1-Substituted 2-Benzylaminobenzimidazoles with Phenyl Methoxyls: Synthesis, Computer Prediction, and Pharmacological Activity

Zhukovskaya, O. N.; Anisimova, V. A.; Spasov, A. A.; Vasil’ev, P. M.; Косолапов, В. А.; Kucheryavenko, A. F.; Гурова, Н. А.; Науменко, Л. В.; Кузнецова, В. А.; Sorotskii, D. V.; Соловьева, Ольга Александровна; Резников, Евгений Владимирович; Gurova, V. V.; Сиротенко, В. С.

doi:10.1007/s11094-016-1362-9

Cited by 5 publications

(4 citation statements)

References 6 publications

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“…Derivatives of 9-R-2-halogenophenyl-IMBI had a pronounced inhibitory effect on the processes of lipid peroxidation comparable to dibunol [15]. The compounds from the series of 1-substituted 2-benzylaminobenzimidazoles with phenyl methoxyls acted similarly [20]. Amides of 2,3-dihydroimidazo-and 2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazolyl-acetic acids showed moderate AO activity compared to dibunol [18].…”

Section: The Resultsmentioning

confidence: 93%

“…Condensed benzimidazole derivatives were synthesized, and experimental screening of the antioxidant activity of new chemical compounds was carried out among the derivatives of 2-(hetaryl) imidazo[1,2-a]benzimidazoles (IMBI) [5], 3-aroyl-and 3-hetaroyl-IMBI [6], 2-methoxyphenyl-substituted 9-dialkylaminoethyl-IMBI [7], 2-methoxy-phenyl-and 2-oxyphenyl-substituted 1-dialkylaminoalkyl-IMBI [8], N-acylmethyl derivatives of 9H-2,3-dihydro-IMBI and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles [9], 9-dialkylaminoethyl-2-oxy(dioxy)phenyl-IMBI [10], aroylmethyl derivatives of tricyclic benzimidazole systems containing hydroxy groups in aroyl radicals [11] [17], amides of 2,3-dihydroimidazo-and 2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazolyl-acetic acids [18], phenyl-and alkylthiocarbamides of 2,9-disubstituted IMBI [19], and 1-substituted 2-benzylaminobenzimidazoles with phenyl methoxyls [20]. Butylated hydroxytoluene (BHT, CAS Number 128-37-0), also known as dibunol, was chosen as a comparative drug.…”

Section: The Resultsmentioning

confidence: 99%

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Condensed Benzimidazoles Are a Novel Scaffold for Antioxidant Agents’ Search and Development

Косолапов¹,

Спасов²,

Анисимова³

et al. 2019

Antioxidants

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Taking into account that the imidazole ring has π-electron redundancy, condensed benzimidazole derivatives have attracted our attention as a promising class for the search for antioxidant substances. Synthesis was carried out, and information on the antioxidant activity of imidazo-and tetrahydropyrimido benzimidazoles was provided. Highly active antioxidant substance enoxifol has been revealed. The data on the synthesis and study of the pharmacodynamic, pharmacokinetic, and toxicological properties of the new antioxidant compound enoxifol are presented. The antioxidant activity of the compound is due to its ability to inactivate superoxide, hydroxyl, and peroxyl radicals, thereby reducing the overall oxidation rate due to a decrease in the total initiation rate. It has been shown that enoxifol has hepatoprotector, antihypoxic, cerebroprotective, nootropic, stressprotective, neuropsychotropic, actoprotective, cardioprotective, antiaggregant, and antithrombogenic properties and is able to prevent rheological disorders in diabetes mellitus.

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Section: The Resultsmentioning

confidence: 93%

Section: The Resultsmentioning

confidence: 99%

Condensed Benzimidazoles Are a Novel Scaffold for Antioxidant Agents’ Search and Development

Косолапов¹,

Спасов²,

Анисимова³

et al. 2019

Antioxidants

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“…Антиоксидантные свойства конденсированных производных бензимидазола были изучены ранее [8,9] на модели аскорбат-зависимого ПОЛ. Было показано, что наибольшую антиоксидантную активность проявляли производные 9-диалкиламиноэтил-имидазобензимидазола (ИМБИ) с 3,4-диоксифенильным заменителем, которые в два раза превосходили препарат сравнения дибунол.…”

Section: Introductionunclassified

Antihypoxic properties of condensed benzimidazole derivatives with antioxidant activity

Спасов

Алексеевич²,

Косолапов

et al. 2019

Rev Clin Pharm Drug Ther

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Hypoxia plays an important role in the vital activity of the organism and practically accompanies any pathology. Hypoxia and tissue ischemia in the early stages are accompanied by the activation of lipid peroxidation. Derivatives of 9-dialkylaminoethyl imidazobenzimidazole with a 3,4-dioxyphenyl substitute showed high antioxidant activity. Therefore, they have been studied for antihypoxic activity in experimental models of hypobaric, histotoxic and hemic hypoxia, as well as in animals pre-typed for resistance to hypoxia, and it was shown that new condensed benzimidazole derivatives with antioxidant activity showed a wide range of antihypoxic activity. The most pronounced protective antihypoxic properties were demonstrated by compound RU-185.

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“…The presence of not one but two "privileged" fragments in the molecules of these compounds, namely, imidazoles, benzimidazoles and biphenyl should promote multitarget action. We also collected and analyzed the data on the activity of the synthesized biphenyl compounds with respect to a number of biological targets important for the therapy of diabetes mellitus and its vascular complications [33][34][35][36]. In view of these observations and in continuation of our research work on biologically active biphenyl derivatives, it is proposed to synthesize substituted biphenyl acid-amide derivatives by the condensation of 4-biphenyl acetic acid precursor first with thionyl chloride (to make its acid chloride) and then with different primary amines (aliphatic or aromatic).…”

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confidence: 99%

Studies and Synthesis of Substituted 4-Biphenyl Acetamide Derivatives

Khullar¹

2019

Asian J. Chem.

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A new series of substituted 4-biphenylamides have been synthesized by condensation of 4-biphenyl acetic acid with different primary amines (aromatic and aliphatic). 4-Biphenyl acetic acid was first treated with thionyl chloride in dry benzene to prepare substituted 4-biphenyl acetyl chloride, which is then treated with different aliphatic or aromatic amines to synthesize various substituted 4-biphenyl acid-amide derivatives. The structure of newly synthesized compounds has been established by analytical and spectral methods. These synthesized compounds have shown antifungal properties against Fusarium udum and Curvularia lunata.

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1-Substituted 2-Benzylaminobenzimidazoles with Phenyl Methoxyls: Synthesis, Computer Prediction, and Pharmacological Activity

Cited by 5 publications

References 6 publications

Condensed Benzimidazoles Are a Novel Scaffold for Antioxidant Agents’ Search and Development

Condensed Benzimidazoles Are a Novel Scaffold for Antioxidant Agents’ Search and Development

Antihypoxic properties of condensed benzimidazole derivatives with antioxidant activity

Studies and Synthesis of Substituted 4-Biphenyl Acetamide Derivatives

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