Synthesis, Crystal Structures, and in Silico Toxicity Prediction of Thienopyridine Phosphoramidates

Pedrosa, Leandro F.; Macedo, William P. de; Furtado, Antonia Carlene Rodrigues; Guedes, Guilherme P.; Pinheiro, Luiz C. S.; Resende, Jackson A. L. C.; Vaz, Maria G. F.; Bernardino, Alice M. R.; Souza, Marcos C. de

doi:10.1080/00397911.2013.786092

Cited by 7 publications

(3 citation statements)

References 44 publications

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“…Intramolecular hydrogen bonding between ester O4 oxygen and N2 amine atoms was also observed. Furthermore, dimers of molecules raised due to the intermolecular hydrogen bonding involving the phosphoramidate O1 and N1 atoms (Figure 2), as previously reported for this compound class 34 ( Table 2). Symmetry code: (i) −x+2, −y+1, −z.…”

Section: Introductionsupporting

confidence: 60%

“…[3,4-b]pyridine phosphoramidates 8a-l showed in their decoupled 31 P NMR spectra one signal in the region between 7.01-7.60 ppm, typical for phosphoramidates. [31][32][33][34] Furthermore, infrared spectra exhibited strong absorptions for the P=O at 1269-1263 cm Single crystals of compound 8j suitable for X-ray diffraction were obtained by slow solvent evaporation at room temperature. The crystal data and structure refinement parameters for this compound are provided (See Supplementary Material, Table S1).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of new 1H-pyrazolo[3,4-b]pyridine phosphoramidate derivatives

Pedrosa¹,

Macedo²,

Furtado³

et al. 2014

Arkivoc

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Twelve new 1H-pyrazolo [3,4-b]pyridine phosphoramidate derivatives were synthesized under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-Cl substituted pyrazolo [3,4-b]pyridine in good yields. The new compounds were characterized by IR, 1 H, 13 C and 31 P NMR spectroscopy and HRMS. The crystal structure of one compound was solved by X-ray diffraction and showed a network of intermolecular interactions involving phosphoramidate groups.

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Section: Introductionsupporting

confidence: 60%

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new 1H-pyrazolo[3,4-b]pyridine phosphoramidate derivatives

Pedrosa¹,

Macedo²,

Furtado³

et al. 2014

Arkivoc

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“…It is used for evaluating the potential of the drug candidate. When the drug score is better, then the compound is predictive to be a drug candidate [ 26 ]. The drug score value of standard celecoxib is found to contain 0.37.…”

Section: Resultsmentioning

confidence: 99%

3-D structural interactions and quantitative structural toxicity studies of tyrosine derivatives intended for safe potent inflammation treatment

Puratchikody

Sriram

Umamaheswari

et al. 2016

Chemistry Central Journal

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BackgroundDrugs that inhibit cyclooxygenase-2 (COX-2) while sparing cyclooxygenase-1 (COX-1) represent a new attractive therapeutic development and offer new perspective for further use of COX-2 inhibitors. Intention of this work is to develop safer, selective COX-2 inhibitors that do not produce harmful effects.ResultsA series of 55 tyrosine derivatives were designed for evaluation as selective COX-2 inhibitors and investigated by in silico for their anti-inflammatory activities using C-Docker. The results of docking study showed that 35 molecules were found to selectively inhibit the enzyme COX-2. These molecules formed stable π hydrophobic and additional van der Waals interactions in the active site side pocket of COX-2. The molecules selected from docking studies were examined through ADMET descriptors and Osiris property explorer to find its safety profile as well. The tyrosine derivatives containing toxic fragments were eliminated.ConclusionThe results conclude that out of 55, 19 molecules possessed best binding energy (< −3.333 kcal/mol) and these molecules had more selective and safer COX-2 inhibitor profile compared to the standard celecoxib.Graphical abstract3-D structural interactions of COX-2 inhibiting tyrosine derivatives.

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ChemInform Abstract: Synthesis, Crystal Structures, and in silico Toxicity Prediction of Thienopyridine Phosphoramidates.

et al. 2014

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Synthesis, Crystal Structures, and in Silico Toxicity Prediction of Thienopyridine Phosphoramidates

Cited by 7 publications

References 44 publications

Synthesis and characterization of new 1H-pyrazolo[3,4-b]pyridine phosphoramidate derivatives

Synthesis and characterization of new 1H-pyrazolo[3,4-b]pyridine phosphoramidate derivatives

3-D structural interactions and quantitative structural toxicity studies of tyrosine derivatives intended for safe potent inflammation treatment

ChemInform Abstract: Synthesis, Crystal Structures, and in silico Toxicity Prediction of Thienopyridine Phosphoramidates.

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