Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles
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:...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Belgorod National Research University
2022-08-01
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| Series: | Research Results in Pharmacology |
| Online Access: | https://rrpharmacology.ru/article/85498/download/pdf/ |
| _version_ | 1797423492131454976 |
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| author | Alexander A. Spasov Anastasia A. Brigadirova Olga N. Zhukovskaya Anatoly S. Morkovnik Yuliya V. Lifanova |
| author_facet | Alexander A. Spasov Anastasia A. Brigadirova Olga N. Zhukovskaya Anatoly S. Morkovnik Yuliya V. Lifanova |
| author_sort | Alexander A. Spasov |
| collection | DOAJ |
| description | 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: |
| first_indexed | 2024-03-09T07:47:49Z |
| format | Article |
| id | doaj.art-5aaf0b3b253b4dbaac1834e3abc04a20 |
| institution | Directory Open Access Journal |
| issn | 2658-381X |
| language | English |
| last_indexed | 2024-03-09T07:47:49Z |
| publishDate | 2022-08-01 |
| publisher | Belgorod National Research University |
| record_format | Article |
| series | Research Results in Pharmacology |
| spelling | doaj.art-5aaf0b3b253b4dbaac1834e3abc04a202023-12-03T02:33:50ZengBelgorod National Research UniversityResearch Results in Pharmacology2658-381X2022-08-0183414810.3897/rrpharmacology.8.8549885498Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazolesAlexander A. Spasov0Anastasia A. Brigadirova1Olga N. Zhukovskaya2Anatoly S. Morkovnik3Yuliya V. Lifanova4Volgograd State Medical UniversityVolgograd State Medical UniversityInstitute of Physical and Organic Chemistry of the Southern Federal UniversityInstitute of Physical and Organic Chemistry of the Southern Federal UniversityVolgograd State Medical UniversityIntroduction: 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:https://rrpharmacology.ru/article/85498/download/pdf/ |
| spellingShingle | Alexander A. Spasov Anastasia A. Brigadirova Olga N. Zhukovskaya Anatoly S. Morkovnik Yuliya V. Lifanova Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles Research Results in Pharmacology |
| title | Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles |
| title_full | Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles |
| title_fullStr | Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles |
| title_full_unstemmed | Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles |
| title_short | Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles |
| title_sort | search for compounds with antioxidant and antiradical activity among n9 substituted 2 biphenyl 4 yl imidazo 1 2 a benzimidazoles |
| url | https://rrpharmacology.ru/article/85498/download/pdf/ |
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