Synthesis and characterization of thiazolidine-4-one and thiazine-4-one derived from 2-aminoterephthalic acid by microwave method

Abdullah Khalid Shehab; Malath Khalaf Rasheed

doi:10.53730/ijhs.v6nS2.7755

Authors

Abdullah Khalid Shehab
us4010520007@uosamarra.edu.iq
Department of Chemistry, College of Education, University of Samarra, Samarra, Iraq
Malath Khalaf Rasheed Department of Chemistry, College of Education, University of Samarra, Samarra, Iraq

Keywords:

Schiff base, thiazolidine-4-one, thiazine-4-one, antibacterial

Abstract

The Schiff bases (A1 - A5) were produced from the reaction of the 2-aminoterephthalic acid with a variety of aldehydes by microwave method. Thiazolidine-4- one compoundes (A6 - A10)were of the reaction of the prepared schiffbases with thioglycolic acid in equal molar proportions. Thiazine-4- one compounds (A11 - A15) were prepared from the prepared schiff bases with the amino acid (cysteine). The prepared compounds were diagnosed by Spectroscopic methods (IR, 1H-NMR). The biological activity against two types of bacteria Proteus mirabilis –GVe and Enterococcus faecalis +GVe have tested and compared with the ciprofloxacin drug. The results proved that the prepared compounds are effective against these bacteria.

Downloads

Download data is not yet available.

References

Xu R, Aotegen B, Zhong Z. Preparation and antibacterial activity of C2-benzaldehyde-C6-aniline double Schiff base derivatives of chitosan. International Journal of Polymeric Materials and Polymeric Biomaterials. 2018 Feb 11;67(3):181-91.

Patil PR, Vakhariya RR, Magdum CS. Solubility as well as Bioavailability Enhancement Techniques. Research Journal of Pharmaceutical Dosage Forms and Technology. 2019;11(2):105-10.

Sunil K, Kumara TP, Kumar BA, Patel SB. Synthesis, Characterization and Antiioxidant Activity of Schiff Base Compounds Obtained Using Green Chemistry Techniques. Pharmaceutical Chemistry Journal. 2021 Apr;55(1):46-53.

Hanna. H, Juncheng .Z, Zude .O, Zhou.B, Meiying.L and Liu.Y, ",Journal of Natueal Science", Wuhan University, 2010,1, 15, 7177,.

Fekri LZ, Hamidian H, Chekosarani MA. Urazolium diacetate as a new, efficient and reusable Brønsted acid ionic liquid for the synthesis of novel derivatives of thiazolidine-4-ones. RSC Advances. 2020;10(1):556-64.

Sankar PS, Divya K, Padmaja A, Padmavathi V. Synthesis and antimicrobial activity of azetidinone and thiazolidinone derivatives from azolylindolyl Schiff’s bases. Med Chem. 2017;7:340-7.

Djukic M, Fesatidou M, Xenikakis I, Geronikaki A, Angelova VT, Savic V, Pasic M, Krilovic B, Djukic D, Gobeljic B, Pavlica M. In vitro antioxidant activity of thiazolidinone derivatives of 1, 3-thiazole and 1, 3, 4-thiadiazole. Chemico-Biological Interactions. 2018 Apr 25;286:119-31.

Nahi RJ. Combination of 1, 2, 3-Triazole, Furan and Thiazolidin-4-one Structures For Potential Pharmaceutical Applications. International Journal of Pharmaceutical Research. 2020 Jun (1).

Britannica, The Editors of Encyclopaedia. "thiazine". Encyclopedia Britannica, 27 Nov, 2018.

Mohammed LA, Nief OA, Askar FW, Majeed AH. Synthesis, Characterization and Antimicrobial Activities of Silver Nanoparticles coated [1, 3] Thiazin-4-One derivatives. InJournal of Physics: Conference Series 2019 Sep 1 (Vol. 1294, No. 5, p. 052028). IOP Publishing.

Wang SQ, Yan XW, Hu BL, Zhang XG. Transition-metal and base-free thioannulation of propynamides with sodium sulfide and dichloromethane for the selective synthesis of 1, 3-thiazin-4-ones and thiazolidine-4-ones. Tetrahedron. 2020 Mar 20;76(12):131021.

Adnan S, Ghafil A. Synthesis and Identification of New (azo-heterocyclic) Derivatives and Study of their Biological Activity as Anti-bacteria and Fungi, , 2020 November; DOI: 10.25258/ijddt.11.1.10.

Szilágyi T. Infrared Spectroscopy of Adsorbed Hydrogen. InHydrogen Effects in Catalysis 2020 Sep 10 (pp. 183-193). CRC Press.

Korobatova NM, Shtenberg MV, Ivanova TN, Koroleva ON. Raman and IR Spectroscopy of Na 2 O–SiO 2–GeO 2 System. InMinerals: Structure, Properties, Methods of Investigation 2020 (pp. 95-100). Springer, Cham.

Salvino RA, Celebre G, De Luca G. Molecular Characterization of the Organic Fraction of Municipal Solid Waste and Compositional Evolution during Oxidative Processes Assessed by HR-MAS 13C NMR Spectroscopy. Applied Sciences. 2021 Jan;11(5):2267.

Kainosho M, Miyanoiri Y, Takeda M. Isotope-aided methods for biological NMR spectroscopy: past, present, and future. InExperimental Approaches of NMR Spectroscopy 2018 (pp. 37-61). Springer, Singapore.

Saito T, Yamano M, Nakayama K, Kawahara S. Quantitative analysis of crosslinking junctions of vulcanized natural rubber through rubber-state NMR spectroscopy. Polymer Testing. 2021 Apr 1;96:107130.

Zijenah LS. The world health organization recommended TB diagnostic tools. Tuberculosis. 2018 Sep 26;2:71-90.

Bhole RP, Chikhale RV, Wavhale RD, Asmary FA, Almutairi TM, Alhajri HM, Bonde CG. Design, synthesis and evaluation of novel enzalutamide analogues as potential anticancer agents. Heliyon. 2021 Mar 1;7(3):e06227.

Haines J, Tempowski J. Contribution of the World Health Organization to toxicology and poisons centers. InHistory of Modern Clinical Toxicology 2022 Jan 1 (pp. 493-504). Academic Press.