Synthesis and fluorescence properties of nicotinonitrile 1,2,3-triazole derivatives

Rakshin, S. O.; Odin, I. S.; Sosnin, Ilya M.; Zatynatskiy, E. A.; Ostapenko, Gennady I.; Голованов, А. А.

doi:10.1007/s11172-018-2280-7

Cited by 6 publications

(5 citation statements)

References 31 publications

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“…The fluorescence intensity of all products was determined for solutions of the same concentration (5.0 × 10 –6 M). The procedure for measuring the relative quantum yield (by quinine sulfate) for compound 4l is described in our previous article …”

Section: Methodsmentioning

confidence: 99%

Reactivity of Cross-Conjugated Enynones in Cyclocondensations with Hydrazines: Synthesis of Pyrazoles and Pyrazolines

et al. 2021

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The cyclocondensation of cross-conjugated enynones, dienynones, and trienynones (easily available due to low-cost starting compounds) with arylhydrazines leads to the regioselective synthesis of pyrazole derivatives (dihetaryl-substituted ethens, buta-1,3-diens, and hexa-1,3,5-triens) or results in 4,5-dihydro-1H-pyrazoles in good yield. The reaction path is controlled by the character of the substituent in enynone: the pyrazoles are obtained from the reaction of substrates that contain five-membered heteroaromatic substituents with arylhydrazines, and the 4,5-dihydro-1H-pyrazoles are obtained from the reaction of 1,5-diphenylpent-1-en-4-yn-3-one with arylhydrazines consistently. Despite the presence of a substituent, cyclocondensation of 2-hydrazinylpyridine with all of examined cross-conjugated enynones leads to the formation of pyrazoles. The reaction does not require special conditions (temperature, catalyst, inert atmosphere). The cyclocondensation pathways are determined by the electronic effect of an electron-rich five-membered heteroaromatic ring in the substrate. The synthesis allows use of various substituents and functional groups in enynone and hydrazine. The present method features high yields and simplicity of the product purification. The obtained pyrazoles possess fluorescent properties with a quantum yield up to 31%.

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Section: Methodsmentioning

confidence: 99%

Reactivity of Cross-Conjugated Enynones in Cyclocondensations with Hydrazines: Synthesis of Pyrazoles and Pyrazolines

et al. 2021

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“…In recent research, N -heterocyclic compounds such as nicotinonitriles or triaryl pyridines have been considered for the preparation of various biologically active compounds with antiviral, antibacterial, anticonvulsant, and antioxidant properties, which are also useful in the treatment of breast and lung cancer (Figure ). − Furthermore, changing substitutions at various ring positions of pyridine can also enhance the biological activities of nicotinonitriles. , Therefore, research and development are necessary and important in the synthesis of new compounds with N -scaffold compounds.…”

Section: Introductionmentioning

confidence: 99%

“… 25 − 27 Furthermore, changing substitutions at various ring positions of pyridine can also enhance the biological activities of nicotinonitriles. 28 , 29 Therefore, research and development are necessary and important in the synthesis of new compounds with N -scaffold compounds.…”

Section: Introductionmentioning

confidence: 99%

Application of Nanomagnetic Metal–Organic Frameworks in the Green Synthesis of Nicotinonitriles via Cooperative Vinylogous Anomeric-Based Oxidation

et al. 2023

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In the current study, we synthesized a new nanomagnetic metal− organic framework Fe 3 O 4 @MIL-53(Al)-N(CH 2 PO 3 ) 2 and characterized it using various techniques. This nanomagnetic metal−organic framework was used for the synthesis of a wide range of nicotinonitrile derivatives as suitable drug candidates by a four-component reaction of 3-oxo-3-phenylpropanenitrile or 3-(4-chlorophenyl)-3oxopropanenitrile, ammonium acetate (NH 4 OAc), acetophenone derivatives, and various aldehydes including those bearing electron-donating, electron-withdrawing, and halogen groups, which afforded desired products (27 samples) via a cooperative vinylogous anomeric-based oxidation (CVABO) mechanism under solvent-free conditions in excellent yields (68−90%) and short reaction times (40−60 min). Increasing the surface-to-volume ratio, easy separation of the catalyst using an external magnet, and high chemical and temperature stability are the advantages of the described nanomagnetic metal−organic frameworks.

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“…Recent advancements have spotlighted the significance of nicotinonitrile (3-cyanopyridine) derivatives, primarily due to their multifaceted biological activity [3]. These derivatives have been recognized for their antibacterial [4,5], antitumor [6], anticancer [7], cardiotonic [8], antiviral (specifically against avian influenza) [9], and anticonvulsant properties [10].…”

Section: Introductionmentioning

confidence: 99%

“…Beyond their biological attributes, nicotinonitriles are also renowned for their distinctive photophysical properties [3,12,13], paving the way for their potential applications in nonlinear optics [14], liquid crystal technologies [15], fluorescent molecular switches tailored to metal ion detection [16], and organic light-emitting devices [17].…”

Section: Introductionmentioning

confidence: 99%

Integrated Structural, Functional, and ADMET Analysis of 2-Methoxy-4,6-diphenylnicotinonitrile: The Convergence of X-ray Diffraction, Molecular Docking, Dynamic Simulations, and Advanced Computational Insights

Bakheit,

Alkahtani

2023

Molecules

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This study systematically investigates the molecular structure and electronic properties of 2-methoxy-4,6-diphenylnicotinonitrile, employing X-ray diffraction (XRD) and sophisticated computational methodologies. XRD findings validate the compound’s orthorhombic crystallization in the P21212 space group, composed of a pyridine core flanked by two phenyl rings. Utilizing the three-dimensional Hirshfeld surface, the research decodes the molecule’s spatial attributes, further supported by exhaustive statistical assessments. Key interactions, such as π–π stacking and H⋯X contacts, are spotlighted, underscoring their role in the crystal’s inherent stability and characteristics. Energy framework computations and density functional theory (DFT) analyses elucidate the prevailing forces in the crystal and reveal geometric optimization facets and molecular reactivity descriptors. Emphasis is given to the exploration of frontier molecular orbitals (FMOs), aromaticity, and π–π stacking capacities. The research culminates in distinguishing electron density distributions, aromatic nuances, and potential reactivity hotspots, providing a holistic view of the compound’s structural and electronic landscape. Concurrently, molecular docking investigates its interaction with the lipoprotein-associated phospholipase A2 protein. Notably, the compound showcases significant interactions with the protein’s active site. Molecular dynamics simulations reveal the compound’s influence on protein stability and flexibility. Although the molecule exhibits strong inhibitory potential against Lp-PLA2, its drug development prospects face challenges related to solubility and interactions with drug transport proteins.

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Synthesis and fluorescence properties of nicotinonitrile 1,2,3-triazole derivatives

Cited by 6 publications

References 31 publications

Reactivity of Cross-Conjugated Enynones in Cyclocondensations with Hydrazines: Synthesis of Pyrazoles and Pyrazolines

Reactivity of Cross-Conjugated Enynones in Cyclocondensations with Hydrazines: Synthesis of Pyrazoles and Pyrazolines

Application of Nanomagnetic Metal–Organic Frameworks in the Green Synthesis of Nicotinonitriles via Cooperative Vinylogous Anomeric-Based Oxidation

Integrated Structural, Functional, and ADMET Analysis of 2-Methoxy-4,6-diphenylnicotinonitrile: The Convergence of X-ray Diffraction, Molecular Docking, Dynamic Simulations, and Advanced Computational Insights

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