https://oldena.lpnu.ua/handle/ntb/46470
Title: | The Synthesis and Antimicrobial Properties of New 2-(R-Phenylimino)-1,3-thiazoline Derivatives Containing the N-Methylpiperazine Moiety |
Other Titles: | Синтез та властивості нових похідних 2-(R-феніліміно)-1,3-тіазоліну, що містять фрагмент N-метилпіперазину |
Authors: | Yeromina, Hanna Demchenko, Nataliya Kiz, Olga Ieromina, Zinaida Demchenko, Sergiy |
Affiliation: | National University of Pharmacy Chernihiv National T.G. Shevchenko Pedagogical University National Academy of Medical Sciences |
Bibliographic description (Ukraine): | The Synthesis and Antimicrobial Properties of New 2-(R-Phenylimino)-1,3-thiazoline Derivatives Containing the N-Methylpiperazine Moiety / Hanna Yeromina, Nataliya Demchenko, Olga Kiz, Zinaida Ieromina, Sergiy Demchenko // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2019. — Vol 13. — No 2. — P. 150–156. |
Bibliographic description (International): | The Synthesis and Antimicrobial Properties of New 2-(R-Phenylimino)-1,3-thiazoline Derivatives Containing the N-Methylpiperazine Moiety / Hanna Yeromina, Nataliya Demchenko, Olga Kiz, Zinaida Ieromina, Sergiy Demchenko // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2019. — Vol 13. — No 2. — P. 150–156. |
Is part of: | Chemistry & Chemical Technology, 2 (13), 2019 |
Issue: | 2 |
Issue Date: | 28-Feb-2019 |
Publisher: | Видавництво Львівської політехніки Lviv Politechnic Publishing House |
Place of the edition/event: | Львів Lviv |
Keywords: | 2-(R-феніліміно)-1 3-тіазолін N-метил-піперазин синтез Ганча антимікробна активність сульфат-відновлювальні бактерії 2-(R-phenylimino)-1 3-thiazoline N-methylpiperazine Hantzsch synthesis antimicrobial activity sulfate-reducing bacteria |
Number of pages: | 7 |
Page range: | 150-156 |
Start page: | 150 |
End page: | 156 |
Abstract: | На основі несиметричних тіосечовин синте-
зовані нові похідні N-(R`-феніл)-3-(4-метил-1-піперазиніл)-1,3-
тіазол-2(3H)-іміну за реакцією Ганча. Структуру цільових
компонентів підтверджено елементим аналізом та ЯМР
спектроскопією. Досліджено антимікробну активність похід-
них 1,3-тіазоліну з N-метилпіперазиновим фрагментом щодо
сульфатвідновлювальних бактерій штаму Desulfovibrio sp. М
4.1. Встановлено, що сполуки з галогензаміщеним та незаміще-
ним фенільним фрагментом в 4-му положенні тіазолінового
циклу виявляють виразну протимікробну активність. New derivatives of N-(R-phenyl)-3-(4-methyl- 1-piperazinyl)-1,3-thiazole-2(3H)- imine with the medium to high yields were synthesized by the Hantzsch reaction in the ethanol medium. The structure of target compounds was confirmed by elemental analysis and NMR spectroscopy. The antimicrobial activity of 1,3-thiazoline derivatives with the N-methylpiperazine moiety against sulfate-reducing bacteria of Desulfovibrio sp. М.4.1 strain was studied. It was found that substances containing the halo- and unsubstituted phenyl fragment in the position 4 of the thiazoline cycle showed the potent antimicrobial activity. |
URI: | https://ena.lpnu.ua/handle/ntb/46470 |
Copyright owner: | © Національний університет „Львівська політехніка“, 2019 © Yeromina H., Demchenko N., Kiz O., Ieromina Z., Demchenko S., 2019 |
URL for reference material: | https://doi.org/10.3987/COM-14-13123 https://doi.org/10.1016/j.bmc.2005.04.017 https://doi.org/10.2478/BF02476181 https://doi.org/10.1016/j.bmcl.2004.08.035 https://doi.org/10.1002/jhet.2551 https://doi.org/10.1007/s00044-015-1369-x https://doi.org/10.1016/j.ejmech.2008.12.005 https://doi.org/10.1021/cc049854w https://doi.org/10.1021/cc049811f https://doi.org/10.1016/j.tet.2010.05.015 https://doi.org/10.1039/P19870000639 https://doi.org/10.1002/ejoc.200801270 https://doi.org/10.1055/s-0029-1217993 https://doi.org/10.1002/ejoc.200800901 https://doi.org/10.1016/j.ejmech.2010.08.034 https://doi.org/10.1021/jo070246n https://doi.org/10.1016/S1010-6030(02)00008-4 https://doi.org/10.1080/10426507.2012.736897 https://doi.org/10.1021/jo1012509 https://doi.org/10.1080/10426507.2016.1150277 https://doi.org/10.3390/molecules21030232 https://doi.org/10.1002/anie.201306231 https://doi.org/10.1007/s10593-005-0200-x https://doi.org/10.1135/cccc19961205 |
References (Ukraine): | 1. Pogrebova І., Kozlova І., Purіsh L., Sokolovs'kaM.:Naukovі Vіstі Nats. Tekhn. Unіv. Ukrainy “Kyivsky Polіtekhnіch. Institut”, 2015, 6, 115. 2. Andreyuk К., Kozlova І., Kopteva Zh. et al.: Mіkrobna Korozіya Pіdzemnih Sporud. Naukova dumka, Kyiv 2005. 3. Shiran J., Yahyazadeh A., Yamin B. et al.: Heterocycles, 2015, 91, 123. https://doi.org/10.3987/COM-14-13123 4. Park I.-K., Lim C.-S., NamK.-D. et al.:Korean J. Pesticide Sci., 2006, 10, 149. 5. LimJ.-S., HanM.-S., NamK.-D. et al.:Korean J. Pesticide Sci., 2009, 13, 63. 6. Sondhi S., Singh N., Lahoti A. et al.: Bioorg. Med. Chem., 2005, 13, 4291. https://doi.org/10.1016/j.bmc.2005.04.017 7. Sondhi S., Bhattacharjee G., Jameel R. et al.: Cent. Eur. J. Chem., 2004, 2, 1. https://doi.org/10.2478/BF02476181 8. Terzioglu N., van Rijn R., Bakker R. et al.: Bioorg. Med. Chem. Lett., 2004, 14, 5251. https://doi.org/10.1016/j.bmcl.2004.08.035 9. HearnM., Wang T., CynamonM.: J. Heterocyclic Chem., 2017, 54, 720. https://doi.org/10.1002/jhet.2551 10. TahaM., Ismail N., JamilW. et al.:Med. Chem. Res., 2015, 24, 3166. https://doi.org/10.1007/s00044-015-1369-x 11. Demirbasa A., Sahin D., Demirbas N., Karaoglu S.: Eur. J.Med. Chem., 2009, 44, 2896. https://doi.org/10.1016/j.ejmech.2008.12.005 12. Bae S., Hahn H.-G., NamK.-D.: J. Comb. Chem., 2005, 7, 7. https://doi.org/10.1021/cc049854w 13. Bae S., Hahn H.-G., NamK.-D.: J. Comb. Chem., 2005, 7, 826. https://doi.org/10.1021/cc049811f 14. Shin D., Lee J., Hahn H.-G.: Tetrahedron, 2010, 66, 5707. https://doi.org/10.1016/j.tet.2010.05.015 15. Bramley S., Dupplin V., Goberdhan D., Meakins G.: J. Chem. Soc. Perkin Transact. 1, 1987, 1, 639. https://doi.org/10.1039/P19870000639 16. Vogel A., Tatchell A., Furnis B. et al.:Vogel’s Textbook of Practical Organic Chemistry, 5th edn. Prentice Hall, Pearson 2005. 17. Nath J., Ghosh H., Yella R., Patel B.: Eur. J. Org. Chem., 2009, 2009, 1849. https://doi.org/10.1002/ejoc.200801270 18. Ghosh H.: Synlett, 2009, 17, 2882. https://doi.org/10.1055/s-0029-1217993 19. Ghosh H., Yella R., Nath J., Patel B.: Eur. J. Org. Chem., 2008, 6189. https://doi.org/10.1002/ejoc.200800901 20. Khan I., Ali S., Hameed S. et al.: Eur. J. Med. Chem., 2010, 45, 5200. https://doi.org/10.1016/j.ejmech.2010.08.034 21. Nath J., Ghosh H., Yella R., Patel B.: Eur. J. Org. Chem., 2009, 2009, 1849. https://doi.org/10.1002/ejoc.200801270 22. Wong R., Dolman S.: J. Org. Chem., 2007, 72, 3969. https://doi.org/10.1021/jo070246n 23. HollerM., Campo L., Brandelli A., Stefani V.: J. Photochem. Photobiol. A, 2002, 149, 217. https://doi.org/10.1016/S1010-6030(02)00008-4 24. Wróblewska A., Mlostoń G.: Phosphorus Sulfur, 2013, 188, 509. https://doi.org/10.1080/10426507.2012.736897 25. Demchenko S., Yeromina H., Perekhoda L. et al.: Pat. UA111015, Publ. Oct. 25, 2016. 26. Demchenko S., Yeromina H., Perekhoda L. et al.: Pat. UA121484, Publ. Dec. 11, 2017. 27. Yeromina H., Koshova O., Shcherbinina V. et al.: Pat. UA120509, Publ. Nov. 10, 2017. 28. Yeromina H., Koshova O., Shcherbinina V. et al.: Pat. UA120847, Publ. Nov. 27, 2017. 29. Perekhoda L., Yeromina H., Drapak I. et al.: SJMPS, 2017, 3, 55. 30. ChoD., Parthasarathi R., Pimentel A. et al.: J. Org. Chem., 2010, 75, 6549. https://doi.org/10.1021/jo1012509 31. Akbarzadeh A., Soleymani R., Taheri M., Karimi-Cheshmeh ali M.:Orient. J. Chem., 2012, 28, 153. 32. Yurttaş L., Özkay Y., DuranM. et al.: Phosphorus Sulfur, 2016, 191, 1166. https://doi.org/10.1080/10426507.2016.1150277 33. Yang Z., Huang N., Xu B. et al.:Molecules, 2016, 21, 232. https://doi.org/10.3390/molecules21030232 34. Chen J., Liu D., Butt N. et al.: Angewandte Chemie Int. Edn., 2013, 52, 11632. https://doi.org/10.1002/anie.201306231 35. Demchenko N., Kurmakova I., Tretyak O.:Microbiologia i Biotechnologia, 2013, 4, 90. 36. Ehorov N.: Rukovodstvo k Praktycheskym Zaniatyiampo Microbyolohyy. Izd-voMHU, Мoskva 1983. 37. Demchenko A., YanchenkoV., Kisly V., LozinskiiM.: Chem. Heterocycl. Compd., 2005, 41, 668. https://doi.org/10.1007/s10593-005-0200-x 38. LudwigM., Stverka P.: Collect. Czech. Chem. Commun., 1996, 61, 1205. https://doi.org/10.1135/cccc19961205 |
References (International): | 1. Pogrebova I., Kozlova I., Purish L., Sokolovs'kaM.:Naukovi Visti Nats. Tekhn. Univ. Ukrainy "Kyivsky Politekhnich. Institut", 2015, 6, 115. 2. Andreyuk K., Kozlova I., Kopteva Zh. et al., Mikrobna Koroziya Pidzemnih Sporud. Naukova dumka, Kyiv 2005. 3. Shiran J., Yahyazadeh A., Yamin B. et al., Heterocycles, 2015, 91, 123. https://doi.org/10.3987/COM-14-13123 4. Park I.-K., Lim C.-S., NamK.-D. et al.:Korean J. Pesticide Sci., 2006, 10, 149. 5. LimJ.-S., HanM.-S., NamK.-D. et al.:Korean J. Pesticide Sci., 2009, 13, 63. 6. Sondhi S., Singh N., Lahoti A. et al., Bioorg. Med. Chem., 2005, 13, 4291. https://doi.org/10.1016/j.bmc.2005.04.017 7. Sondhi S., Bhattacharjee G., Jameel R. et al., Cent. Eur. J. Chem., 2004, 2, 1. https://doi.org/10.2478/BF02476181 8. Terzioglu N., van Rijn R., Bakker R. et al., Bioorg. Med. Chem. Lett., 2004, 14, 5251. https://doi.org/10.1016/j.bmcl.2004.08.035 9. HearnM., Wang T., CynamonM., J. Heterocyclic Chem., 2017, 54, 720. https://doi.org/10.1002/jhet.2551 10. TahaM., Ismail N., JamilW. et al.:Med. Chem. Res., 2015, 24, 3166. https://doi.org/10.1007/s00044-015-1369-x 11. Demirbasa A., Sahin D., Demirbas N., Karaoglu S., Eur. J.Med. Chem., 2009, 44, 2896. https://doi.org/10.1016/j.ejmech.2008.12.005 12. Bae S., Hahn H.-G., NamK.-D., J. Comb. Chem., 2005, 7, 7. https://doi.org/10.1021/cc049854w 13. Bae S., Hahn H.-G., NamK.-D., J. Comb. Chem., 2005, 7, 826. https://doi.org/10.1021/cc049811f 14. Shin D., Lee J., Hahn H.-G., Tetrahedron, 2010, 66, 5707. https://doi.org/10.1016/j.tet.2010.05.015 15. Bramley S., Dupplin V., Goberdhan D., Meakins G., J. Chem. Soc. Perkin Transact. 1, 1987, 1, 639. https://doi.org/10.1039/P19870000639 16. Vogel A., Tatchell A., Furnis B. et al.:Vogel’s Textbook of Practical Organic Chemistry, 5th edn. Prentice Hall, Pearson 2005. 17. Nath J., Ghosh H., Yella R., Patel B., Eur. J. Org. Chem., 2009, 2009, 1849. https://doi.org/10.1002/ejoc.200801270 18. Ghosh H., Synlett, 2009, 17, 2882. https://doi.org/10.1055/s-0029-1217993 19. Ghosh H., Yella R., Nath J., Patel B., Eur. J. Org. Chem., 2008, 6189. https://doi.org/10.1002/ejoc.200800901 20. Khan I., Ali S., Hameed S. et al., Eur. J. Med. Chem., 2010, 45, 5200. https://doi.org/10.1016/j.ejmech.2010.08.034 21. Nath J., Ghosh H., Yella R., Patel B., Eur. J. Org. Chem., 2009, 2009, 1849. https://doi.org/10.1002/ejoc.200801270 22. Wong R., Dolman S., J. Org. Chem., 2007, 72, 3969. https://doi.org/10.1021/jo070246n 23. HollerM., Campo L., Brandelli A., Stefani V., J. Photochem. Photobiol. A, 2002, 149, 217. https://doi.org/10.1016/S1010-6030(02)00008-4 24. Wróblewska A., Mlostoń G., Phosphorus Sulfur, 2013, 188, 509. https://doi.org/10.1080/10426507.2012.736897 25. Demchenko S., Yeromina H., Perekhoda L. et al., Pat. UA111015, Publ. Oct. 25, 2016. 26. Demchenko S., Yeromina H., Perekhoda L. et al., Pat. UA121484, Publ. Dec. 11, 2017. 27. Yeromina H., Koshova O., Shcherbinina V. et al., Pat. UA120509, Publ. Nov. 10, 2017. 28. Yeromina H., Koshova O., Shcherbinina V. et al., Pat. UA120847, Publ. Nov. 27, 2017. 29. Perekhoda L., Yeromina H., Drapak I. et al., SJMPS, 2017, 3, 55. 30. ChoD., Parthasarathi R., Pimentel A. et al., J. Org. Chem., 2010, 75, 6549. https://doi.org/10.1021/jo1012509 31. Akbarzadeh A., Soleymani R., Taheri M., Karimi-Cheshmeh ali M.:Orient. J. Chem., 2012, 28, 153. 32. Yurttaş L., Özkay Y., DuranM. et al., Phosphorus Sulfur, 2016, 191, 1166. https://doi.org/10.1080/10426507.2016.1150277 33. Yang Z., Huang N., Xu B. et al.:Molecules, 2016, 21, 232. https://doi.org/10.3390/molecules21030232 34. Chen J., Liu D., Butt N. et al., Angewandte Chemie Int. Edn., 2013, 52, 11632. https://doi.org/10.1002/anie.201306231 35. Demchenko N., Kurmakova I., Tretyak O.:Microbiologia i Biotechnologia, 2013, 4, 90. 36. Ehorov N., Rukovodstvo k Praktycheskym Zaniatyiampo Microbyolohyy. Izd-voMHU, Moskva 1983. 37. Demchenko A., YanchenkoV., Kisly V., LozinskiiM., Chem. Heterocycl. Compd., 2005, 41, 668. https://doi.org/10.1007/s10593-005-0200-x 38. LudwigM., Stverka P., Collect. Czech. Chem. Commun., 1996, 61, 1205. https://doi.org/10.1135/cccc19961205 |
Content type: | Article |
Appears in Collections: | Chemistry & Chemical Technology. – 2019. – Vol. 13, No. 2 |
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