In a one-pot reaction involving 3-(2-aminothiazol-5-yl)-2H-chromen-2-one/5-(naphthalen-1-yl)thiazol-2-amines 5-6 with various substituted aldehydes and mercaptoacetic acid, we obtained the corresponding 2-(4-substituted-phenyl)-3-[5-(2-oxo-2H-chromen-3-yl)thiazol-2-yl] thiazolidin-4-ones 8(a-h) and 2-(4-substituted-phenyl)-3-[5-(naphthalen-1-yl)thiazol-2-yl] thiazolidin-4-ones 9(a-h). The antimicrobial activity of all compounds was evaluated against Pseudomonas aeruginosa (MTCC-424), Salmonella typhi (MTCC-531), Staphylococcus aureus (MTCC-737), and Candida albican (MTCC-227). Molecular docking further supported the findings, which showed that the compounds 8d and 9d had excellent antibacterial action against all tested pathogens.
Get full access to this article
View all access options for this article.
References
1.
BikoboDSN, VodnarDC, StanaA, et al.Synthesis of 2-phenylamino-thiazole derivatives as antimicrobial agents. J Saudi Chem Soc, 2017; 21(7):861–868; doi: 10.1016/j.jscs.2017.04.007
2.
MamidalaS, PeddiSR, AravilliRK, et al.Microwave irradiated one pot, three component synthesis of a new series of hybrid coumarin based thiazoles: Antibacterial evaluation and molecular docking studies. J Mol Struct, 2021; 1225:129114; doi: 10.1016/j.molstruc.2020.129114
3.
TheuretzbacherU, GottwaltS, BeyerP, et al.Analysis of the clinical antibacterial and antituberculosis pipeline. Lancet Infect Dis, 2019; 19(2):e40–e50; doi: 10.1016/S1473-3099(18)30513-9
4.
VachanB, KaruppasamyM, VinothP, et al.Proline and its derivatives as organocatalysts for multi‐component reactions in aqueous media: Synergic pathways to the green synthesis of heterocycles. Adv Synth Catal, 2020; 362(1):87–110; doi: 10.1002/adsc.201900558
5.
NirwanS, ChahalV, KakkarR. Thiazolidinones: Synthesis, reactivity, and their biological applications. Journal of Heterocyclic Chem, 2019; 56(4):1239–1253; doi: 10.1002/jhet.3514
6.
PawarS, KumarK, GuptaMK, et al.Synthetic and medicinal perspective of fused-thiazoles as anticancer agents. Anticancer Agents Med Chem, 2021; 21(11):1379–1402; doi: 10.2174/1871520620666200728133017
7.
AgrawalN. Synthetic and therapeutic potential of 4-thiazolidinone and its analogs. Curr Chem Lett, 2021; 10(2):119–138; doi: 10.5267/j.ccl.2020.11.002
8.
PuliciM, QuartieriF. Traceless solid-phase synthesis of 2-amino-5-alkylidene-thiazol-4-ones. Tetrahedron Lett, 2005; 46(14):2387–2391; doi: 10.1016/j.tetlet.2005.02.059
9.
RoszczenkoP, HolotaS, SzewczykOK, et al.4-Thiazolidinone-bearing hybrid molecules in anticancer drug design. Int J Mol Sci, 2022; 23(21):13135; doi: 10.3390/ijms232113135
10.
HarounM, FesatidouM, PetrouA, et al.Identification of novel cyclooxygenase-1 selective inhibitors of thiadiazole-based scaffold as potent anti-inflammatory agents with safety gastric and cytotoxic profile. Molecules, 2023; 28(8):3416; doi: 10.3390/molecules28083416
11.
NanjanM, MohammedM, KumarBP, et al.Thiazolidinediones as antidiabetic agents: A critical review. Bioorg Chem, 2018; 77:548–567; doi: 10.1016/j.bioorg.2018.02.009
12.
TajM, RaheelA, AlelwaniW, et al.Mechanochemical synthesis of thiazolidinone-triazoles derivatives as antidiabetic agents: Pharmacokinetics, molecular docking, and in vitro antidiabetic properties. Russ J Gen Chem, 2023; 93(4):912–919; doi: 10.1134/S1070363223040199
13.
das NevesAM, BerwaldtGA, AvilaCT, et al.Synthesis of thiazolidin-4-ones and thiazinan-4-ones from 1-(2-aminoethyl) pyrrolidine as acetylcholinesterase inhibitors. J Enzyme Inhib Med Chem, 2020; 35(1):31–41; doi: 10.1080/14756366.2019.1680659
14.
VaghasiyaMD, MendaparaJV, VaghasiyaSP, et al.Identification of novel 4-thiazolidinones as new TcaR inhibitors: Design, synthesis, molecular docking, MD simulation, ADMET and in vitro antibacterial evaluation. J Mol Struct, 2023; 1294:136308; doi: 10.1016/j.molstruc.2023.136308
15.
CheeralaVSK, AkhirA, SaxenaD, et al.Discovery of benzoxazole–thiazolidinone hybrids as promising antibacterial agents against Staphylococcus aureus and Enterococcus species. RSC Med Chem, 2023; 14(9):1712–1721; doi: 10.1039/D3MD00290J
16.
EissaSI, FarragAM, AbbasSY, et al.Novel structural hybrids of quinoline and thiazole moieties: Synthesis and evaluation of antibacterial and antifungal activities with molecular modeling studies. Bioorg Chem, 2021; 110:104803; doi: 10.1016/j.bioorg.2021.104803
17.
PetrouA, GeronikakiA, KartsevV, et al.N-Derivatives of (Z)-Methyl 3-(4-Oxo-2-thioxothiazolidin-5-ylidene) methyl)-1H-indole-2-carboxylates as antimicrobial agents—In silico and in vitro evaluation. Pharmaceuticals, 2023; 16(1):131; doi: 10.3390/ph16010131
18.
BakrRB, ElkanziNA. Preparation of some novel thiazolidinones, imidazolinones, and azetidinone bearing pyridine and pyrimidine moieties with antimicrobial activity. Journal of Heterocyclic Chem, 2020; 57(7):2977–2989; doi: 10.1002/jhet.4009
19.
EryılmazS, ÇelikoğluET, İdilÖ, et al.Derivatives of pyridine and thiazole hybrid: Synthesis, DFT, biological evaluation via antimicrobial and DNA cleavage activity. Bioorg Chem, 2020; 95:103476; doi: 10.1016/j.bioorg.2019.103476
20.
JayashreeB, AnuradhaD, VenugopalaK. Synthesis and characterization of Schiff bases of 2′-amino-4′-(6-chloro-3-coumarinyl)-thiazole as potential NSAIDs. Asian J Chem, 2005; 17(4):2093.
21.
AnsariMI, KhanSA. Synthesis and antimicrobial activity of some novel quinoline-pyrazoline-based coumarinyl thiazole derivatives. Med Chem Res, 2017; 26(7):1481–1496; doi: 10.1007/s00044-017-1855-4
22.
BrindhaJ, Fen RejiTFA. Synthesis and molecular docking studies of coumarinyl thiazole as cell division protein kinase 2 inhibitor. Asian J Chem, 2019; 31(11):2453–2456; doi: 10.1423/3/ajchem.2019.22106
23.
Abedi-JaziniZ, SafariJ, ZarnegarZ, et al.A simple and efficient method for the synthesis of 2-aminothiazoles under mild conditions. Polycycl Aromat Compd, 2018; 38(3):231–235; doi: 10.1080/10406638.2016.1200104
24.
RawalRK, TripathiR, KattiS, et al.Synthesis and evaluation of 2-(2, 6-dihalophenyl)-3-pyrimidinyl-1, 3-thiazolidin-4-one analogues as anti-HIV-1 agents. Bioorg Med Chem, 2007; 15(9):3134–3142; doi: 10.1016/j.bmc.2007.02.044
25.
BhatMA, Al-OmarMA, SiddiquiN. Synthesis of 2-(substituted phenyl)-3-[5-(2-oxo-2H-chromen-3-yl)-1, 3, 4-oxadiazol-2-yl]-1, 3-thiazolidin-4-ones with antimicrobial activity. Acta Pol Pharm, 2011; 68(2):295–299.
26.
KhanMS, AgrawalR, UbaidullahM, et al.Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach. Heliyon, 2019; 5(10):e02615; doi: 10.1016/j.heliyon.2019.e02615
27.
Zabiulla KouserS, JoythiM, BegumAB, et al.Molecular docking, synthesis and antimicrobial evaluation of metal complexes with Schiff base. Results Chem, 2023; 5:100650; doi: 10.1016/j.rechem.2022.100650
28.
JaysJ, MohanS, SaravananJ. Molecular docking studies of novel aminopyrimidines as potent antifungal agents. Chem Methodol, 2019:3(4); doi: 10.2203/4/chemm.2018.151655.1100
29.
BittrichS, RoseY, SeguraJ, et al.RCSB Protein Data Bank: Improved annotation, search and visualization of membrane protein structures archived in the PDB. Bioinformatics, 2022; 38(5):1452–1454; doi: 10.1093/bioinformatics/btab813
30.
O’BoyleNM, BanckM, JamesCA, et al.Open Babel: An open chemical toolbox. J Cheminform, 2011; 3(1):33–14; doi: 10.1186/1758-2946-3-33
31.
EberhardtJ, Santos-MartinsD, TillackAF, et al.AutoDock Vina 1.2. 0: New docking methods, expanded force field, and python bindings. J Chem Inf Model, 2021; 61(8):3891–3898; doi: 10.1021/acs.jcim.1c00203
32.
StudioD. Discovery studio. Accelrys. 2008. Available from: www.3ds.com
