One pot and stepwise synthesis of some new azo thiazolidin-4-one derivatives and their biological evaluations.

Authors

  • Chinar M. Burhan 1Department of Chemistry, College of Education, Salahaddin University–Erbil, Erbil-Kurdistan, Iraq
  • Awaz J. Hussein Department of Chemistry, College of Education, Salahaddin University–Erbil, Erbil-Kurdistan, Iraq

DOI:

https://doi.org/10.21271/ZJPAS.35.1.16

Keywords:

Heterocyclic compound, Schiff base, thiazolidinone, mercapto acetic acid, biological activity.

Abstract

(2-(2-(benzyloxy)-5-((4-(6-methylbenzo[d]thiazol-2-yl)phenyl)diazenyl)phenyl)-3- substitutedphenylthiazolidin-4-ones  derivatives (4a-h) have been synthesized from the reaction of 2-(benzyloxy)-5-((4-(6-methylbenzo[d]thiazol-2-yl) phenyl)diazenyl)benzaldehyde (2)  with different substituted aniline, followed by cyclization with mercaptoacetic acid via either a one-pot three-component condensation and stepwise process. The structure of synthesized compounds were elucidated by FT-IR, 1H-NMR, 13C-NMR and DEPT 13C NMR. Finally, the animicrobile activity of these compounds were evaluated by the well diffusion assay against S. aureus Gram-positive and E. coli Gram-negative bacteria.

References

ALMASIRAD, A., GHADIMI, M., MIRAHMADI, S., AHMADIAN KODAKAN, P., JAHANI, R., NAZARI, M., REZAEE, E.,AZIZIAN, H., RABIZADEH, P., TABATABAI, S.A. AND FAIZI, M., 2022. Design, synthesis, and preliminary pharmacological evaluation of novel thiazolidinone derivatives as potential benzodiazepine agonists. Molecular Diversity, 26(2), pp.769-780.

AYOOB, M.M., HAWAIZ, F.E., HUSSEIN, A., SAMAD, M.K., HUSSAIN, F. AND MOHAMED, S.K., 2020. Synthesis, Spectroscopic Investigation, Anti-Bacterial and Antioxidant Activites of Some New Azo-Benzofuran Derivatives. Egyptian Journal of Chemistry, 63(7), pp.2617-2629.

AYOOB, MZGIN MOHAMMED; HAWAIZ, FAROUQ EMAM (2017). AIP Conference Proceedings [Author(S) 6th International Conference And Workshops On Basic And Applied Sciences - Erbil, Kurdistan, Iraq (18–19 March 2017)] - Design, Synthesis, And Spectroscopic Study Of Some New Flavones Containing Two Azo Linkages. , 1888(), 020017–.

BROWN, F.C., 1961. 4-Thiazolidinones. Chemical Reviews, 61(5), pp.463-521.

DESAI, N.C., JADEJA, K.A., JADEJA, D.J., KHEDKAR, V.M. AND JHA, P.C., 2021. Design, synthesis, antimicrobial evaluation, and molecular docking study of some 4-thiazolidinone derivatives containing pyridine and quinazoline moiety. Synthetic Communications, 51(6), pp.952-963.

BEKTAŞ, H., CEYLAN, Ş., DEMIRBAŞ, N., ALPAY-KARAOĞLU, Ş. AND SÖKMEN, B.B., 2013. Antimicrobial and antiurease activities of newly synthesized morpholine derivatives containing an azole nucleus. Medicinal Chemistry Research, 22(8), pp.3629-3639.

HOLOTA, S., KRYSHCHYSHYN, A., DERKACH, H., TRUFIN, Y., DEMCHUK, I., GZELLA, A., GRELLIER, P. AND LESYK, R., 2019. Synthesis of 5-enamine-4-thiazolidinone derivatives with trypanocidal and anticancer activity. Bioorganic chemistry, 86, pp.126-136.

HUSSEIN, A.J., 2014. Synthesis and characterization of some new pyrazoline compounds derived from azo-benzaldehyde. ZANCO Journal of Pure and Applied Sciences, 27(1), pp.51-58.

HUSSEIN, AWAZ JAMIL; JALAL AZEEZ, HASHIM (2013). Synthesis and Antimicrobial Activity of Some New Thiazolidin-4-one Derivatives of 4-(6-methylbenzo[d]thiazol-2-yl)benzamine. Journal of Chemistry, 2013(), 1–6.

JAIN, A.K., VAIDYA, A., RAVICHANDRAN, V., KASHAW, S.K. AND AGRAWAL, R.K., 2012. Recent developments and biological activities of thiazolidinone derivatives: A review. Bioorganic & medicinal chemistry, 20(11), pp.3378-3395.

KERIM BABAOGLU; MARK A. PAGE; VICTORIA C. JONES; MICHAEL R. MCNEIL; CHANGJIANG DONG; JAMES H. NAISMITH; RICHARD E. LEE (2003). Novel inhibitors of an emerging target in Mycobacterium tuberculosis; substituted thiazolidinones as inhibitors of dTDP-rhamnose synthesis. , 13(19), 3227–3230.

MALIPEDDI, H., KARIGAR, A.A., MALIPEDDI, V.R. AND SIKARWAR, M.S., 2012. Synthesis and antitubercular activity of some novel thiazolidinone derivatives. Tropical Journal of Pharmaceutical Research, 11(4), pp.611-620.

MASHRAI, A., DAR, A. AND MIR, S., 2016. SHAMSUZZAMAN (2016). Strategies for the Synthesis of Thiazolidinone Heterocycles. Med. Chem. (Los Angeles), 6, pp.280-291.

NIRWAN, S., CHAHAL, V. AND KAKKAR, R., 2019. Thiazolidinones: Synthesis, reactivity, and their biological applications. Journal of Heterocyclic Chemistry, 56(4), pp.1239-1253.

OUBELLA, A., EL MANSOURI, A.E., FAWZI, M., BIMOUSSA, A., LAAMARI, Y., AUHMANI, A., MORJANI, H., ROBERT, A., RIAHI, A. AND ITTO, M.Y.A., 2021. Thiazolidinone-linked1, 2, 3-triazoles with monoterpenic skeleton as new potential anticancer agents: Design, synthesis and molecular docking studies. Bioorganic Chemistry, 115, p.105184.

PATEL, D., KUMARI, P. AND PATEL, N., 2012. Synthesis and biological evaluation of some thiazolidinones as antimicrobial agents. European journal of medicinal chemistry, 48, pp.354-362.

SINGH, SHIVA P.; PARMAR, SURENDRA S.; RAMAN, KRISHNA; STENBERG, VIRGIL I. (1981). Chemistry and biological activity of thiazolidinones., 81(2), 175–203.

TAHMASVAND, R., BAYAT, P., VAHDANIPARAST, S.M., DEHGHANI, S., KOOSHAFAR, Z., KHALEGHI, S., ALMASIRAD, A. AND SALIMI, M., 2020. Design and synthesis of novel 4-thiazolidinone derivatives with promising anti-breast cancer activity: Synthesis, characterization, in vitro and in vivo results. Bioorganic Chemistry, 104, p.104276.

VEERASAMY, R., RAJAK, H., SURESH KUMAR, K. AND KISHORE AGRAWAL, R., 2011. Synthesis and evaluation of antimicrobial activity of thiazolidinone derivatives. Letters in Drug Design & Discovery, 8(1), pp.82-86

Published

2023-02-20

How to Cite

Chinar M. Burhan, & Awaz J. Hussein. (2023). One pot and stepwise synthesis of some new azo thiazolidin-4-one derivatives and their biological evaluations. Zanco Journal of Pure and Applied Sciences, 35(1), 151–164. https://doi.org/10.21271/ZJPAS.35.1.16

Issue

Section

Biology, Chemistry and Medical Researches