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SYNTHESIS AND TUBERCULOSTATIC ACTIVITY OF PYRROLYL AND PYRAZOLINYL PODANDS

О. В. Федорова, И. Г. Овчинникова, М. А. Кравченко, С. Н. Скорняков, Г. Л. Русинов, О. Н. Чупахин, В. Н. Чарушин
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Abstract


New podands containing pyrrole or pyrazoline fragments have been synthesized. A hypothesis was proposed that closure of the pyrrole ring in the presence of alumina nanoparticles may proceed through 1,4‑addition of nitroethane to the chalcone podand to give the Michael adduct rather than through an iminium intermediate usually observed in the reactions of α,β‑unsaturated ketones (chalcones) in the presence of Lewis acids. Moderate tuberculostatic activity was found for the starting chalcone podands. Much greater such activity was found upon subsequent modification of the chalcone fragment to give a five‑membered heterocycle. Pyrrole derivatives displayed greatest activity among the hetaryl podands obtained.

How to Cite
Fedorova, O. V.; Ovchinnikova, I. G.; Kravchenko, M. A.; Skornyakov, S. N.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. Chem. Heterocycl. Compd. 2014, 50, 946. [Khim. Geterotsikl. Soedin. 2014, 1027.]

For this article in the English edition see DOI 10.1007/s10593-014-1549-5


Keywords


pyrazolinyl podands; pyrrolyl podands; multicomponent reactions; tuberculostatic activity

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