Synthesis and pharmacological activity of 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles

Spasov, A. A.; Zhukovskaya, O. N.; Brigadirova, A. A.; Abbas, Hebat‐Allah S.; Анисимова, В. А.; Sysoeva, V. A.; Rashchenko, A. I.; Mayka, O. Yu.; Babkov, Denis A.; Морковник, А. С.

doi:10.1007/s11172-017-1965-7

Cited by 11 publications

(7 citation statements)

References 33 publications

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“…Interestingly, the SAR study revealed that the compounds' activity against both AMPK and PTP1B shows an inverse correlation with the number of H‐bond acceptors, suggesting that binding might be impaired by repulsive interactions (Figure 3). Generally, activity against both enzyme is strongly associated with the presence of unfunctionalized biphenyl moiety, which corresponds to the previously reported data (Kurundkar et al, 2011; Lan et al, 2017; Spasov, Zhukovskaya, et al, 2017). For PTP1B, N , N ‐dimethylaminoethyl‐ and 2‐piperidinoethyl side chains also benefited the inhibitory activity.…”

Section: Resultssupporting

confidence: 91%

Discovery and evaluation of biphenyl derivatives of 2‐iminobenzimidazoles as prototype dual PTP1B inhibitors and AMPK activators with in vivo antidiabetic activity

et al. 2023

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This work describes the synthesis of series hydrobromides of N-(4-biphenyl) methyl-N′-dialkylaminoethyl-2-iminobenzimidazoles, which, due to the presence of two privileged structural fragments (benzimidazole and biphenyl moieties), can be considered as bi-privileged structures. Compound 7a proved to activate AMP-activated kinase (AMPK) and simultaneously inhibit protein tyrosine phosphatase 1B (PTP1B) with similar potency. This renders it an interesting prototype of potential antidiabetic agents with a dual-target mechanism of action.Using prove of concept in vivo study, we show that dual-targeting compound 7a has a disease-modifying effect in a rat model of type 2 diabetes mellitus via improving insulin sensitivity and lipid metabolism.

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Section: Resultssupporting

confidence: 91%

Discovery and evaluation of biphenyl derivatives of 2‐iminobenzimidazoles as prototype dual PTP1B inhibitors and AMPK activators with in vivo antidiabetic activity

et al. 2023

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“…Mixing tests of these compounds did not show depression with the compounds previously prepared by basic catalyzed cyclization. Physicochemical characteristics of compounds 1a-c,e,f and 2a,b were published in (Spasov et al 2017).…”

Section: Resultsmentioning

confidence: 99%

“…By chemical nature, antioxidants represent a wide class of compounds: phenols and polyphenols (tocopherols, eugenol, pyrocatechol, gallic acid derivatives), flavonoids (rutin, quercetin), steroid hormones (lecithin, cephalin) and many other compounds (Belviranli and Okudan 2015;Neha et al 2019). In addition, the N 9 -substituted imidazo[1,2-a]benzimidazole derivatives, which we are actively studying, also demonstrate antioxidant properties, which allows us to consider this group of compounds as promising for further modification and development of new antioxidants (Anisimova et al 2007(Anisimova et al , 2016Kosolapov et al 2013;Spasov et al 2017).…”

Section: Introductionmentioning

confidence: 99%

Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles

Spasov¹,

Brigadirova²,

Zhukovskaya³

et al. 2022

RRP

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Introduction: Biphenyl and imidazobenzimidazole derivatives attract ongoing attention as a combination of these two privileged substructures with promising pharmacological activities. The aim of this study was to synthesize and investigate in vitro antioxidant activity of promising novel compounds: 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles. Materials and methods: The newly synthesized compounds were characterized by IR, 1H NMR and CHBr(Cl)NO analyses. All newly synthesized compounds were screened for their in vitro antioxidant activity: inhibition of lipid peroxidation (LPO), 2,2’-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) radical cation decolorization and inhibition of hemoglobin (Hb)-H2O2-induced luminol chemiluminescence. Results and discussion: 2-Amino-3-[(2-biphenyl-4-yl)-2-oxo-ethyl)]-1-R-1Н-benzimidazolium bromides were synthesized, and their cyclization into functionalized imidazo[1,2-a]benzimidazole derivatives was studied. The resulting compounds showed LPO inhibitory activity comparable to that of dibunol. Compounds 1a and 1d (see graphical abstract), containing a methyl or dimethylaminoethyl substituent in the N9 position also proved to be equally highly active in the Hb-H2O2-induced luminol chemiluminescence model, while compound 1a was somewhat more active than 1d in the ABTS• radical scavenging assay. Conclusion: The study showed that compounds 1a and 1d have the highest antioxidant activity. Thus, this new class of 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazole derivatives represents a valuable leading series with great potential for use as antioxidants and as promising candidates for further efficacy evaluation. Graphical abstract:

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“…Оптимизация методики медь-индуцированного аутоокисления аскорбиновой кислоты путем внедрения процедуры real-time в процесс регистрации данных. Стандартная операционная процедура: оригинальная методика медь-индуцированного аутоокисления аскорбиновой кислоты предварительно настроена, валидизирована [1] и неоднократно использована коллективом авторов в исследовательской деятельности [10,11].…”

Section: цель работыunclassified

Optimisation of Copper-Induced Ascorbate Autoxidation Method Using Real-Time Detection. Integrative Decision Example

Иванов

Shamshina

Litvinov

et al. 2018

Journal of Volgograd State Medical University

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В данном исследовании описана оптимизация методики медь-индуцированного аутоокисления аскорбиновой кислоты как способа оценки хелатирующей активности веществ на примере пиоглитазона. В процесс регистрации данных была внедрена техника real-time. Анализ данных проведен с применением интегральных исчислений и последующей кластеризацией данных. Это позволило вести более быстрое определение активности и использовать в сравнительном анализе одну концентрацию в противовес стандартному концентрационному исследованию.Ключевые слова: аскорбиновая кислота, многофункциональная антиоксидантность, хелация, сульфат меди (II), исследование в реальном времени.

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Synthesis and pharmacological activity of 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles

Cited by 11 publications

References 33 publications

Discovery and evaluation of biphenyl derivatives of 2‐iminobenzimidazoles as prototype dual PTP1B inhibitors and AMPK activators with in vivo antidiabetic activity

Discovery and evaluation of biphenyl derivatives of 2‐iminobenzimidazoles as prototype dual PTP1B inhibitors and AMPK activators with in vivo antidiabetic activity

Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles

Optimisation of Copper-Induced Ascorbate Autoxidation Method Using Real-Time Detection. Integrative Decision Example

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