DOI: https://doi.org/10.24959/ophcj.19.174072

The study of the antimicrobial activity of the derivatives of 6-(1,2,4-oxadizol-3-yl)- and 6-(2-aminothiazol-4-yl)thieno[2,3-d]pyrimidin-4-ones by the double dilution method

S. V. Vlasov, S. M. Kovalenko, T. P. Osolodchenko, V. S. Vlasov

Abstract


Aim. To study profoundly the antimicrobial activity of the derivatives of 6-(1,2,4-oxadizol-3-yl)- and 6-(2-aminothiazol-4-yl)thieno[2,3-d]pyrimidin-4-ones by the double dilution method.
Results and discussion. For the derivatives of 6-heterylthieno[2,3-d]pyrimidines, namely the derivatives of 6-(1,2,4-oxadizol-3-yl)- and 6-(2-aminothiazol-4-yl)thieno[2,3-d]pyrimidin-4-ones selected after the prescreening by the agar well diffusion method, the further antimicrobial activity study using the double dilution method was performed. The minimal bacteriostatic and bactericidal concentrations were determined.
Experimental part. The synthesis of the target molecules was performed according to the methods previously developed. The antimicrobial activity was studied using the double-dilution method.
Conclusions. The derivatives of 5-methyl-6-(3-aryl-1,2,4-oxadizol-5-yl)thieno[2,3-d]pyrimidin-4(3H)-one with the free position 3 of the thieno[2,3-d]pyrimidine system showed the highest bactericidal activity in the concentration of 125 μg/mL against the test-strains of S. aureus, E. coli and B. subtilis.

Keywords


thiophene; pyrimidine; antibacterials

References


Vlasov, S. V., Kovalenko, S. M., Fedosov, A. I., Chernykh, V. P. (2011). Journal of Organic and Pharmaceutical Chemistry, 9 (35), 51–55.

Vlasov, S. V., Zaremba, O. V., Kovalenko, S. M., Fedosov, A. I., Chernykh, V. P. (2011). Journal of Organic and Pharmaceutical Chemistry, 9 (36), 24–30.

Vlasov, S. V., Kovalenko, S. M., Chernykh, V. P. (2013). Journal of Organic and Pharmaceutical Chemistry, 11 (42), 41–46.

Elzein, E., Kalla, R., Zablocki, J., Li, X., Perry, T., Kobayashi, T., Parkhill E. (2007). Pat. 2007/0208040 US, Int. Cl. A 61 K31/519, C 07 D498/02. A2A Adenosine receptor anatagonists.

Grinev, A. N., Kaplina, N. V. (1985). Transformations of 5-methyl-6-carbethoxy-3,4-dihydrothieno[2,3-d]pyrimidine for synthesis of 4-methoxy-, 4-alkylamino-, and other derivatives of thieno[2,3-d]pyrimidine. Chemistry of Heterocyclic Compounds, 21 (7), 767–770. https://doi.org/10.1007/bf00519143

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GOST Style Citations


1. Синтез нових 3-заміщених 1-алкіл-5-метил-6-(3-арил-1,2,4-оксадіазол-5-іл)тієно[2,3-d]піримідин-2,4(1Н,3Н)-діонів та їх антимікробна активність / С. В. Власов, С. М. Коваленко, А. І. Федосов, В. П. Черних // Журн. орган. та фармац. хімії. – 2011. – Т. 9, № 3 (35). – С. 51–55.

 

2. Синтез похідних 5-метилтієно[2,3-d]піримідин-4(3H)-ону із положенням 6 модифікованим 1,2,4- та 1,3,4-оксадіазолом, та їх біологічна активність / С. В. Власов, О. В. Заремба, С. М. Коваленко та ін. // Журн. орган. та фармац. хімії. – 2011. – Т. 9, № 4 (36). – С. 24–30.


3. Власов, С. В. Синтез та антимікробна дія 3-феніл-6-(2-аміно-1,3-тіазол-4-іл)-5-метилтієно[2,3-d]піримідин-2,4(1Н,3Н)-діонів / С. В. Власов, С. М. Коваленко, В. П. Черних // Журн. орган. та фармац. хімії. – 2013. – Т. 11, № 2 (42). – С. 41–46.


4. Пат. 2007/0208040 US, МПК A 61 K 31/519 (2006.01), C 07 D498/02 (2006.01). A2a Adenosine receptor anatagonists / Elzein E., Kalla R., Zablocki J., Li X., Perry T., Kobayashi T., Parkhill E. – № 11/681,378 ; заявл. 02.03.2007 ; опубл. 06.09.2007. – 33 p.


5. Grinev, A. N. Transformations of 5-methyl-6-carbethoxy-3,4-dihydrothieno[2,3-d]pyrimidine for synthesis of 4-methoxy-, 4-alkylamino-, and other derivatives of thieno[2,3-d]pyrimidine / A. N. Grinev, N. V. Kaplina // Chem. Heterocycl. Compd. – 1985. – Vol. 21, Issue 7. – P. 767–770. https://doi.org/10.1007/bf00519143


6. Coyle, M. B. Manual of Antimicrobial Susceptibility Testing. American Society for Microbiology / M. B. Coyle. – Washington : American Society of Microbiology, 2005. – 236 p.


7. Performance Standards for Antimicrobial Susceptibility Testing ; Twenty–Second Informational Supplement. Document M100-S22 // CLSI, Wayne, PA. – 2012. – Vol. 32, Issue 3.





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Abbreviated key title: J. Org. Pharm. Chem.

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