosphonates were obtained with good to excellent yields under mild reaction conditions. The electrochemical reaction is carried out under constant current electrolysis, with the alcohol being used as a solvent and a substrate, and is an attractive green synthesis method.
Iodine-Promoted Rapid Construction of Carbamoylphosphonates from Phosphinecarboxamides
Organic phosphonates and their derivatives are an important class of compounds in a variety of fields, especially medicinal chemistry, materials chemistry, agrochemistry and catalysis. For example, phosphonate esters and carbamoylphosphonates are matrix m
Synthesis, characterisation and thermal decomposition of carbamoylphosphonates
A series of carbamoylphosphonates (1-11) have been synthesised by the direct reaction of isocyanates with dialkyl phosphites catalysed by sodium metal The compounds have been characterised on the basis of their analytical and spectral data. Their thermal
Raza,Khullar,Agarwal, Seema,Jaiswal
p. 154 - 156
(2007/10/03)
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