Synthesis and Biological Activity of 5-alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1H-pyrazoles

Халиуллин, Ф. А.; Клен, Е. Э.; Павлов, В. Н.; Самородов, А. В.; Шепилова, Светлана Олеговна; Makarova, N. N.; Nurlanova, S. N.; Abzalilov, T. N.

doi:10.1007/s11094-022-02636-9

Cited by 3 publications

(2 citation statements)

References 12 publications

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“…The biological and therapeutic properties of 5-amino-pyrazoles as well as their flexibility in synthetic processes have recently drawn a lot of attention and given them a prominent position 19 . The -NH 2 functionality makes 5-amino-pyrazoles one of a class of adaptable aromatic heterocycles containing nitrogen that have a high degree of controllability for creating different synthesis schemes.…”

Section: Introductionmentioning

confidence: 99%

A new class of anticancer activity with computational studies for a novel bioactive aminophosphonates based on pyrazole moiety

Baren,

Ibrahim,

Al-Rooqi

et al. 2023

Sci Rep

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The present study involves synthesis a new series of α-aminophosphonates 2a-f and 4a-d derivatives in good yield with a simple workup via Kabachnik-Fields reaction in the presence of lithium perchlorate as Lewis acid catalyst. All the newly synthesized compounds were confirmed using various physical, spectroscopic, and analytical data. The in vitro anticancer activities of each compound were evaluated against colorectal carcinoma Colon cancer (HCT-116) and Epdermoid carcinoma (HEP2) and also Human lung fibroblast normal cell line (WI38) compared with Doxorubicin. The results showed that Compounds 2a, 4b and 4d exhibited more potent inhibitory activity for Epdermoid Carcinoma (HEP2) compared with doxorubicin. For colon carcinoma cells (HCT-116) Compounds 2a, 2d and 4b gave the strongest activity among all compounds compared with doxorubicin. Moreover, all designed structures were docked into the active site of VEGFR2 and FGFR1 proteins. The result reveals that compound 2b and have the strongest inhibitory activity of the VEGFR2 and FGFR1 proteins indicating that these substances might conceivably operate as VEGFR2 and FGFR1 inhibitors and hence might take role in anticancer activities with various binding interactions. The 3D-QSAR models produced strong statistical results since they were defined by PLS factors 4 and confirmed by parameters as R2, R2 CV, Stability, F-value, P-value, RMSE, Q2, and Pearson-r.

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Section: Introductionmentioning

confidence: 99%

A new class of anticancer activity with computational studies for a novel bioactive aminophosphonates based on pyrazole moiety

Baren,

Ibrahim,

Al-Rooqi

et al. 2023

Sci Rep

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show abstract

“…Учитывая, что лекарственные средства, созданные на основе комбинации веществ с известной фармакологической активностью и новых химических структур, могут приобретать более выраженную фармакологическую активность или проявлять совершенно иные биологические свойства, поиск в их ряду новых молекул-кандидатов в лекарства теоретически оправдан [29]. Это было подтверждено исследованиями, выполненными в БГМУ: установлено, что тиетан-содержащие гетероциклические соединения обладают гипотензивной [30], противовоспалительной [31], иммунотропной [32], гипогликемической [33], гемореологической [34], антиагрегационной [35], антиоксидантной [36], гепатопротективной активностью [37,38].…”

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Prospects for the creation of new drug candidates with antidepressant activity among thietanes

Nikitina,

Gaisina,

Klen

et al. 2023

Kazan Med J

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The article presents the results of systematic studies on the search for new biologically active molecules with antidepressant activity in the series of thietane-containing heterocyclic compounds and 3-substituted thietane dioxides. The used strategy for the search for antidepressant substances, based on in vivo pharmacological screening in combination with in silico methods of mathematical modeling and toxico-pharmacokinetic evaluation, is described. Studies of the biological activity of thietane-containing reaction products of azoles with thiiranes have been carried out in the series of thietanylimidazoles, titanixanthines, thietanyltriazoles, thietanyltriazolones, and 3-substituted thietane-1,1-dioxides (more than 300 compounds have been studied). The main results of the preclinical evaluation of promising drug candidates with antidepressant activity, 3-methoxythiethane-1,1-dioxide and 3-ethoxythiethane-1,1-dioxide, are presented. Both 3-substituted thietane-1,1-dioxides are characterized by low toxicity when administered intraperitoneally to mice (class IV low toxicity), the absence of toxic risks (mutagenic, carcinogenic, reproductive toxicity, local irritant action), high pharmaceutical potential (compliance with the rule of five Lipinsky), a wide range of action and pronounced antidepressant activity, not inferior to the reference drug amitriptyline (10 mg/kg), confirmed in highly valid in vivo models of depressive-like states (chronic mild stress and resident intruder). In tests of neuropharmacological interaction, it was found that the proposed mechanism of action of 3-substituted thietane-1,1-dioxides is associated with stimulation of 5-HT1A receptors, blockade of 5-HT2A/2C receptors and/or 2-adrenergic receptors. The need for further research is substantiated in order to create domestic first in class antidepressants on their basis.

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Synthesis of Fully Substituted Pyrazoles with a Dicyanomethyl Group via DBU/Lewis Acid-Mediated Annulation of D–A Cyclopropanes with Arylhydrazines

Li,

Cheng,

et al. 2024

J. Org. Chem.

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The efficient synthesis of fully substituted pyrazoles with a dicyanomethyl group was developed via an annulation reaction of 2-aroyl D–A cyclopropanes with arylhydrazines in the presence of DBU/AlCl3 reaction systems. This synthetic approach featured a wide range of readily available aroyl-substituted D–A cyclopropanes with diverse functional groups and a diversity of substituents on pyrazole products and had operationally simple and mild reaction conditions.

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Synthesis and Biological Activity of 5-alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1H-pyrazoles

Cited by 3 publications

References 12 publications

A new class of anticancer activity with computational studies for a novel bioactive aminophosphonates based on pyrazole moiety

A new class of anticancer activity with computational studies for a novel bioactive aminophosphonates based on pyrazole moiety

Prospects for the creation of new drug candidates with antidepressant activity among thietanes

Synthesis of Fully Substituted Pyrazoles with a Dicyanomethyl Group via DBU/Lewis Acid-Mediated Annulation of D–A Cyclopropanes with Arylhydrazines

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