Simplified synthesis of dazoxiben

Кочергин, П. М.; Palei, R. M.; Balandina, L. V.; Kharitonova, A. E.; Кравченко, Ангелина Н.; Persanova, L. V.; Govorukhina, E. I.; Frolova, M. A.

doi:10.1007/bf02226528

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“…The initial b-phenoxyethylbromide was synthesized as described in [10]; 4-(b-bromoethoxybenzoic acid and its methyl ester were obtained using a method described in [9]. 9-(2-Phenoxyethyl)-2,3-dihydroimidazo[1,2-a]benzimidazole hydrobromide (IIa × HBr).…”

Section: Experimental Chemical Partmentioning

confidence: 99%

“…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.…”

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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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Section: Experimental Chemical Partmentioning

confidence: 99%

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confidence: 99%