Screening of the antiviral activity in the range of C5 and N3 substituted 4-thiazolidinone derivatives

D. V. Kaminskyy

Abstract


Prospects for the search of antiviral agents among 4-thiazolidinone derivatives, as well as the optimal directions of the main core structure optimization – namely C5 and N3, have been described. As the result of the screening performed (within the Antimicrobial Acquisition and Coordinating Facility programme), the values of the antiviral activity of the target 5-substituted-4-thiazolidinones with the carboxylic group (or its derivatives) in the N3 residue on relation to a wide range of the viral panels have been determined. The active compounds, which can be regarded as promising structures in the anti-flu agent design, have been identified, as well as 3-{5-[2-chloro-3-(4-nitrophenyl)-allylidene]-4-oxo-2-thioxothiazolidine-3-yl}-propionic (1) and –succinic acids (3) have been identified has hit-compounds with a marked anti-VZV activity (SI values – 27 and 38, respectively).


Keywords


4-thiazolidinones; screening; antiviral activity

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References


Tripathi A. C., Gupta S. J., Fatima, G. N., Sonar P. K., Verma A., Saraf S. K. European Journal of Medicinal Chemistry, 2014, Vol. 72, pp.52-77. doi 10.1016/j.ejmech.2013.11.017.

Lesyk R. B., Zimenkovsky B. S. Current Organic Chemistry, 2004, Vol. 8, No.16, pp.1547-1577. doi:10.2174/1385272043369773.

Lesyk R. B., Zimenkovsky B. S., Kaminskyy D. V., Kryshchyshyn A. P., Havryluk D. Ya., Atamanyuk D. V., Subtel’na I. Yu., Khyluk D. V. Biopolymer and Cell, 2011, Vol. 27, No.2, pp.107-117. doi: 10.7124/bc.000089.

Zhang Y., Wang S., Wu S., Zhu S., Dong G., Miao Z., Yao J., Zhang W., Sheng C., Wang W. ACS Combinatorial Science, 2013, Vol. 15, No.6, pp.298-308. doi: 10.1021/co400022r.

Tomašic T., Mašic L. Expert Opinion on Drug Discovery, 2012, Vol. 7. No.7, pp.549-560. doi: 10.1517/17460441.2012.688743.

Kaminskyy D. V., Lesyk R. B. Biopolymer and Cell, 2010, Vol. 26, No.2, pp.136-145. doi: 10.7124/bc.000150.

Kaminskyy D., Zimenkovsky B., Lesyk R. European Journal of Medicinal Chemistry, 2009, Vol. 44, No.9. pp.3627-3636. doi: 10.1016/j.ejmech.2009.02.023.

Bhat B. A., Ponnala S., Sahu D. P. Tiwari P., Tripathi B. K., Srivastava A. K. Bioorganic and Medicinal Chemistry, 2004, Vol. 12, No.22, pp.5857-5864. doi: 10.1016/j.bmc.2004.08.031.

Volynets G. P., Bdzhola V. G., Golub A. G., Synyugin A. R., Chekanov M. A., Kukharenko O. P., Yarmoluk S. M. European Journal of Medicinal Chemistry, 2013, Vol.61, pp.104-115. doi: 10.1016/j.ejmech.2012.09.022.

Baell J. B., Holloway G. A. Journal of Medicinal Chemistry, 2010, Vol. 53, No.7, pp.2719-2740. doi: 10.1021/jm901137j.

Mendgen T., Steuer C., Klein C. D. Journal of Medicinal Chemistry, 2012, Vol. 55, No.2, pp.743-753. doi 10.1021/jm201243p.

Sing W. T., Lee C. L., Yeo S. L., Lim S. P., Sim M. Biorganic and Medicinal Chemistry Letter, 2001, Vol. 11, No.2, pp.91-94. doi: 10.1016/S0960-894X(00)00610-7.

Vermehren J., Sarrazin C. Clinical Microbiology and Infection, 2011, Vol. 17, No.2, pp.122-134. doi: 10.1111/j.1469-0691.2010.03430.x.

Kucukguzel I., Satılmıs G., Gurukumar K. R., Basu A., Tatar E., Nichols D. B., Talele T. T., Kaushik-Basu N. European Journal of Medicinal Chemistry, 2013, Vol. 69, pp.931-941. doi: 10.1016/j.ejmech.2013.08.043

Barreca M. L., Chimirri A., De Clercq E., De Luca L., Monforte A. M., Monforte P., Rao A., Zappala M. Il Farmaco, 2003, Vol. 58, No.3, pp.259-263. doi: 10.1016/S0014-827X(03)00024-7.

Maga G., Falchi F., Garbelli A., Belfiore A., Witvrouw M., Manetti F., Botta M. Journal of Medicinal Chemistry, 2008, Vol. 51, No.21, pp.6635-6638. doi: 10.1021/jm8008844.

Dayam R., Gundla R., Al-Mawsawi L. Q., Neamati N. Medicinal Research Reviews, 2008, Vol. 28, No.1, pp.118-154. doi: 10.1002/med.20116.

Havrylyuk D., Zimenkovsky B., Vasylenko O., Lesyk R. Journal of Heterocyclic Chemistry, 2013, Vol. 50, No.S1, pp.E55-E62. doi: 10.1002/jhet.1056.

Havrylyuk D., Khyrkov S., Atamanyuk V., Zimenkovsky B., Lesyk R. Aktualni Pytannia Farmacevtychnoi Nauky i Praktyky – Current Issues in Pharmacy and Medicine: Science and Practice, 2012, Vol. 10, No.3, pp.32-41. (in Ukrainian). http://pharmed.zsmu.edu.ua/issue/viewIssue/1480/236.

Gavrylyuk D. Ya., Zimenkovsky B. S., Vasylenko O. M., Lesyk R. B. Zhurnal Organichnoi i Farmacevtychnoi Chimii – Journal of Organic and Pharmaceutical Chemistry, 2009, Vol. 7, No.1(25), pp.42-47. (in Ukrainian). http://ru.nuph.edu.ua/files/2012/03/%D0%96%D0%9E%D0%A4%D0%A5-1-2009-42-47.pdf.

Kaminskyy D. V., Roman O. M., Atamanyuk D. V., Lesyk R. B. Zhurnal Organichnoi i Farmacevtychnoi Chimii – Journal of Organic and Pharmaceutical Chemistry, 2006, Vol. 4, No.1(13), pp.41-48. (in Ukrainian). http://dspace.nbuv.gov.ua/bitstream/handle/123456789/42099/05-Kaminsky. pdf?sequence=1.

Kaminskyy D. V., Lesyk R. B. Farmacevtychyy Zhurnal – Pharmaceutical Journal, 2008, No.3, pp.70-78. (in Ukarinian).

Zimenkovskii B. S., Kutsyk R. V., Lesyk R. B., Matyichuk V. S., Obushak N. D., Klyufinska T. I. Pharmaceutical Chemistry Journal, 2006, Vol. 40, No.6, pp.303-306. doi: 10.1007/s11094-006-0115-6.

Severson W. E., Shindo N., Sosa M., Fletcher T., White E. L., Ananthan S., Jonsson C. B. Journal of Biomolecular Screening, 2007, Vol. 12, No.1, pp.33-40. doi: 10.1177/1087057106296688.

Cotarelo M., Catalán P., Sánchez-Carrillo C., Menasalvas A., Cercenado E., Tenorio A., Bouza E. Journal of Antimicrobial Chemotherapy, 1999, Vol. 44, No.5, pp.705-708. doi: 10.1093/jac/44.5.705.

Krieger N., Lohmann V., Bartenschlager R. Journal of Virology, 2001, Vol. 75, No.10, pp.4614-4624. doi: 10.1128/JVI.75.10.4614-4624.2001.

Korba B. E., Gerin J. L. Antiviral Research, 1992, Vol. 19, No.1, pp.55-70. doi: 10.1016/0166-3542(92)90056-B.

Sidwell R. W., Huffman, J. H. Applied Microbiology, 1971, Vol. 22, No.5, pp. 797-801. http://aem.asm.org/content/22/5/797.full.pdf+html


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DOI: https://doi.org/10.24959/ophcj.15.819

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)