2-Allyloxy/propargyloxypyridines: synthesis, structure, and biological activity

Бабаев, Е. В.; Koval, Y. I.; Рыбаков, В. Б.; Paronikyan, E. G.; Stepanyan, G. M.; Paronikyan, R. G.; Dashyan, Sh. Sh.; Rzhevskii, Sergey A.; Шадрин, И А

doi:10.1007/s11172-018-2076-9

Cited by 4 publications

(3 citation statements)

References 25 publications

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“…[137] Babaev et al synthesized cyanopyridine derivatives 71 a-f and 71 a'-f' (Figure 19) and their biological activities (antimicrobial and anticonvulsant) were analyzed. [138] . When compounds 71 b' and 71 c' were injected at a dose of 100 mg kg À 1 , the study of anticonvulsant activity showed that neither substance prevented convulsions caused by carbazole, however, compound 71 a' prevented seizures in 40 % of animals.…”

Section: Anticonvulsantmentioning

confidence: 99%

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Pharmacological Perspectives of 2‐alkoxy‐3‐Cyanopyridine Scaffolds: An Up‐to‐Date Review

Mahesha,

Shetty

2024

ChemistrySelect

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The 2‐alkoxy‐3‐cyanopyridine derivatives’ straightforward synthesis, ease of structural manipulation, and variety of intriguing biological activity continue to captivate medicinal chemists. A substantial body of research has demonstrated that these derivatives exhibit several intriguing biological characteristics, including anticancer, antibacterial, antidiabetic, antioxidant, vasorelaxant, antiviral, and anti‐inflammatory effects. Based on the basic skeleton of 2‐alkoxy‐3‐cyanopyridine, some lead compounds have been prepared with varied pharmaceutical characteristics. These served as excellent models for the development of novel medications since they showed potential in vitro and in vivo action against several cell lines that were both drug‐susceptible and drug‐resistant. To expand the use of 2‐alkoxy‐3‐cyanopyridine in biomedicine, though, a lot more efforts are essential. To combat medication resistance and boost specificity, potential hybrids that unite the 2‐alkoxy‐3‐cyanopyridine moiety with other pharmacophores are indeed required. This review offers a summary of pharmacological screening, including studies of pertinent structure‐activity connections, action mechanisms, and potential therapeutic use.

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Section: Anticonvulsantmentioning

confidence: 99%

“…Babaev et al . synthesized cyanopyridine derivatives 71 a – f and 71 a’ – f’ (Figure 19) and their biological activities (antimicrobial and anticonvulsant) were analyzed [138] …”

Section: Biological Activitymentioning

confidence: 99%

Pharmacological Perspectives of 2‐alkoxy‐3‐Cyanopyridine Scaffolds: An Up‐to‐Date Review

Mahesha,

Shetty

2024

ChemistrySelect

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“…On the other hand, tetracyclic fused systems containing pyran, pyridine, thiophene and pyrimidine rings can be considered analogues of heterosteroids, which are known to display varied biological effects [ 15 , 16 , 17 ]. Moreover, literature data evidenced that bi-, tri-, tetra- and pentacyclic systems containing pyridine and pyrimidine rings were endowed with neurotropic properties [ 18 , 19 , 20 ], and the addition of a cycle does not reduce biological activity.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Neurotropic Activity and Molecular Docking Study of New Derivatives of pyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines on the Basis of pyrano[3,4-c]pyridines

Dashyan¹,

Бабаев

Paronikyan³

et al. 2022

Molecules

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Background: Heterocyclic compounds and their fused analogs, which contain pharmacophore fragments such as pyridine, thiophene and pyrimidine rings, are of great interest due to their broad spectrum of biological activity. Chemical compounds containing two or more pharmacophore groups due to additional interactions with active receptor centers usually enhance biological activity and can even lead to a new type of activity. The search for new effective neurotropic drugs in the series of derivatives of heterocycles containing pharmacophore groups in organic, bioorganic and medical chemistry is a serious problem. Methods: Modern methodology of drugs involves synthesis, physicochemical study, molecular modeling and selection of active compounds through virtual screening and experimental evaluation of the biological activity of new chimeric compounds with pharmacophore fragments. For the synthesis of new compounds, classical organic methods were used and developed. For the evaluation of neurotropic activity of new synthesized compounds, some biological methods were used according to indicators characterizing anticonvulsant, sedative and antianxiety activity as well as side effects. For docking analysis,various soft ware packages and methods were used. Results: As a result of multistep reactions, 11 new, tri- and tetracyclic heterocyclic systems were obtained. The studied compounds exhibit protection against pentylenetetrazole (PTZ) seizures as well as some psychotropic effects. The biological assays evidenced that nine of the eleven studied compounds showed a high anticonvulsant activity by antagonism with pentylenetetrazole. The toxicity of the compounds is low, and they do not induce muscle relaxation in the studied doses. According to the study of psychotropic activity, it was found that the selected compounds have an activating behavior and anxiolytic effects on the “open field” and “elevated plus maze” (EPM) models. The data obtained indicate the anxiolytic (antianxiety) activity of the derivatives of tricyclic thieno[2,3-b]pyridines and tetracyclic pyridothieno[3,2-d]pyrimidin-8-ones, especially pronounced in compounds 3bf and 4e. The studied compounds increase the latent time of first immobilization on the “forced swimming” (FS) model and exhibit antidepressant effects; compounds 3e and 3f especially exhibit these effects, similarly to diazepam. Docking studies revealed that compounds 3c and 4b bound tightly in the active site of γ-aminobutyric acid type A (GABAA) receptors with a value of the scoring function that estimates free energy of binding (∆G) at −10.0 ± 5 kcal/mol. Compound 4e showed the best affinity ((∆G) at −11.0 ± 0.54 kcal/mol) and seems to be an inhibitor of serotonin(SERT) transporter. Compounds 3cf and 4e practically bound with the groove of T4L of 5HT_1A and blocked it completely, while the best affinity observed was in compound 3f ((∆G) at −9.3 ± 0.46 kcal/mol). Conclusions: Тhe selected compounds have an anticonvulsant, activating behavior and anxiolytic effects and at the same time exhibit antidepressant effects.

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Synthesis of tetracyclic thienotriazolopyridines based on hydrazine derivatives of fused pyridinethiones

et al. 2022

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2-Allyloxy/propargyloxypyridines: synthesis, structure, and biological activity

Cited by 4 publications

References 25 publications

Pharmacological Perspectives of 2‐alkoxy‐3‐Cyanopyridine Scaffolds: An Up‐to‐Date Review

Pharmacological Perspectives of 2‐alkoxy‐3‐Cyanopyridine Scaffolds: An Up‐to‐Date Review

Evaluation of Neurotropic Activity and Molecular Docking Study of New Derivatives of pyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines on the Basis of pyrano[3,4-c]pyridines

Synthesis of tetracyclic thienotriazolopyridines based on hydrazine derivatives of fused pyridinethiones

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