Synthesis of Novel Pyrazolo[3,4-d][1,2,3]Triazines

Gurenko, A. O.; Khutova, B. M.; Klyuchko, S. V.; Василенко, А. Н.; Броварец, В. С.

doi:10.1007/s10593-014-1503-6

Cited by 8 publications

(3 citation statements)

References 14 publications

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“…Concerning the chemical reactivity of azole‐annulated 1,2,3‐triazinones, it has been found that modifications at the carbonyl group lead to 4‐substituted azolo‐triazines,, , alkylation at N‐3 and opening of the triazine ring with elimination of nitrogen afford pyrazole derivatives or pyrazolyl‐pyrazolo‐oxazinones by the dimerization of an iminoketene intermediate , . However, the study of nitrogen‐loss reactions of azolotriazines as an approach to preparing new heterocycles has not been so widely explored, despite the synthetic potential of the precursors.…”

Section: Introductionmentioning

confidence: 99%

Thermal Ring‐Opening of Pyrazolo[3,4‐d][1,2,3]triazin‐4‐ones: An Experimental and Theoretical Study

et al. 2018

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Several 3‐pyrazolylcarbonyl‐pyrazolo[3,4‐d][1,2,3]triazin‐4‐ones have been prepared from 5‐amino‐1H‐pyrazole‐4‐carbonitriles through a simple sequence. In the first step, diazotization of the corresponding aminopyrazoles afforded pyrazolo[3,4‐d][1,2,3]triazin‐4‐ones. Next, thermal rearrangement of these compounds through nitrogen elimination gave the final products. The proposed mechanism for the ring‐opening of the pyrazolotriazinones to give the pyrazolylcarbonyl‐pyrazolotriazinones involves the generation of an iminoketene intermediate, which reacts with a second molecule of pyrazolotriazinone. The complete mechanism of product formation involving the iminoketene intermediate, and all other reasonable pathways, have been explored in detail through DFT calculations. Furthermore, additional experiments to corroborate the presence of the iminoketene intermediate were carried out.

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Section: Introductionmentioning

confidence: 99%

Thermal Ring‐Opening of Pyrazolo[3,4‐d][1,2,3]triazin‐4‐ones: An Experimental and Theoretical Study

et al. 2018

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“…and CS 2 (2.0 Eq.) were slowly added, into small portions, according to the method reported in the literature [121][122][123][124], which was adapted to our synthesis in terms of the ratio of reagents, solvent, time of reaction and purification method. The mixture was stirred for 3 h under reflux till hydrogen sulfide formation was stopped.…”

Section: General Procedures For the Synthesis Of The (Halidealkyl)phenoxy Nitrates (5a-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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“…These compounds were synthesized at the Department for Chemistry of Bioactive Nitrogen-Containing Heterocyclic Compounds of Institute of Bioorganic Chemistry and Petrochemistry of NAS of Ukraine. The methods of synthesis of these heterocyclic compounds are described in the works [67][68][69][70][71].…”

Section: Chemicalsmentioning

confidence: 99%

Screening of Five and Six-Membered Nitrogen-Containing Heterocyclic Compounds as New Effective Stimulants of Linum Usitatissimum L. Organogenesis in Vitro

VA¹,

OO²,

V³

et al. 2016

IJMBG

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Synthesis of Novel Pyrazolo[3,4-d][1,2,3]Triazines

Cited by 8 publications

References 14 publications

Thermal Ring‐Opening of Pyrazolo[3,4‐d][1,2,3]triazin‐4‐ones: An Experimental and Theoretical Study

Thermal Ring‐Opening of Pyrazolo[3,4‐d][1,2,3]triazin‐4‐ones: An Experimental and Theoretical Study

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

Screening of Five and Six-Membered Nitrogen-Containing Heterocyclic Compounds as New Effective Stimulants of Linum Usitatissimum L. Organogenesis in Vitro

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