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

Oliveira, Fabrício Marques de; Barbosa, Luiz C. A.; Demuner, Antônio J.; Maltha, Célia R. A.; Pereira, Silvana R.; Horta, Lívia P.; Modolo, Luzia V.

doi:10.1007/s00044-014-1113-y

Cited by 15 publications

(9 citation statements)

References 39 publications

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“…This class of compounds also presents other biological activities, such as antimalarial activity [152] , insecticide activity [153] , [154] , antiHCV activity [155] , antiHIV activity [156] , [157] , and inhibitors of reverse transcriptase [158] and hepatitis C virus [159] . Due the clinical relevance of this class of compounds, Oliveira and co-workers [160] synthesized 25 new phosphoramidates ( Scheme 52 ) and screened their inhibitory activity towards urease isolated from Jack bean. The most active compounds ( 138 to 142 ; Scheme 52 ) showed the properties expected for drug-like compounds, qualifying them to have good pharmacokinetics and drug bioavailability.…”

Section: Organic Substances As Urease Inhibitorsmentioning

confidence: 99%

A review on the development of urease inhibitors as antimicrobial agents against pathogenic bacteria

Rego

Queiroz

Brito

et al. 2018

Journal of Advanced Research

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Section: Organic Substances As Urease Inhibitorsmentioning

confidence: 99%

A review on the development of urease inhibitors as antimicrobial agents against pathogenic bacteria

Rego

Queiroz

Brito

et al. 2018

Journal of Advanced Research

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“…Recently, our group has described that phosphoramidate, benzothiazole and benzoylthiourea compounds are also promising urease inhibitors. [10][11][12] Up to now, phosphorodiamide and phosphorotriamide derivatives Vol. 27, No.…”

Section: Introductionmentioning

confidence: 99%

Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes

Horta¹,

Mota²,

Barbosa³

et al. 2016

J. Braz. Chem. Soc.

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The plant phenolic natural products (PNPs) protocatechuic aldehyde, syringaldehyde and vanillin were used as platforms for obtaining four urease inhibitors. Urea (urease substrate) or thiourea (urease inhibitor) core was added to the structure of newly synthesized compounds to provide inhibitors up to 230-fold more active than the PNPs they originated from. The PNP derivatives are mixed inhibitors with higher affinity to urease active site. Two compounds were as efficient as N-(butyl)thiophosphoric triamide (NBPT) toward soil. Overall, PNPs derivatives are promising urease inhibitors for use as additive in urea-based fertilizers formulations.

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“…The benzoquinones 1–12 were subjected to an in vitro assay using a purified Canavalia ensiformis (jack bean) type III urease to assess their antiureolytic potential. Hydroxyurea ( HU ), commonly used in in vitro screening, was employed as a reference of urease inhibitor. The percentages of urease inhibition caused by all compounds at 5 μ m are displayed in Table .…”

Section: Resultsmentioning

confidence: 99%

“…During the last two decades, a large array of metals and organic substances have been found to inhibit urease. Amongst synthetic organic compounds, the most actives include phosphoramidates, thioureas, dimeric vanadium complexes, benzothiazoles, coumarinyl pyrazolinyl thioamides and dihydropyrimidin(thi)one . Several classes of plant‐derived compounds, including terpenoids, phenolic acids, flavonoids, stilbenes, xanthones, coumarins alkaloids and quinones, among others, have preceding last years, special attention has focused on quinones due to their wide array of biological properties, specially antiureolytic activity .…”

Section: Introductionmentioning

confidence: 99%

Antiureolytic Activity of Substituted 2,5‐Diaminobenzoquinones

Nain-Pérez

Barbosa

Rodríguez-Hernández

et al. 2019

Chemistry & Biodiversity

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A series of 2,5-bis(alkyl/arylamino)-1,4-benzoquinones (1-12) were investigated in vitro for their potential to inhibit the activity of jack bean urease. Compounds 1 -6, 8, 9, 11 and 12 effectively inhibited the jack bean urease activity by 90.8 % when tested at 5 μM, whereas 7 and 10 had relatively little effect. The IC 50 for most compounds was in the nanomolar range (31.4 nM and 36.0 nM for 2 and 8, respectively). The mechanism of enzyme inhibition shown by 2 and 8 is typical of mixed-type inhibitors, whose affinity for the active site is over 6-and 2-fold higher (K i = 30.0 and 22.8 nM, for 2 and 8, respectively) than that of an allosteric site. Molecular docking studies revealed that both 2 and 8 establish hydrogen bonds with the amino acids residues Asp494, Met588, His593 and Ala636 in the active site of jack bean urease. These results indicate that such aminoquinones are useful leads for the development of more efficient urease inhibitors of wider utility. Scheme 1. Structures of 2,5-bis(alky/arylamino)-1,4-benzoquinones used in this study.

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

Cited by 15 publications

References 39 publications

A review on the development of urease inhibitors as antimicrobial agents against pathogenic bacteria

A review on the development of urease inhibitors as antimicrobial agents against pathogenic bacteria

Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes

Antiureolytic Activity of Substituted 2,5‐Diaminobenzoquinones

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