Design and synthesis of nitrate esters of aromatic heterocyclic compounds as pharmacological preconditioning agents

Fotopoulou, Theano; Iliodromitis, Efstathios K.; Koufaki, Maria; Tsotinis, Andrew; Ζώγα, Αναστασία; Gizas, Vassilis; Pyriochou, Anastasia; Papapetropoulos, Andreas; Andreadou, Ioanna; Kremastinos, Dimitrios Th.

doi:10.1016/j.bmc.2008.02.051

Cited by 12 publications

(12 citation statements)

References 46 publications

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“…Nitrogen heterocyclic compounds : The synthesis of the nitrate esters of the heteroaromatic compounds (MK55, MK56, MK94, and MK129) was previously described . N ‐(2‐Nitrooxyethyl)‐1 Η ‐indole‐2‐carboxamide (MK55), Ν ‐(2‐nitrooxyethyl)‐quinoline‐2‐carboxamide (MK56), Ν ‐(2‐nitrooxyethyl)‐6‐(piperidin‐1‐yl)‐9 H ‐purine acetamide (MK94), and 5′‐ Ο ‐nitroadenosine (MK129) were the subjects of investigation (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

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Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors

et al. 2018

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Four heteroaromatic compounds bearing nitrate esters were selected using a virtual-screening procedure as putative sterol 14α-demethylase (CYP51) Candida albicans inhibitors. Compounds were examined for their inhibition on C. albicans growth and biofilm formation as well as for their toxicity. NMR spectroscopy studies, in silico docking, and molecular dynamics simulations were used to investigate further the selectivity of these compounds to fungal CYP51. All compounds exhibited good antimicrobial properties, indicated with low minimal inhibitory concentrations and ability to inhibit formation of fungal biofilm. Moreover, all of the compounds had the ability to inhibit growth of C. albicans cells. N-(2-Nitrooxyethyl)-1Η-indole-2-carboxamide was the only compound with selectivity on C. albicans CYP51 that did not exhibit cytotoxic effect on cells isolated from liver and should be further investigated for selective application in new leads for the treatment of candidiasis.

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Section: Methodsmentioning

confidence: 99%

“…Synthesis Nitrogen heterocyclic compounds:T he synthesis of the nitrate esters of the heteroaromatic compounds (MK55, MK56, MK94, and MK129) was previously described. [9,10]…”

Section: Methodsmentioning

confidence: 99%

Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors

et al. 2018

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“…All compounds were administered as bolus injections in a total dose of 3.8 μmol/kg, at the 20th min of ischaemia and at the first minute of reperfusion. Doses were chosen based on previous results in a similar experimental model where we demonstrated that other purine analogues in a total dose of 3.8 μmol/kg reduced infarct size when administered prior or during sustained ischaemia [23,24]. ( S )‐PHPNECA was first administered in this specific dose to evaluate its efficacy and hemodynamic effects in our in vivo model of ischaemia/reperfusion.…”

Section: Methodsmentioning

confidence: 99%

Pharmacological postconditioning of the rabbit heart with non-selective, A1, A2A and A3 adenosine receptor agonists

Bibli

Iliodromitis

Lambertucci

et al. 2014

Journal of Pharmacy and Pharmacology

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“…was added. The mixture was stirred under reflux and darkness for approximately 12 h, according to the methods reported in the literature [110][111][112][113][114][115][116][117], which were adapted to our synthesis in terms of the ratio of reagents, solvent, time of reaction, purification method. At the end of the reaction, brine was added to precipitate the excess of silver nitrate.…”

Section: General Procedures For the Synthesis Of The (Hydroxyalkyl)phenoxy Nitrates (4a-p)mentioning

confidence: 99%

Design, Synthesis, In Silico and In Vitro Studies for New Nitric Oxide-Releasing Indomethacin Derivatives with 1,3,4-Oxadiazole-2-thiol Scaffold

Sava

Buron

Routier

et al. 2021

IJMS

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Starting from indomethacin (IND), one of the most prescribed non-steroidal anti-inflammatory drugs (NSAIDs), new nitric oxide-releasing indomethacin derivatives with 1,3,4-oxadiazole-2-thiol scaffold (NO-IND-OXDs, 8a-p) have been developed as a safer and more efficient multitarget therapeutic strategy. The successful synthesis of designed compounds (intermediaries and finals) was proved by complete spectroscopic analyses. In order to study the in silico interaction of NO-IND-OXDs with cyclooxygenase isoenzymes, a molecular docking study, using AutoDock 4.2.6 software, was performed. Moreover, their biological characterization, based on in vitro assays, in terms of thermal denaturation of serum proteins, antioxidant effects and the NO releasing capacity, was also performed. Based on docking results, 8k, 8l and 8m proved to be the best interaction for the COX-2 (cyclooxygense-2) target site, with an improved docking score compared with celecoxib. Referring to the thermal denaturation of serum proteins and antioxidant effects, all the tested compounds were more active than IND and aspirin, used as references. In addition, the compounds 8c, 8h, 8i, 8m, 8n and 8o showed increased capacity to release NO, which means they are safer in terms of gastrointestinal side effects.

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Design and synthesis of nitrate esters of aromatic heterocyclic compounds as pharmacological preconditioning agents

Cited by 12 publications

References 46 publications

Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors

Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors

Pharmacological postconditioning of the rabbit heart with non-selective, A1, A2A and A3 adenosine receptor agonists

Design, Synthesis, In Silico and In Vitro Studies for New Nitric Oxide-Releasing Indomethacin Derivatives with 1,3,4-Oxadiazole-2-thiol Scaffold

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