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

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 ${\left[C_2\right]}_2^{2+}$ -synthons with the dipolar nucleophilic ${\left[SN\right]}_3^{2-}$, ${\left[SN\right]}_4^{2-}$, ${\left[CN\right]}_3^{2-}$,  ${\left[N_2\right]}_3^{2-}$-synthons are determined. As synthetical equivalents of ${\left[C_2\right]}_2^{2+}$-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.

Keywords

Kazan Medical archive

References

[1] Журавель И. А., Коваленко С. Н. и др.// Сборник трудов Рязанского мед. ин-та.—Рязань, 1991.—С. 75—83

[2] Журавель И. А., Коваленко С. Н. и др.// Фармац. журнал.—1991.—№ 4.—С. 72—76

[3] Машковский М. Д. Лекарственные средства: В 2-х томах. Т. 2—10-е изд. стер.— М., 1986

[4] Ягодинец П. И., Скрипская О. В., Федориев Н. И., Чернюк И. Н.// Деп. Укр. НИИНТИ 22.08.90, № 1391-Ук90

[5] Andreani A., Rambalbi M., Andreani F., Bossa R.//Ear. J. Med. Chem.— 1988.— Vol. 23.—P. 385

[6] Andreani A., Rambalbi M., Locatelli A., Isetta A. M.//Eur. J. Med. Chem.— 1991.— Vol. 26,— P. 335

[7] Chuev V. P., Lyaghina L. A., Kovalenko S. V.//Sibirian J. Chem.—1991.— Vol. 5.— P. 158—159

[8] Ebeid M. Y., Amin K. M., Hussein M. M.// Egypt. J. Pharm.— Sei.— 1987.— Vol. 28.— P. 183—191

[9] El-Morsy S. S., Fadda A. A., El-Hossi- ni M. S.//J. Ind. Chem. Soc.— 1988.— VoL 65.—P. 699—701

[10] Kaminski J. J.//J. Med. Chem.— 1989.— Vol. 32.—P. 1686

[11] Koelsch C. F.//J. Am. Chem. Soc.— 1950,—Vol. 72—. P. 2993—2995

[12] Mase T., Hidek A., Kemichi T.//J. Med. Chem.— 1986,—Vol. 29.—P. 386

[13] Rao V. R., Rao T. V. P.//Ind. J. Chem.— 1986.—Vol. 25B.— P. 413—415

[14] Vserabhadraiah U., Rao V. R.//d, Ind. Chem. Soc.— 1990 —Vol. 67, № 1.—P. 81—82

RIGHTS & PERMISSIONS

Eco-Vector