Synthesis and Pharmacological Activity of 2-Methoxyphenyl-Substituted 9-Dialkylaminoethylimidazo[1,2-a]benzimidazoles

Anisimova, V. A.; Спасов, А. А.; Косолапов, В. А.; Kucheryavenko, A. F.; Островский, О. В.; Larionov, N. P.; Libinzon, R.E.

doi:10.1007/s11094-006-0005-y

Cited by 18 publications

(16 citation statements)

References 12 publications

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“…All starting materials and solvents were obtained from commercial suppliers and used as obtained. Compounds 2a [43], 2b [44], 2c [45], 2d [46], 2e [47], and 2f [48] were prepared according to the published procedures. Microwave synthesis: WBFY-201 apparatus.…”

Section: Experimental Partmentioning

confidence: 99%

Novel Disubstituted Phenylene‐Linked Bis‐imidazole Derivatives: Facile Synthesis and Optical Properties

Song

Zhu

Chen

et al. 2010

Helvetica Chimica Acta

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Six novel disubstituted phenylene-linked bis-imidazole derivatives, 3a -3f, were prepared by a onepot, microwave-assisted method under solvent-free conditions, in yields ranging from 61.6 to 85.6%. The new compounds were characterized by 1 H-and 13 C-NMR, UV/VIS, and fluorescence spectroscopy, and mass spectrometry, as well as by elemental analyses. The influence of substituents and solvents on the optical properties of 3a -3f was investigated. It was found that there is little influence on absorption and excitation spectra in contrast to emission spectra. Compounds 3a -3f exhibit strong fluorescence in solution, their fluorescence quantum yields ranging from 0.27 to 0.96. [14 -18]. Among these molecular fluorophores, phenylene-linked bis-imidazole derivatives have been used due to their unique optical properties [19 -21]. In addition, they can be used in two-photon fluorescence and as pH probe [22] [23]. To the best of our knowledge, several reports on the synthesis and on the physical properties of tetrasubstituted phenylene-linked bis-imidazole compounds have been published [24 -29], and the synthesis of phenylene-linked bis-imidazole compounds was only accomplished by condensation of 1,2-dicarbonyl compounds and aldehydes with NH 3 . However, to our surprise, studies on the synthesis and optical properties of disubstituted phenylene-linked bis-imidazole compounds were limited. In 1975, Mahadik and Sunthankar [30] reported the synthesis of some N,N'-disubstituted phenylene-linked bis-imidazoles with yields of 50 -60%. Since then, there were no reports on these compounds, except for the one of Jadhav and co-workers [24] in 2008, who described the synthesis of 2,2'-(1,4-phenylene)bis[5-phenyl-1H-imidazole] only, without giving any optical properties. Considering the above reports, the synthesis of novel disubstituted phenylene-linked bis-imidazoles and the study of the underlying structure -property relationships was a challenge.In this article, a microwave-assisted and solvent-free method for the synthesis of 5-aryl-substituted phenylene-linked bis-imidazoles is reported, involving condensation of benzene-1,4-dicarboximidamidium dichloride with 1-aryl-2-bromoethanones in the presence of using KHCO 3 as acid-binding agent. The six novel disubstituted phenylenelinked bis-imidazole derivatives 3a -3f were synthesized, characterized, and their optical properties investigated.

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Section: Experimental Partmentioning

confidence: 99%

Novel Disubstituted Phenylene‐Linked Bis‐imidazole Derivatives: Facile Synthesis and Optical Properties

Song

Zhu

Chen

et al. 2010

Helvetica Chimica Acta

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“…3,4-Dimethoxyphenacylbromide was ob-tained via bromination of the corresponding acetophenone in ethanol as described for 4-methoxyacetophenone [10]. The acetylation of 2,6-di-tert-butylphenol was performed in excess acetyl chloride at -10°C in the presence of anhydrous aluminum chloride [11]; 3,5-di-tert-butyl-4-hydroxy-w-bromoacetophenone was obtained via the reaction between equivalent amounts of bromine and the corresponding acetophenone in octane or isooctane [12,13].…”

Section: Experimental Chemical Partmentioning

confidence: 99%

Synthesis and pharmacological activity of aroylmethyl derivatives of tricyclic benzimidazole systems containing hydroxy groups in aroyl radicals

et al. 2007

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The synthesis and pharmacological properties of a series of aroylmethyl derivatives of tricyclic benzimidazole systems containing hydroxy groups in aroyl radicals are described. It is established that most of the synthesized compounds exhibit a high antioxidant activity, possess pronounced hemorheological properties, and influence the blood glucose level.The treatment of various pathological states accompanied by the intensification of peroxidation processes [1 -3] usually involves antioxidants [4 -6]. In continuation of the search for new substances possessing antioxidant properties, we have synthesized a series of aroylmethyl derivatives of 2,3-dihydroimidazo-and 2,3,4,10-tetrahydropyrimido-[1, 2-a]benzimidazoles containing various phenolic substituents in the aroyl radical (II -V) and their open forms, representing 2-hydroxyalkylaminobenzimidazoles with 3,5-ditert-butyl-4-hydroxyphenacyl radical in position 1 (IXa, IXb). The synthesized compounds were characterized with respect to antioxidant properties and some other pharmacological effects on various models involving activation of the free-radical processes (in particular, those influencing blood rheology).Compounds II -V can be obtained by directly introducing acylmethyl groups into tricycles Ia and Ib with the aid of the corresponding substituted phenacylbromides.In contrast to smoothly proceeding reactions of tricycles Ia and Ib with 3,5-di-tert-butyl-4-hydroxyphenacylbromide leading to derivatives IV and V, the reactions with 4-hydroxy-and 3,4-dihydroxyphenacylbromides are rather ambigu-ous. These reactions yield ketones II and III heavily contaminated with resinous products, which can be separated neither by recrystallization nor by column chromatography (because of their low mobility). However, using the saponification of methoxy groups in N-para-methoxyphenacyl derivatives of these heterocycles (described in [7]) and in 4-hydroxy-and 3,4-dihydroxyphenacyl derivatives VI in concentrated NBr, we obtained the target products II and III in a rather pure form and with good yields. The restoration of ketones IV and VI by sodium borohydride in MeOH or EtOH yielded alcohols VII and VIII, respectively. n = 1 (Ia -VIIa), 2 (Ib -VIIb, IXa), 3 (IXb); Ar = C 6 H 4 OH-4 (II); C 6 H 3 (OH) 2 -3,4 (III); 3,5-di-tert-butyl-4-hydroxyphenyl (IV, V*, VIII, IX), C 6 H 3 (OCH 3 ) 2 (VI, VII); * Compound Vb contains Me groups in positions 7 and 8.

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“…Method B. A mixture of 4 g (10 mmole) of 2-amino-1-diethylaminoethyl-3-(4-methoxyphenacyl)benzi midazolium bromide (obtained as described in [10] via the interaction of equivalent amounts (10 mmole) of amine VIa and 4-oxyphenacylbromide in 25 ml of acetone) with 100 ml of 48% HBr was boiled for 3 h and cooled. The precipitate was separated by filtration, washed with acetone, and recrystallized to obtain 4.2 g of compound Ia(Br) in the form of snow-white silky whiskers identical to the crystals synthesized using method A. IIIc(Br)…”

Section: Experimental Chemical Partmentioning

confidence: 99%

“…However, the reactions involving oxy-substituted phenacylhalogenides are accompanied by strong resinification, which decreases the product yield to 32 -56%. A more convenient and effective reaction pathway in this case is via cyclization of quaternary salts VII (containing methoxy(dimethoxy)phenacyl groups in position 3 of the benzimidazole nucleus [10]) with simultaneous saponification of methoxy groups, which is achieved by boiling in 48% HBr. In this case, the yields of the corresponding oxy-(dioxy)phenyl substituted benzimidazoles reach 82 -98%.…”

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Synthesis and biological activity of 9-dialkylaminoethyl-2-oxy(dioxy)-phenylimidazo[1,2-a]benzimidazoles

et al. 2006

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A series of 9-dialkylaminoethyl-2-oxy(dioxy)phenylimidazo[1,2-a]benzimidazoles have been synthesized and their pharmacological properties have been studied. Some compounds exhibit pronounced antioxidant activity, as confirmed on experimental pathological models in animals. The tests also revealed membranotropic, spasmolytic, antiaggregant, hemorheological, anticalmodulin, antiulcer, and hypotensive activity, and the properties of serotonin 5-HT 2 and 5-HT 3 receptor antagonists. The results confirm good prospects for the synthesis and screening of biologically active substances among benzimidazoles of this series. 521 0091-150X/06/4010-0521

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Synthesis and Pharmacological Activity of 2-Methoxyphenyl-Substituted 9-Dialkylaminoethylimidazo[1,2-a]benzimidazoles

Cited by 18 publications

References 12 publications

Novel Disubstituted Phenylene‐Linked Bis‐imidazole Derivatives: Facile Synthesis and Optical Properties

Novel Disubstituted Phenylene‐Linked Bis‐imidazole Derivatives: Facile Synthesis and Optical Properties

Synthesis and pharmacological activity of aroylmethyl derivatives of tricyclic benzimidazole systems containing hydroxy groups in aroyl radicals

Synthesis and biological activity of 9-dialkylaminoethyl-2-oxy(dioxy)-phenylimidazo[1,2-a]benzimidazoles

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