Use of synthetic equivalents of dipolar [C2] 2/2+ -synthons for synthesis of biologically active heterocyclic assemblies with coumarin links

S. N. Kovalenko; Коваленко С. Н.; V. P. Chernykh; Черных В. П.; Ya. V. Belokon; Белоконь Я. В.; I. V. Orlenko; Орленко И. В.; I. A. Zhuravel; Журавель И. А.; V. M. Nikitchenko; Никитченко В. М.; A. V. Silin; Силин А. В.

doi:10.17816/kazmj100584

Use of synthetic equivalents of dipolar [C2] 2/2+ -synthons for synthesis of biologically active heterocyclic assemblies with coumarin links

Authors: Kovalenko S.N.¹, Chernykh V.P.¹, Belokon Y.V.¹, Orlenko I.V.¹, Zhuravel I.A.¹, Nikitchenko V.M.¹, Silin A.V.¹
Affiliations:
1. Ukrainian Pharmaceutical Academy
Issue: Vol 76, No 3 (1995)
Pages: 189-193
Section: Pharmacy
URL: https://journals.rcsi.science/kazanmedj/article/view/100584
DOI: https://doi.org/10.17816/kazmj100584
ID: 100584

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Abstract

Within the synthon approach the analysis of synthetical potential of the dipolar [C₂] 2/2⁺ - synthons is performed. The possible reaction pathways of cyclization of the dipolar electrophilic ${[C_{2}]}_{2}^{2 +}$ -synthons with the dipolar nucleophilic ${[S N]}_{3}^{2 -}$ , ${[S N]}_{4}^{2 -}$ , ${[C N]}_{3}^{2 -}$ , ${[N_{2}]}_{3}^{2 -}$ -synthons are determined. As synthetical equivalents of ${[C_{2}]}_{2}^{2 +}$ -synthons, 3-(α-bromoacetyl) coumarins are chosen. On the basis of the new and improved methods of syntheseis two- and threelink biologically active assemlies of cycles with terminal coumarin links containing thriazole, indolizine, azoindolizine, 1, 3, 4-thiadiazine, furane, quinoxaline and oxazole rings are synthesized. The biological activity of 3-thiazolylcoumarins is investigated. It is stated that all of the compounds under investigation are low toxic and some of them manifest the pronounetd diuretic, antiinflammatory and membrane-stabilizing activities.

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Kazan Medical Archiv

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Department of Organic Chemistry

Russian Federation, Kharkov

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2. Fig. 1. Scheme for the formation of 2,4-substituted thiazoles

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3. Fig. 2. Scheme for the formation of 4-(coumarinyl-3)thiazolyl-2-oxamine and 4-(coumarinyl-3)thiazolyl-2-succinamic acids

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4. Fig. Fig. 3. Scheme of formation of 3-hetarylcoumarins with oxazole, quinoxaline, and furan nuclei.

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