2-Amino-3,5-dicarbonitrile-6-sulfanylpyridines: synthesis and multiple biological activity – a review

Akhmadiev, Nail S.; Ибрагимов, А. Г.

doi:10.1039/d1ra00363a

Cited by 9 publications

(4 citation statements)

References 98 publications

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“…With this aim, we decided to synthesize a new nanomagnetic organic‐inorganic hybrid of porphyrin Fe 3 O 4 @SiO 2 @(CH 2 ) 3 ‐GO‐[PTTA‐NH−Ni]. On the other hand, a literature survey shows that the chemistry of pyridines and pyrimidines has great demand and is extensively reviewed [45–49] . Also, we decided to synthesize these compounds in the presence of described catalyst due to their biological activity and abilities for the development of anomeric‐based oxidation (ABO).…”

Section: Resultsmentioning

confidence: 99%

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Application of New Magnetic Graphene Oxide‐Porphyrin Nanoparticles for Synthesis of Pyridines and Pyrimidines via Anomeric‐Based Oxidation

et al. 2022

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Herein joining of poly graphene oxide‐porphyrin to magnetic nanoparticles {poly Fe3O4@SiO2@(CH2)3‐GO‐[PTTA‐NH−Ni] MNPs} was occurred. The synthesized catalyst was characterized by several techniques such as FT‐IR, CHN elemental analysis, EDX, WDX elemental maps, TGA, DTG, DTA, XRD, FE‐SEM, TEM, BET, BJH, VSM, and ICP‐AES. The described magnetic nanoparticles were employed as a benign catalyst for the expedient synthesis of 5‐amino‐7‐aryl‐2‐oxo‐2,3‐dihydrothiazolo[4,5‐b] pyridine‐6‐carbonitriles via anomeric‐based oxidation mechanistic pathway. Target molecules were prepared through a four‐component reaction of 2,4‐thiazolidinedione, aldehydes, malononitrile, and ammonium acetate under solvent‐free conditions at 75 °C. Also, the application of the presented catalyst was investigated under the same reaction conditions for the synthesis of 5,7‐diaryl‐4,7‐dihydro‐[1,2,4]triazolo[1,5‐a]pyrimidines through the three‐component reaction of aldehydes, acetophenones, and 3‐amino‐1,2,4‐triazole.

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Section: Resultsmentioning

confidence: 99%

“…On the other hand, a literature survey shows that the chemistry of pyridines and pyrimidines has great demand and is extensively reviewed. [45][46][47][48][49] Also, we decided to synthesize these compounds in the presence of described catalyst due to their biological activity and abilities for the development of anomeric-based oxidation (ABO).…”

Section: Resultsmentioning

confidence: 99%

Application of New Magnetic Graphene Oxide‐Porphyrin Nanoparticles for Synthesis of Pyridines and Pyrimidines via Anomeric‐Based Oxidation

et al. 2022

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“…Pyridine ring system and its analogues show a broad spectrum of physiological and biological activities [7] . Among these, 2‐Amino‐3,5‐dicarbonitrile‐6‐thiopyridine occupies a prominent place as a ‘privileged scaffold’ owing to its latent therapeutic applications in the treatment of Parkinson's disease, the Hepatitis B infections, Creutzfeldt–Jacob disease, cancer, hypoxia / ischemia, epilepsy, and so on and so forth [8,9] . In addition, they are often used as anti‐bacterial and anti‐prion agents [10] .…”

Section: Introductionmentioning

confidence: 99%

Montmorillonite K10 Clay Accelerated One‐Pot Multicomponent Synthesis of Substituted 2‐Amino‐3,5‐dicarbonitrile‐6‐phenylsulfanylpyridines: Experimental and Theoretical Investigation

Sharma,

Sinha

2023

ChemistrySelect

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Abstract2‐Amino‐3,5‐dicarbonitrile‐6‐phenylsulfanylpyridines occupy a prominent place among the physiologically and biologically active scaffolds owing to their therapeutic applications in the treatment of Parkinson's disease, asthma, urinary incontinence, kidney disease, the Hepatitis B infections, Creutzfeldt–Jacob disease, cancer, hypoxia/ischemia and epilepsy. A one‐pot, multicomponent condensation of aldehydes, malononitrile, and thiophenol catalyzed by Montmorillonite K10 clay afforded 2‐amino‐3,5‐dicarbonitrile‐6‐phenylsulfanylpyridines in good to excellent yields. All the products could be well characterized on the basis of spectral studies. The catalyst could be recycled three times without affecting the yields and even in the fourth recycling of the catalyst, the yield decreases marginally. This approach manifests environmentally benign feasibility in contexts of enhanced yields, milder conditions, short reaction times, and reusability of the catalyst. A theoretical study of a synthesized compound at the B3LYP/6–31 + G (d) level is additionally reported. Following the computation of the fundamental vibrational wavenumbers and intensities, it became evident that the observed and calculated wavenumbers were in perfect accord. Employing the same DFT level, Frontier molecular orbital (HOMO‐LUMO) energies, global reactivity descriptors, and molecular electrostatic potential were estimated for assessing the reactivity and possible sites for electrophilic and nucleophilic molecules. The outcomes prove that the compound exhibits significant kinetic stability.

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“…Considering the huge scope of pyridine and its derivatives [28,29], the invention and improvement of new techniques for the synthesis of pyridines have drawn a great deal of chemists interest [30]. A number of approaches have been reported for the construction of pyridine and its derivatives [31][32][33][34][35][36][37][38][39][40][41][42][43].…”

Section: Introductionmentioning

confidence: 99%

An eco‐efficient new path of mortar pestle grinding approach for the construction of methanol and ethylthio substituted pyridines with in silico studies

Edapu,

Boodida,

Pagadala

et al. 2023

Journal of Heterocyclic Chem

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A green and highly regioselective approach for the synthesis of poly‐substituted new pyridine derivatives via the Knoevenagel condensation followed by the Michael addition. The reaction involves intramolecular cyclization of easily obtainable reactants under environmentally and economically benign mortar pestle grinding technique. This method clearly proves that spatially hindered aldehydes also actively contribute to the construction of the desired pyridine derivatives with good yield (85%–96%) in about 30–40 min. This new avenue offers a number of benefits over earlier reaction approaches such as lengthy work‐up‐processes, operational difficulties and lower yields. This mortar pestle grinding technique is familiar for environmental and economical benign protocols. The druggability properties of synthesized compounds assessed using in silico studies.

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2-Amino-3,5-dicarbonitrile-6-sulfanylpyridines: synthesis and multiple biological activity – a review

Abstract: The latest advances in the catalytic synthesis of biologically active compounds with 2-amino-3,5-dicarbonitrile-6-sulfanylpyridine scaffold via the multicomponent reactions of malononitrile have been discussed.

Cited by 9 publications

References 98 publications

Application of New Magnetic Graphene Oxide‐Porphyrin Nanoparticles for Synthesis of Pyridines and Pyrimidines via Anomeric‐Based Oxidation

Application of New Magnetic Graphene Oxide‐Porphyrin Nanoparticles for Synthesis of Pyridines and Pyrimidines via Anomeric‐Based Oxidation

Montmorillonite K10 Clay Accelerated One‐Pot Multicomponent Synthesis of Substituted 2‐Amino‐3,5‐dicarbonitrile‐6‐phenylsulfanylpyridines: Experimental and Theoretical Investigation

An eco‐efficient new path of mortar pestle grinding approach for the construction of methanol and ethylthio substituted pyridines with in silico studies

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