Antibacterial profile against drug-resistant Staphylococcus epidermidis clinical strain and structure–activity relationship studies of 1H-pyrazolo[3,4-b]pyridine and thieno[2,3-b]pyridine derivatives

Leal, Bruno; Afonso, Ilídio F.; Rodrigues, Carlos Rangel; Abreu, Paula Alvarez; Garrett, Rafael; Pinheiro, Luiz C. S.; Azevedo, A.; Borges, Júlio César; Vegi, Percilene Fazolin; Santos, C.C.C.; Silveira, Francisco C.A. da; Cabral, Lúcio Mendes; Frugulhetti, Izabel C.P.P.; Bernardino, Alice M. R.; Santos, Dilvani Oliveira; Castro, Helena C.

doi:10.1016/j.bmc.2008.07.035

Cited by 63 publications

(40 citation statements)

References 22 publications

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“…A known synthetic approach was used for preparing the 3 H -benzo[ b ]pyrazolo[3,4- h ]-1,6-naphthyridines (1a-k) and 3 H -pyrido[2,3- b ]pyrazolo[3,4- h ]-1,6-naphthyridines (2a-c) , starting from ethyl 4-chloro-1-phenyl-1 H -pyrazolo[3,4- b ]pyridine-5-carboxylate (7) (Scheme 1) [26-28]. In the first step, ethyl α -carboethoxy- β -(5-pyrazolylammonium)acrylate (8) was prepared by the condensation between 5-amino-1-phenyl-1 H -pyrazole (9) and diethyl ethoxymethylenemalonate, in ethanol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and anti-HSV-1 evaluation of new 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridines and 3H-pyrido[2,3-b]pyrazolo[3,4-h]-1,6-naphthyridines

et al. 2012

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BackgroundHerpes simplex virus type-1 (HSV-1) is the primary cause of facial lesions (mouth, lips, and eyes) in humans. The widespread use of acyclovir and nucleoside analogues has led to emergence of HSV strains that are resistant to these drugs. Recently, non-nucleoside anti-HSV compounds have received considerable attention. 1,6-Naphthyridines are a class of heterocyclic compounds that exhibit a broad spectrum of biological activities such as inhibitor of HIV-1 integrase, HCMV, FGF receptor-1 tyrosine kinase, and the enzyme acetylcholinesterase. We previously reported the synthesis, SAR studies, and evaluation anti-HSV-1 activity of 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridines. In the course of our search for new 1,6-naphthyridines derivatives with potential activity against HSV-1, we have synthesized and evaluated new 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridines (1a-k) and 3H-pyrido[2,3-b]pyrazolo[3,4-h]-1,6-naphthyridines (2a-c).ResultsA known synthetic approach was used for preparing new 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridines (1a-k) and 3H-pyrido[2,3-b]pyrazolo[3,4-h]-1,6-naphthyridines (2a-c), starting from ethyl 4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (7). All compounds were identified by FTIR, 1H NMR, and mass spectrometry. The antiviral effect on HSV-1 virus replication was determined.ConclusionsThe compounds 1d, 1f, 1g, and 1h exhibited the highest anti-HSV-1 activity. In general, 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridines were more effective inhibitors than their corresponding 3H-pyrido[2,3-b]pyrazolo[3,4-h]-1,6-naphthyridines. The compound 1h reduced the virus yield in 91% at 50 μM and exhibited a low cytotoxicity (CC50 600 μM).

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Section: Resultsmentioning

confidence: 99%

Synthesis and anti-HSV-1 evaluation of new 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridines and 3H-pyrido[2,3-b]pyrazolo[3,4-h]-1,6-naphthyridines

et al. 2012

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“…In the present work, the physiochemical properties, viz. molecular weight, Log P values, solubility, mutagenicity, Pa (possibility of activity), hydrogen bond acceptors (HBA), hydrogen bond donors (HBD), and drug scores were calculated using online drug-relevant prediction property software (PASS, OSIRIS) 33,34 . Compounds 3b and 3g revealed good dock scores (−84.976 kcal/mol, −90.921 kcal/mol) and drug scores (0.9, 0.79), and therefore are considered to be better inhibitors of XO.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological activity of pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4-one derivatives: in silico approach

Khobragade

Bodade

Dawane

et al. 2009

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Structure-activity relationship studies and molecular docking Molecular modeling calculations were performed as described elsewhere 8,[21][22][23][24] . Briefly, the three-dimensional structure of each derivative was built using SPARTAN (Wavefunction Õ , Irvine, CA) and the geometry optimization was obtained through the RM1 semi-empirical method followed by an ab initio calculation in quantum level using the 6-31G** basis set to obtain all stereoelectronic properties.…”

Section: In Silico Assaysmentioning

confidence: 99%

Antiplatelet pyrazolopyridines derivatives: pharmacological, biochemical and toxicological characterization

Saito

Lourenço

Dias

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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Platelet aggregation is one of the main events involved in vascular thrombus formation. Recently, N 0 -substituted-phenylmethylene-3-methyl-1,6-diphenyl-1H-pyrazolo [3,4-b]pyridine-4-carbohydrazides were described as antiplatelet derivatives. In this work, we explore the properties of these antiplatelet agents through a series of pharmacological, biochemical and toxicological studies. The antiplatelet activity of each derivative was confirmed as 3a, 3b and 3 h significantly inhibited human platelet aggregation induced by arachidonic acid, with no detectable effect on clotting factors or healthy erythrocytes. Importantly, mice treated with derivative 3a showed a higher survival rate at an in vivo model of pulmonary thromboembolism with a lower bleeding risk in comparison to aspirin. The in silico studies pointed a series of structural parameters related to thromboxane synthase (TXS) inhibition by 3a, which was confirmed by tracking plasma levels of PGE 2 and TXB 2 through an in vitro enzyme immunoassay. Derivative 3a showed selective TXS inhibition allied with low bleeding risk and increased animal survival, revealing the derivative as a promising candidate for treatment of cardiovascular diseases.

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Antibacterial profile against drug-resistant Staphylococcus epidermidis clinical strain and structure–activity relationship studies of 1H-pyrazolo[3,4-b]pyridine and thieno[2,3-b]pyridine derivatives

Cited by 63 publications

References 22 publications

Synthesis and anti-HSV-1 evaluation of new 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridines and 3H-pyrido[2,3-b]pyrazolo[3,4-h]-1,6-naphthyridines

Synthesis and anti-HSV-1 evaluation of new 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridines and 3H-pyrido[2,3-b]pyrazolo[3,4-h]-1,6-naphthyridines

Synthesis and biological activity of pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4-one derivatives: in silico approach

Antiplatelet pyrazolopyridines derivatives: pharmacological, biochemical and toxicological characterization

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