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Vikulov, A. D.; Melnikov, A. A.; Osetrov, I. A.

doi:10.1023/a:1011928814846

Cited by 6 publications

(4 citation statements)

References 15 publications

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“…The effect of the synthesized compounds upon erythrocyte aggregation was characterized in terms of the erythrocyte aggregation index (EAI) calculated as the ratio of the blood viscosity at a shear rate of 5 sec -1 to that at 100 sec -1 [18].…”

Section: Experimental Pharmacological 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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Section: Experimental Pharmacological 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 blood viscosity was measured (and expressed in cP) on an AKR-2 viscometer (Russia) operating in the range of shear rates from 300 to 3 sec -1 so as to model the blood flow in various vessels [21]. The drug effect upon erythrocyte aggregation was characterized in terms of the aggregation index calculated as the ratio of the blood viscosity at 3 sec -1 to that at 100 sec -1 [22].…”

Section: Experimental Pharmacological Partmentioning

confidence: 99%

Synthesis and biological activity of N-acylmethyl derivatives of 9H-2,3-dihydroimidazo-and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles and their reduction products

et al. 2006

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Section: Experimental Pharmacological Partmentioning

confidence: 99%

Synthesis and pharmacological activity N-aryloxyethyl derivatives of 9H-2,3-dihydroimidazo-and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles

et al. 2006

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A series of N-aryloxyethyl derivatives of 9H-2,3-dihydroimidazo-and 10H-2,3,4,10-tetrahydropyrimido-[1,2-a]benzimidazoles have been synthesized and tested for pharmacological properties. It is established that most of the synthesized substances exhibit antiarrhythmic, antiaggregant and hemorheological activity.Earlier, we reported on the hypoglycemic and antiaggregant properties of derivatives of 9H-2,3-dihydroimidazo-and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles [1,2]. In continuation of the search for new substances possessing high biological activity, we have introduced aryloxyethyl groups into these benzimidazoles and studied the influence of these groups on the properties of the obtained products. n = 1 (Ia, II), 2 (Ib, III); Ar = C 6 H 5 (IIa, IIIa), C 6 H 4 CO-OCH 3 -4 (IIb, IIIb); X = Br, Cl Compounds II and III were synthesized via the interaction of NH-unsubstituted tricycles (Ia, Ib) with b-aroylethylhalogenides. The reactions were carried out under neutral conditions, either with a solvent or without it (i.e., in the melt). Under such conditions, the reactions proceed at the nitrogen atom of pyridine moiety in Ia and Ib heterocycles (which exist both in the solid state and in solutions in the form of 1-NH-tauromers [3,4]) and lead to the formation of N-b-phenoxyethyl-substituted compounds IIa -IIc and IIIa -IIIc. The proposed structures were confirmed by the results of IR and 1 H NMR spectroscopy measurements.Previously, it was established that compounds II and III exhibit local anesthetic activity [5,6]. Taking into account that (i) some well-known local anesthetics (lidocaine, trimecaine, piromecaine) also possess antiarrhythmic properties [7] and (ii) the 2-(4-carboxyphenoxy)ethyl substituent is responsible for the antiaggregant activity of dazoxiben [8,9], we have also tested the newly synthesized aryloxyethyl-substituted compounds II and III in this respect. EXPERIMENTAL CHEMICAL PARTThe course of the reactions was monitored and the purity of the target products was checked by TLC on Al 2 O 3 plates eluted with chloroform (CHCl 3 ) and developed by exposure to iodine vapor in a wet chamber. The yields and some physicochemical characteristics of target compounds are listed in Table 1. The data of elemental analyses agree with the results of analytical calculations according to the corresponding empirical formulas.

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Cited by 6 publications

References 15 publications

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

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

Synthesis and biological activity of N-acylmethyl derivatives of 9H-2,3-dihydroimidazo-and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles and their reduction products

Synthesis and pharmacological activity N-aryloxyethyl derivatives of 9H-2,3-dihydroimidazo-and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles

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