Skip to main content
SpringerLink
Log in

Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Condensation of ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate with various aromatic amines and with 5-amino-3-(4-bromo- phenyl(tolyl))-1H-pyrazole in absolute boiling ethanol afforded new azomethines as Schiff bases. The structure and E-configuration of the azomethine fragment were detected by the methods of 1H NMR spectroscopy and X-ray analysis. Reaction of these compounds with thioglycolic acid in toluene, DMF, or AcOH at reflux with or without the addition of ZnCl2 as well as under microwave irradiation had an unusual pathway leading to the formation of ethyl 3,5-dimethyl-4-(5-oxo-1,3-oxathiolan-2-yl)-1H-pyrrole-2-carboxylate exclusively. The obtained azomethines were found to be effective only against Gram positive bacteria, whereas ethyl 4-{(E)-[(4-chlorophenyl)imino]- methyl}-3,5-dimethyl-1H-pyrrole-2-carboxylate exhibited the highest antibacterial activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1.
Scheme 2.
Scheme 3.
Scheme 4.
Figure 1.

Similar content being viewed by others

References

  1. (a) Coates, A.; Hu, Y.; Bax, R.; Page, C. Nat. Rev. Drug Discovery 2002, 1, 895. (b) Carlet, J.; Jarlier, V.; Harbarth, S.; Voss, A.; Goossens, H.; Pittet, D. Antimicrob. Resist. Infect. Control 2012, 1, 11. (c) Rahman, H.; Austin, B.; Mitchell, W. J.; Morris, P. C.; Jamieson, D. J.; Adams, D. R.; Spragg, A. M.; Schweizer, M. Mar. Drugs 2010, 8, 498. (d) Li, R. Med. Res. Rev. 2016, 36, 169.

  2. (a) Sathe, B. S.; Jaychandran, E.; Jagtap, V. A.; Sreenivasa, G. M. Int. J. Pharm. Res. Dev. 2011, 3, 164. (b) Sondhi, S. M.; Singh, N.; Kumar, A.; Lozach, O.; Meijer, L. Bioorg. Med. Chem. 2006, 14, 3758.

  3. (a) Pandey, A.; Dewangan, D.; Verma, S.; Mishra, A.; Dubey, R. D. Int. J. ChemTech Res. 2011, 3, 178. (b) Chandramouli; Shivanand, M. R.; Nayanbhai, T. B.; Bheemachari; Udupi, R. H. J. Chem. Pharm. Res. 2012, 4, 1151. (c) Chinnasamy, R. P.; Sundararajan, R.; Govindaraj, S. J. Adv. Pharm. Technol. Res. 2010, 1, 342.

  4. (a) Venkatesh, P. Asian J. Pharm. Health Sci. 2011, 1, 8. (b) Vibhute, A. Y.; Junne, S. B.; Gurav, V. M.; Vibhute, Y. B. J. Chem. Pharm. Res. 2010, 2, 300.

  5. Chaubey, A. K.; Pandeya, S. N. Int. J. PharmTech Res. 2012, 4, 590.

    CAS  Google Scholar 

  6. Aboul-Fadl, T.; Mohammed, F. A.-H.; Hassan, E. A.-S. Arch. Pharmacal Res. 2003, 26, 778.

    Article  CAS  Google Scholar 

  7. (a) Tripathi, A. C.; Gupta, S. J.; Fatima, G. N.; Sonar, P. K.; Verma, A.; Saraf, S. K. Eur. J. Med. Chem. 2014, 72, 52. (b) Wadher, S. J.; Puranik, M. P.; Karande, N. A.; Yeole, P. G. Int. J. PharmTech Res. 2009, 1, 22. (c) Prasad, S. A. K.; Subrahmanyam, E. V. S.; Shabaraya, A. R. World J. Pharm. Res. 2014, 2, 2741.

  8. Mikhedkina, E. I.; Ananieva, V. V.; Tsygankov, A. V.; Osolodchenko, T. P.; Ponomarenko, S. V.; Chebanov, V. A. Funct. Mater. 2021, 28, 587.

    CAS  Google Scholar 

  9. Dimroth, O.; Zoeppritz, R. Ber. Dtsch. Chem. Ges. 1902, 35, 995.

    Google Scholar 

  10. Fischer, H.; Weiβ, B.; Schubert, M. Ber. Dtsch. Chem. Ges. 1923, 5, 1194.

    Article  Google Scholar 

  11. (a) Gholap, S. S. Eur. J. Med. Chem. 2016, 110, 13. (b) Kanaoka, Y.; Ilkeuchi, Y.; Kawamoto, T.; Bessho, K.; Akimoto, N.; Mikata, Y.; Nishida, M.; Yano, S.; Sasaki, T.; Yoneda, F. Bioorg. Med. Chem. 1998, 6, 301. (c) Bijev, A.; Radev, I.; Borisova, Y. Pharmazie 1999, 55, 568. (d) Sathe, B. S.; Jaychandran, E.; Jagtap, V. A.; Sreenivasa, G. M. Int. J. Pharm. Res. Dev. 2011, 3, 164. (e) Sashidhara, K. V.; Kumar, A.; Bahita, G.; Khan, M. M.; Khanna, A. K.; Saxena, J. K. Eur. J. Med. Chem. 2009, 44, 1813. (f) Kulkarni, A. A.; Wankhede, S. B.; Dhawale, N. D.; Yadav, B. B.; Deore, V. V.; Gonjari, I. D. Arabian J. Chem. 2017, 10, S184.

  12. Aydoğan, F.; Öcal, N.; Turgut, Z.; Yolaçan, Ç. Bull. Korean Chem. Soc. 2001, 22, 476.

    Google Scholar 

  13. Chate, A. V.; Tathe, A. G.; Nagtilak, P. J.; Sangle, S. M.; Gill, C. H. Chin. J. Catal. 2016, 37, 1997.

    Google Scholar 

  14. Swami, M. B.; Kaminwar, N. S.; More, Y. W.; Pathare, P. G.; Kótai, L.; Kendrekar, P.; Pawar, R. Eur. Chem. Bull. 2017, 6, 98.

    Article  CAS  Google Scholar 

  15. Sayyed, M.; Mokle, S.; Bokhare, M.; Mankar, A.; Surwase, S.; Bhusare, S.; Vibhute, Y. ARKIVOC 2006, (ii), 187.

  16. (a) Akishina, E. A.; Kazak, D. V.; Dikusar, E. A.; Zalesskaya, E. G.; Zhukovskaya, N. A.; Stepin, S. G.; Potkin, V. I. Russ. J. Gen. Chem. 2020, 90, 1432. (b) Dikusar, E. A.; Potkin, V. Y.; Kozlov, N. H. Benzaldegidy vanilinovogo ryada. Sintez proizvodnyh, primenenie i biologicheskaya aktivnost (Benzaldehydes of the Vanillin Series. Synthesis of derivatives, Aapplication, and Biological Activity [in Russian]); Lambert Academic Publishing, 2012.

  17. Saleem, L. M. N. Org. Magn. Reson. 1982, 19, 176.

  18. Aboul-Fadl, T.; Mohammed, F. A.; Hassan, E. A. Arch. Pharmacal Res. 2003, 26, 778.

  19. (a) Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3. (b) Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

  20. Kutsanian, A. A.; Popova, N. V.; Komisarenko, M. A. Ukr. Biopharm. J. 2020, 2, 76.

    Article  Google Scholar 

  21. Borodina, N.; Raal, A.; Kovalyov, V.; Osolodchenko, T.; Koshovyi, O.; Nguyen, H. T.; Komissarenko, A. Open Agric. J. 2020, 14, 136.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. National Technical University “Kharkiv Polytechnic Institute”, 2 Kyrpychova St., Kharkiv, 61002, Ukraine

    Olena I. Mikhedkina, Valeriia V. Ananieva, Igor I. Melnyk, Vladyslav O. Vereshchak & Alexander V. Tsygankov

  2. Mechnikov Institute of Microbiology and Immunology, National Academy of Medical Sciences of Ukraine, 14 Pushkinska St, Kharkiv, 61057, Ukraine

    Tetiana P. Osolodchenko

  3. Division of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals”, NationalAcademyofSciencesofUkraine, 60 Nauky Ave, Kharkiv, 61072, Ukraine

    Yana I. Sakhno, Svitlana V. Shishkina, Alexander V. Tsygankov & Valentyn A. Chebanov

  4. Faculty of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq, Kharkiv, 61022, Ukraine

    Svitlana V. Shishkina & Valentyn A. Chebanov

Authors
  1. Olena I. Mikhedkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Valeriia V. Ananieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yana I. Sakhno
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Igor I. Melnyk
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Vladyslav O. Vereshchak
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Tetiana P. Osolodchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Svitlana V. Shishkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Alexander V. Tsygankov
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Valentyn A. Chebanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Alexander V. Tsygankov or Valentyn A. Chebanov.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(6/7), 449–455

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 931 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mikhedkina, O.I., Ananieva, V.V., Sakhno, Y.I. et al. Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid. Chem Heterocycl Comp 59, 449–455 (2023). https://doi.org/10.1007/s10593-023-03215-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-023-03215-w

Keywords

Search

Navigation