Synthesis, molecular properties and DFT studies of new phosphoramidates as potential urease inhibitors

In this work, new phosphoramidates were prepared and screened for their putative urease inhibitory activity. The importance of this class of compounds is related to the wide range of biological activities which they exhibit. Consequently, higher activity shown by phosphoramidates 3a , 4b , 5a , 5b ,...

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Published inMedicinal chemistry research Vol. 23; no. 12; pp. 5174 - 5187
Main Authors Oliveira, Fabricio M., Barbosa, Luiz C. A., Demuner, Antônio J., Maltha, Célia R. A., Pereira, Silvana R., Horta, Lívia P., Modolo, Luzia V.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.12.2014
Subjects
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Original Research
Pharmacology/Toxicology
Urease inhibitors
Phosphoramidates
Canavalia ensiformis
DFT Studies
Jack bean urease
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Summary:In this work, new phosphoramidates were prepared and screened for their putative urease inhibitory activity. The importance of this class of compounds is related to the wide range of biological activities which they exhibit. Consequently, higher activity shown by phosphoramidates 3a , 4b , 5a , 5b , 5c , and 9a suggests that they could serve as lead substances for the development of novel synthetic compounds with enhanced inhibitory ureolitic activity. Their predicted ADMET properties are also in accordance with the general requirements for drug-like compounds. Structure–activity relationship analyses suggest that the presence of cyclohexylamine group is an important structural feature associated with enhanced activities. DFT calculations were performed to obtain the energy values of HOMO and LUMO, and dipole moment.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-014-1113-y