Synthesis, Characterization and Biological Evaluation of Some New Heterocyclic Compounds Derived from 2-Naphthol

Trifa  Khalaf  Mohammed; Media Noori Abdullah; Rostam Rasul Braiem

doi:10.21271/ZJPAS.32.3.12

Authors

Trifa Khalaf Mohammed Chamchamal Technical institute/ Sulaimani Polytechnic University, Iraq
Media Noori Abdullah Department of Chemistry, College of Science, Salahaddin University-Erbil, Kurdistan Region, Iraq
Rostam Rasul Braiem Department of Chemistry, College of Science, Salahaddin University-Erbil, Kurdistan Region, Iraq

DOI:

https://doi.org/10.21271/ZJPAS.32.3.12

Keywords:

Three component reaction, Heterocyclic compound, Thiazole, Thiazolidin-4-one, 1,2-dihydro-3H-1,2,4-triazol-3-one, antibacterial and antifungal activities.

Abstract

The present study deals with the synthesis, spectroscopic characterization, antibacterial and antifungal activities of novel series five-membered ring heterocyclic compounds containing nitrogen and sulfur heteroatoms. The synthetic routes have been divided into two parts: The first one includes synthesis of compounds (4a-c) through one pot operation three component reaction of 2-naphthol (1), substituted benzaldehyde (2a-c) and thiourea (3) in 1,2-dichloromethane, using a catalytic amount of ZrOCl₂.8H₂O and compound (6) was synthesized using semicarbazide (5) in absolute ethanol and indium (III) chloride as catalyst. The second part is the hetero-cyclization reactions of the compounds (4a-c and 6) to obtain the heterocyclic compounds (7a-c, 8, and 9). The structures of the synthesized products are verified on the basis of (FT-IR, ¹H-NMR and ¹³C-NMR) spectroscopy. The synthesized compounds antibacterial activities were screened against Staphylococcus aureus (Gram positive) and Escherichia coli (Gram negative) bacteria as compared to standard amikacin and antifungal activity against Candida albicans fungi as compared to standard Nystatin, well diffusion method is used. The antibacterial and antifungal activities of synthesized compounds (7a-c, 8 and 9) were higher than the antibacterial and antifungal activities of synthesized compounds (4a-c and 6).

References

ABDULLAH, M. N. 2014. Environmentally Benign Approach to the Synthesis of Some New Thiazolidinone Derivatives. Zanco Journal of Pure and Applied Sciences 26, 1-12.

AL-MULLA, A. 2017. A review: biological importance of heterocyclic compounds. Der Pharma Chemica, 9(13), 141-1472.

ALI, R. A., AMER, Z. & AL-TAMIMI, E. O. 2018. Synthesis and characterization of substituted 1, 2, 4-triazole and their derivatives on poly ethylene. Journal of Pharmaceutical Sciences and Research, 10, 1079-1084.

AYATI, A., EMAMI, S., ASADIPOUR, A., SHAFIEE, A. & FOROUMADI, A. 2015. Recent applications of 1, 3-thiazole core structure in the identification of new lead compounds and drug discovery. European journal of medicinal chemistry, 97, 699-718.

BHOSALE, P., CHAVAN, R. & BHOSALE, A. 2012. Design, synthesis, biological evaluation of thiazolyl Schiff base derivatives as novel anti-inflammatory agents. Indian Journal of Chemistry, 51B, 1649-1654.

CHUNDURU, V. S. & RAO, V. R. 2010. Synthesis of coumarin-substituted thiazolyl-pyrazolone derivatives via one-pot reaction. Journal of Sulfur Chemistry, 31, 545-550.

DE AQUINO, T. M., LIESEN, A. P., DA SILVA, R. E., LIMA, V. T., CARVALHO, C. S., DE FARIA, A. N. R., DE ARAUJO, J. M., DE LIMA, J. G., ALVES, A. J. & DE MELO, E. J. 2008. Synthesis, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene) hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids. Bioorganic & medicinal chemistry, 16, 446-456.

GURUMURTHI, S., SUNDARI, V. & VALLIAPPAN, R. 2009. Synthesis and biological evalution of some thiazolidinone derivatives of acyclic and cyclic ketones as antibacterial agents. Oriental Journal of Chemistry, 25(3), 615-619.

KAPOOR, G., PATHAK, D. P., BHUTANI, R. & KANT, R. 2016. Thiazolidinone as a pharmacologically active molecule. J Chem Pharm Res, 8(4), 151-68.

KAUR, P. & CHAWLA, A. 2017. 1, 2, 4-Triazole: a review of pharmacological activities. International Research Journal of Pharmacy, 8(7), 10-29.

KUBBA, A. A. M. & RAHIM, N. A. 2018. Synthesis, Characterization and Antimicrobial Evaluation with DFT Study of New Two-Amino-4-(4-Chlorophenyl) Thiazole Derivatives. Iraqi Journal of Pharmaceutical Sciences (P-ISSN: 1683-3597, E-ISSN: 2521-3512), 27, 79-88.

KUMAR, R. & PATIL, S. 2017. Biological prospective of 4-thiazolidinone: a review. Hygeia Journal for drugs and medicines, 9, 80-97.

LANDAGE, V., THUBE, D. & KARALE, B. 2019. Synthesis, characterisation and antimicrobial screening of some new thiazolyl chromones and pyrazoles. Indian journal of chemistry, 58B, 916-920.

NAGAWADE, R. R. & SHINDE, D. B. 2007. Zirconyl (IV) Chloride--Catalyzed Multicomponent Reaction of β-Naphthols: An Expeditious Synthesis of Amidoalkyl Naphthols. Acta Chimica Slovenica, 54, 642-646.

NIRWAN, S., CHAHAL, V. & KAKKAR, R. 2019. Thiazolidinones: Synthesis, Reactivity, and Their Biological Applications. Journal of Heterocyclic Chemistry, 56, 1239-1253.

PEJCHAL, V., PEJCHALOVÁ, M. & RŮŽIČKOVÁ, Z. 2015. Synthesis, structural characterization, antimicrobial and antifungal activity of substituted 6-fluorobenzo [d] thiazole amides. Medicinal Chemistry Research, 24, 3660-3670.

POURAMIRI, B. & KERMANI, E. T. 2017. Lanthanum (III) chloride/chloroacetic acid as an efficient and reusable catalytic system for the synthesis of new 1-((2-hydroxynaphthalen-1-yl)(phenyl) methyl) semicarbazides/thiosemicarbazides. Arabian Journal of Chemistry, 10, S730-S734.

ROUF, A. & TANYELI, C. 2015. Bioactive thiazole and benzothiazole derivatives. European journal of medicinal chemistry, 97, 911-927.

SHALINI, M., YOGEESWARI, P., SRIRAM, D. & STABLES, J. 2009. Cyclization of the semicarbazone template of aryl semicarbazones: synthesis and anticonvulsant activity of 4, 5-diphenyl-2H-1, 2, 4-triazol-3 (4H)-one. Biomedicine & pharmacotherapy, 63, 187-193.

SHNEINE, J. K. & ALARAJI, Y. H. 2016. Chemistry of 1, 2, 4-triazole: A review article. International Journal of Science and Research (IJSR), 5, 1411-1423.

SUSHILKUMAR, S. B. & DEVANAND, B. S. 2003. Synthesis and Anti-inflammatory Activity of [2-(Benzothiazol-2-ylimino)-4-oxo-3-phenylthiazolidin-5-yl]-acetic acid derivatives. Journal of the Korean Chemical Society, 47, 237-240.

TAYLOR, A. P., ROBINSON, R. P., FOBIAN, Y. M., BLAKEMORE, D. C., JONES, L. H. & FADEYI, O. 2016. Modern advances in heterocyclic chemistry in drug discovery. Organic & biomolecular chemistry, 14, 6611-6637.

TOCHE, R. & DESHMUKH, S. U. 2017. A Review on some Thiazole Containing Heterocyclic Compounds and their Biological Activity. International Journal of Science and Research in Science and Technology, 3, 20-25

YOUNIS, M. N., ZIWAR G. B., ABDULLA, M. N. 2012.. Green Approach: Multi component Reaction of alpha and beta-Naphthols Using Zirconyl(IV) Chlorid Catalyst. Zanco Journal of Pure and Applied Science, 24, 67-76.