The Synthesis and Antimicrobial Properties of New 2-(R-Phenylimino)-1,3-thiazoline Derivatives Containing the N-Methylpiperazine Moiety

dc.citation.epage156
dc.citation.issue2
dc.citation.spage150
dc.contributor.affiliationNational University of Pharmacy
dc.contributor.affiliationChernihiv National T.G. Shevchenko Pedagogical University
dc.contributor.affiliationNational Academy of Medical Sciences
dc.contributor.authorYeromina, Hanna
dc.contributor.authorDemchenko, Nataliya
dc.contributor.authorKiz, Olga
dc.contributor.authorIeromina, Zinaida
dc.contributor.authorDemchenko, Sergiy
dc.coverage.placenameЛьвів
dc.coverage.placenameLviv
dc.date.accessioned2020-03-02T12:28:12Z
dc.date.available2020-03-02T12:28:12Z
dc.date.created2019-02-28
dc.date.issued2019-02-28
dc.description.abstractНа 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.
dc.description.abstractNew 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.
dc.format.extent150-156
dc.format.pages7
dc.identifier.citationThe 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.
dc.identifier.citationenThe 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.
dc.identifier.urihttps://ena.lpnu.ua/handle/ntb/46470
dc.language.isoen
dc.publisherВидавництво Львівської політехніки
dc.publisherLviv Politechnic Publishing House
dc.relation.ispartofChemistry & Chemical Technology, 2 (13), 2019
dc.relation.references1. Pogrebova І., Kozlova І., Purіsh L., Sokolovs'kaM.:Naukovі Vіstі Nats. Tekhn. Unіv. Ukrainy “Kyivsky Polіtekhnіch. Institut”, 2015, 6, 115.
dc.relation.references2. Andreyuk К., Kozlova І., Kopteva Zh. et al.: Mіkrobna Korozіya Pіdzemnih Sporud. Naukova dumka, Kyiv 2005.
dc.relation.references3. Shiran J., Yahyazadeh A., Yamin B. et al.: Heterocycles, 2015, 91, 123. https://doi.org/10.3987/COM-14-13123
dc.relation.references4. Park I.-K., Lim C.-S., NamK.-D. et al.:Korean J. Pesticide Sci., 2006, 10, 149.
dc.relation.references5. LimJ.-S., HanM.-S., NamK.-D. et al.:Korean J. Pesticide Sci., 2009, 13, 63.
dc.relation.references6. Sondhi S., Singh N., Lahoti A. et al.: Bioorg. Med. Chem., 2005, 13, 4291. https://doi.org/10.1016/j.bmc.2005.04.017
dc.relation.references7. Sondhi S., Bhattacharjee G., Jameel R. et al.: Cent. Eur. J. Chem., 2004, 2, 1. https://doi.org/10.2478/BF02476181
dc.relation.references8. 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
dc.relation.references9. HearnM., Wang T., CynamonM.: J. Heterocyclic Chem., 2017, 54, 720. https://doi.org/10.1002/jhet.2551
dc.relation.references10. TahaM., Ismail N., JamilW. et al.:Med. Chem. Res., 2015, 24, 3166. https://doi.org/10.1007/s00044-015-1369-x
dc.relation.references11. 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
dc.relation.references12. Bae S., Hahn H.-G., NamK.-D.: J. Comb. Chem., 2005, 7, 7. https://doi.org/10.1021/cc049854w
dc.relation.references13. Bae S., Hahn H.-G., NamK.-D.: J. Comb. Chem., 2005, 7, 826. https://doi.org/10.1021/cc049811f
dc.relation.references14. Shin D., Lee J., Hahn H.-G.: Tetrahedron, 2010, 66, 5707. https://doi.org/10.1016/j.tet.2010.05.015
dc.relation.references15. Bramley S., Dupplin V., Goberdhan D., Meakins G.: J. Chem. Soc. Perkin Transact. 1, 1987, 1, 639. https://doi.org/10.1039/P19870000639
dc.relation.references16. Vogel A., Tatchell A., Furnis B. et al.:Vogel’s Textbook of Practical Organic Chemistry, 5th edn. Prentice Hall, Pearson 2005.
dc.relation.references17. Nath J., Ghosh H., Yella R., Patel B.: Eur. J. Org. Chem., 2009, 2009, 1849. https://doi.org/10.1002/ejoc.200801270
dc.relation.references18. Ghosh H.: Synlett, 2009, 17, 2882. https://doi.org/10.1055/s-0029-1217993
dc.relation.references19. Ghosh H., Yella R., Nath J., Patel B.: Eur. J. Org. Chem., 2008, 6189. https://doi.org/10.1002/ejoc.200800901
dc.relation.references20. 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
dc.relation.references21. Nath J., Ghosh H., Yella R., Patel B.: Eur. J. Org. Chem., 2009, 2009, 1849. https://doi.org/10.1002/ejoc.200801270
dc.relation.references22. Wong R., Dolman S.: J. Org. Chem., 2007, 72, 3969. https://doi.org/10.1021/jo070246n
dc.relation.references23. HollerM., Campo L., Brandelli A., Stefani V.: J. Photochem. Photobiol. A, 2002, 149, 217. https://doi.org/10.1016/S1010-6030(02)00008-4
dc.relation.references24. Wróblewska A., Mlostoń G.: Phosphorus Sulfur, 2013, 188, 509. https://doi.org/10.1080/10426507.2012.736897
dc.relation.references25. Demchenko S., Yeromina H., Perekhoda L. et al.: Pat. UA111015, Publ. Oct. 25, 2016.
dc.relation.references26. Demchenko S., Yeromina H., Perekhoda L. et al.: Pat. UA121484, Publ. Dec. 11, 2017.
dc.relation.references27. Yeromina H., Koshova O., Shcherbinina V. et al.: Pat. UA120509, Publ. Nov. 10, 2017.
dc.relation.references28. Yeromina H., Koshova O., Shcherbinina V. et al.: Pat. UA120847, Publ. Nov. 27, 2017.
dc.relation.references29. Perekhoda L., Yeromina H., Drapak I. et al.: SJMPS, 2017, 3, 55.
dc.relation.references30. ChoD., Parthasarathi R., Pimentel A. et al.: J. Org. Chem., 2010, 75, 6549. https://doi.org/10.1021/jo1012509
dc.relation.references31. Akbarzadeh A., Soleymani R., Taheri M., Karimi-Cheshmeh ali M.:Orient. J. Chem., 2012, 28, 153.
dc.relation.references32. Yurttaş L., Özkay Y., DuranM. et al.: Phosphorus Sulfur, 2016, 191, 1166. https://doi.org/10.1080/10426507.2016.1150277
dc.relation.references33. Yang Z., Huang N., Xu B. et al.:Molecules, 2016, 21, 232. https://doi.org/10.3390/molecules21030232
dc.relation.references34. Chen J., Liu D., Butt N. et al.: Angewandte Chemie Int. Edn., 2013, 52, 11632. https://doi.org/10.1002/anie.201306231
dc.relation.references35. Demchenko N., Kurmakova I., Tretyak O.:Microbiologia i Biotechnologia, 2013, 4, 90.
dc.relation.references36. Ehorov N.: Rukovodstvo k Praktycheskym Zaniatyiampo Microbyolohyy. Izd-voMHU, Мoskva 1983.
dc.relation.references37. Demchenko A., YanchenkoV., Kisly V., LozinskiiM.: Chem. Heterocycl. Compd., 2005, 41, 668. https://doi.org/10.1007/s10593-005-0200-x
dc.relation.references38. LudwigM., Stverka P.: Collect. Czech. Chem. Commun., 1996, 61, 1205. https://doi.org/10.1135/cccc19961205
dc.relation.referencesen1. Pogrebova I., Kozlova I., Purish L., Sokolovs'kaM.:Naukovi Visti Nats. Tekhn. Univ. Ukrainy "Kyivsky Politekhnich. Institut", 2015, 6, 115.
dc.relation.referencesen2. Andreyuk K., Kozlova I., Kopteva Zh. et al., Mikrobna Koroziya Pidzemnih Sporud. Naukova dumka, Kyiv 2005.
dc.relation.referencesen3. Shiran J., Yahyazadeh A., Yamin B. et al., Heterocycles, 2015, 91, 123. https://doi.org/10.3987/COM-14-13123
dc.relation.referencesen4. Park I.-K., Lim C.-S., NamK.-D. et al.:Korean J. Pesticide Sci., 2006, 10, 149.
dc.relation.referencesen5. LimJ.-S., HanM.-S., NamK.-D. et al.:Korean J. Pesticide Sci., 2009, 13, 63.
dc.relation.referencesen6. Sondhi S., Singh N., Lahoti A. et al., Bioorg. Med. Chem., 2005, 13, 4291. https://doi.org/10.1016/j.bmc.2005.04.017
dc.relation.referencesen7. Sondhi S., Bhattacharjee G., Jameel R. et al., Cent. Eur. J. Chem., 2004, 2, 1. https://doi.org/10.2478/BF02476181
dc.relation.referencesen8. 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
dc.relation.referencesen9. HearnM., Wang T., CynamonM., J. Heterocyclic Chem., 2017, 54, 720. https://doi.org/10.1002/jhet.2551
dc.relation.referencesen10. TahaM., Ismail N., JamilW. et al.:Med. Chem. Res., 2015, 24, 3166. https://doi.org/10.1007/s00044-015-1369-x
dc.relation.referencesen11. 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
dc.relation.referencesen12. Bae S., Hahn H.-G., NamK.-D., J. Comb. Chem., 2005, 7, 7. https://doi.org/10.1021/cc049854w
dc.relation.referencesen13. Bae S., Hahn H.-G., NamK.-D., J. Comb. Chem., 2005, 7, 826. https://doi.org/10.1021/cc049811f
dc.relation.referencesen14. Shin D., Lee J., Hahn H.-G., Tetrahedron, 2010, 66, 5707. https://doi.org/10.1016/j.tet.2010.05.015
dc.relation.referencesen15. Bramley S., Dupplin V., Goberdhan D., Meakins G., J. Chem. Soc. Perkin Transact. 1, 1987, 1, 639. https://doi.org/10.1039/P19870000639
dc.relation.referencesen16. Vogel A., Tatchell A., Furnis B. et al.:Vogel’s Textbook of Practical Organic Chemistry, 5th edn. Prentice Hall, Pearson 2005.
dc.relation.referencesen17. Nath J., Ghosh H., Yella R., Patel B., Eur. J. Org. Chem., 2009, 2009, 1849. https://doi.org/10.1002/ejoc.200801270
dc.relation.referencesen18. Ghosh H., Synlett, 2009, 17, 2882. https://doi.org/10.1055/s-0029-1217993
dc.relation.referencesen19. Ghosh H., Yella R., Nath J., Patel B., Eur. J. Org. Chem., 2008, 6189. https://doi.org/10.1002/ejoc.200800901
dc.relation.referencesen20. 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
dc.relation.referencesen21. Nath J., Ghosh H., Yella R., Patel B., Eur. J. Org. Chem., 2009, 2009, 1849. https://doi.org/10.1002/ejoc.200801270
dc.relation.referencesen22. Wong R., Dolman S., J. Org. Chem., 2007, 72, 3969. https://doi.org/10.1021/jo070246n
dc.relation.referencesen23. HollerM., Campo L., Brandelli A., Stefani V., J. Photochem. Photobiol. A, 2002, 149, 217. https://doi.org/10.1016/S1010-6030(02)00008-4
dc.relation.referencesen24. Wróblewska A., Mlostoń G., Phosphorus Sulfur, 2013, 188, 509. https://doi.org/10.1080/10426507.2012.736897
dc.relation.referencesen25. Demchenko S., Yeromina H., Perekhoda L. et al., Pat. UA111015, Publ. Oct. 25, 2016.
dc.relation.referencesen26. Demchenko S., Yeromina H., Perekhoda L. et al., Pat. UA121484, Publ. Dec. 11, 2017.
dc.relation.referencesen27. Yeromina H., Koshova O., Shcherbinina V. et al., Pat. UA120509, Publ. Nov. 10, 2017.
dc.relation.referencesen28. Yeromina H., Koshova O., Shcherbinina V. et al., Pat. UA120847, Publ. Nov. 27, 2017.
dc.relation.referencesen29. Perekhoda L., Yeromina H., Drapak I. et al., SJMPS, 2017, 3, 55.
dc.relation.referencesen30. ChoD., Parthasarathi R., Pimentel A. et al., J. Org. Chem., 2010, 75, 6549. https://doi.org/10.1021/jo1012509
dc.relation.referencesen31. Akbarzadeh A., Soleymani R., Taheri M., Karimi-Cheshmeh ali M.:Orient. J. Chem., 2012, 28, 153.
dc.relation.referencesen32. Yurttaş L., Özkay Y., DuranM. et al., Phosphorus Sulfur, 2016, 191, 1166. https://doi.org/10.1080/10426507.2016.1150277
dc.relation.referencesen33. Yang Z., Huang N., Xu B. et al.:Molecules, 2016, 21, 232. https://doi.org/10.3390/molecules21030232
dc.relation.referencesen34. Chen J., Liu D., Butt N. et al., Angewandte Chemie Int. Edn., 2013, 52, 11632. https://doi.org/10.1002/anie.201306231
dc.relation.referencesen35. Demchenko N., Kurmakova I., Tretyak O.:Microbiologia i Biotechnologia, 2013, 4, 90.
dc.relation.referencesen36. Ehorov N., Rukovodstvo k Praktycheskym Zaniatyiampo Microbyolohyy. Izd-voMHU, Moskva 1983.
dc.relation.referencesen37. Demchenko A., YanchenkoV., Kisly V., LozinskiiM., Chem. Heterocycl. Compd., 2005, 41, 668. https://doi.org/10.1007/s10593-005-0200-x
dc.relation.referencesen38. LudwigM., Stverka P., Collect. Czech. Chem. Commun., 1996, 61, 1205. https://doi.org/10.1135/cccc19961205
dc.relation.urihttps://doi.org/10.3987/COM-14-13123
dc.relation.urihttps://doi.org/10.1016/j.bmc.2005.04.017
dc.relation.urihttps://doi.org/10.2478/BF02476181
dc.relation.urihttps://doi.org/10.1016/j.bmcl.2004.08.035
dc.relation.urihttps://doi.org/10.1002/jhet.2551
dc.relation.urihttps://doi.org/10.1007/s00044-015-1369-x
dc.relation.urihttps://doi.org/10.1016/j.ejmech.2008.12.005
dc.relation.urihttps://doi.org/10.1021/cc049854w
dc.relation.urihttps://doi.org/10.1021/cc049811f
dc.relation.urihttps://doi.org/10.1016/j.tet.2010.05.015
dc.relation.urihttps://doi.org/10.1039/P19870000639
dc.relation.urihttps://doi.org/10.1002/ejoc.200801270
dc.relation.urihttps://doi.org/10.1055/s-0029-1217993
dc.relation.urihttps://doi.org/10.1002/ejoc.200800901
dc.relation.urihttps://doi.org/10.1016/j.ejmech.2010.08.034
dc.relation.urihttps://doi.org/10.1021/jo070246n
dc.relation.urihttps://doi.org/10.1016/S1010-6030(02)00008-4
dc.relation.urihttps://doi.org/10.1080/10426507.2012.736897
dc.relation.urihttps://doi.org/10.1021/jo1012509
dc.relation.urihttps://doi.org/10.1080/10426507.2016.1150277
dc.relation.urihttps://doi.org/10.3390/molecules21030232
dc.relation.urihttps://doi.org/10.1002/anie.201306231
dc.relation.urihttps://doi.org/10.1007/s10593-005-0200-x
dc.relation.urihttps://doi.org/10.1135/cccc19961205
dc.rights.holder© Національний університет „Львівська політехніка“, 2019
dc.rights.holder© Yeromina H., Demchenko N., Kiz O., Ieromina Z., Demchenko S., 2019
dc.subject2-(R-феніліміно)-1
dc.subject3-тіазолін
dc.subjectN-метил-піперазин
dc.subjectсинтез Ганча
dc.subjectантимікробна активність
dc.subjectсульфат-відновлювальні бактерії
dc.subject2-(R-phenylimino)-1
dc.subject3-thiazoline
dc.subjectN-methylpiperazine
dc.subjectHantzsch synthesis
dc.subjectantimicrobial activity
dc.subjectsulfate-reducing bacteria
dc.titleThe Synthesis and Antimicrobial Properties of New 2-(R-Phenylimino)-1,3-thiazoline Derivatives Containing the N-Methylpiperazine Moiety
dc.title.alternativeСинтез та властивості нових похідних 2-(R-феніліміно)-1,3-тіазоліну, що містять фрагмент N-метилпіперазину
dc.typeArticle

Files

Original bundle

Now showing 1 - 2 of 2
Thumbnail Image
Name:
2019v13n2_Yeromina_H-The_Synthesis_and_Antimicrobial_150-156.pdf
Size:
532.76 KB
Format:
Adobe Portable Document Format
Thumbnail Image
Name:
2019v13n2_Yeromina_H-The_Synthesis_and_Antimicrobial_150-156__COVER.png
Size:
518.84 KB
Format:
Portable Network Graphics

License bundle

Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
3 KB
Format:
Plain Text
Description: