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Research Articles

One-pot reactions in the synthesis of thiazolidinone derivatives by nano-Fe3O4–cysteine catalyst

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Pages 655-670 | Received 07 Mar 2022, Accepted 30 May 2022, Published online: 24 Jun 2022

References

  • Campaigne E. Adrien Albert and the rationalization of heterocyclic chemistry. J Chem Educ. 1986;63:860.
  • Jain AK, Vaidya A, Ravichandran V, et al. Recent developments and biological activities of thiazolidinone derivatives: a review. Bioorg Med Chem. 2012;20:3378–3395.
  • Cascioferro S, Parrino B, Carbone D, et al. Thiazoles, their benzofused systems, and thiazolidinone derivatives: versatile and promising tools to combat antibiotic resistance. J Med Chem. 2020;63:7923–7956.
  • Irfan A, Batool F, Zahra Naqvi SA, et al. Benzothiazole derivatives as anticancer agents.J Enzyme Inhib Med Chem. 2020;35:265–279.
  • Pathak N, Rathi E, Kumar N, et al. A review on anticancer potentials of benzothiazole derivatives. Mini Rev Med Chem. 2020;20:12–23.
  • Asiri YI, Alsayari A, Muhsinah AB, et al. Benzothiazoles as potential antiviral agents. J Pharm Pharmacol. 2020;72:1459–1480.
  • Gjorgjieva M, Tomašič T, Kikelj D, et al. Benzothiazole-based compounds in antibacterial drug discovery. Curr Med Chem. 2018;25:5218–5236.
  • Panico AM, Vicini P, Geronikaki A, et al. Heteroarylimino-4-thiazolidinones as inhibitors of cartilage degradation. Bioorganic Chem. 2011;39:48–52.
  • Ammazzalorso A, Carradori S, Amoroso R, et al. 2-Substituted benzothiazoles as antiproliferative agents: novel insights on structure-activity relationships. Eur J Med Chem. 2020;207:112762.
  • Kaboudin B, Abbasi Shiran J. Novel one-pot four-component condensation cyclization reactions for the synthesis of thiazolidine-4-one and 3 H-thiazoles. J Sulfur Chem. 2018;39:633–645.
  • Mahmoodi NO, Mohammadgholipour S, Ghanbari Pirbasti F. Microwave-assisted one-pot three-component synthesis of thiazolidinones using KSF@ Ni as an efficient heterogeneous catalyst. J Sulfur Chem. 2017;38:668–678.
  • Ali SH, Sayed AR. Review of the synthesis and biological activity of thiazoles. Synth Commun. 2020;51:670–700.
  • Sayed A. Synthesis of bis-thiazoles, bis-pyrazoles, bis-hydrazonates, and bis-triazolothiadiazoles based on bis-hydrazonoyl and bis-hydrazones. Turk J Chem. 2015;39:600–609.
  • Farghaly TA, Abdallah MA, Khedr MA, et al. Synthesis, antimicrobial activity and molecular docking study of thiazole derivatives. J Heterocycl Chem. 2017;54:2417–2425.
  • Sayed AR. Synthesis of novel thiadiazoles and bis-thiadiazoles from carbonothioic dihydrazide. Tetrahedron Lett. 2010;51:4490–4493.
  • Gomha SM, Farghaly TA, Sayed AR. Design, synthesis, and characterization of some new bis-thiazoles. J Heterocycl Chem. 2017;54:1537–1542.
  • El-Hag FA, Gomha SM, Farghaly TA. Hydrazonoyl halides precursors to synthesis of new thiazole, thiadiazole, and benzothiazepine derivatives. J Heterocycl Chem. 2017;54:1172–1177.
  • Sayed AR, Gomha SM, Farghaly TA. Synthesis and characterization of bisimidazoles, bistriazoles, bisthiadiazoles, and bisthiazoles from novel bishydrazonoyl dichlorides. J Heterocycl Chem. 2016;53:255–262.
  • Kim KS, Rhee JS. Effect of acetylation on emulsifying properties of glycinin. J Agric Food Chem. 1990;38:669–674.
  • Carbone A, Cascioferro S, Parrino B, et al. Thiazole analogues of the marine alkaloid nortopsentin as inhibitors of bacterial biofilm formation. Molecules. 2021;26(1):81.
  • Korkmaz A, Bursal E. Benzothiazole sulfonate derivatives bearing azomethine: synthesis, characterization, enzyme inhibition, and molecular docking study. J Mol Struct. 2022;1257:132641.
  • Elgemeie GH, Shams HZ, Elkholy YM, et al. Novel synthesis of pyrido [2, 1-b] benzothiazoles and 1, 3-benzothiazole derivatives. Phosphorus Sulfur Silicon Relat Elem. 2000;165:265–272.
  • Eleftheriou P, Geronikaki A, Hadjipavlou-Litina D, et al. Fragment-based design, docking, synthesis, biological evaluation and structure–activity relationships of 2-benzo/benzisothiazoli-mino-5-aryliden-4-thiazolidinones as cycloxygenase/lipoxygenase inhibitors. Eur J Med Chem. 2012;47:111–124.
  • Türkeş C, Arslan M, Demir Y, et al. Synthesis, biological evaluation and in silico studies of novel N-substituted phthalazine sulfonamide compounds as potent carbonic anhydrase and acetylcholinesterase inhibitors. Bioorganic Chem. 2019;89:103004.
  • Vicini P, Geronikaki A, Incerti M, et al. 2-Heteroarylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: synthesis and structure–activity relationship. Bioorg Med Chem. 2008;16:3714–3724.
  • Roudsari ST, Rad-Moghadam K, Hosseinjani-Pirdehi H. Dual complex of amylose with iodine and magnetite nano-crystallites: enhanced superparamagnetic and catalytic performance for synthesis of spiro-oxindoles. Appl Organomet Chem. 2019;33:4993.
  • Norouzi FH, Foroughifar N, Khajeh-Amiri A, et al. A novel superparamagnetic powerful guanidine-functionalized γ-Fe2O3 based sulfonic acid recyclable and efficient heterogeneous catalyst for microwave-assisted rapid synthesis of quinazolin-4 (3H)-one derivatives in Green media. RSC Adv. 2021;11:29948–29959.
  • Li J, Gao H. A renewable potentiometric immunosensor based on Fe3O4 nanoparticles immobilized anti-IgG. Electroanal Int J Devoted Fundam Pract Asp Electroanal. 2008;20:881–887.
  • Babaei A, Afrasiabi M, Moghanian H. A new sensor based on the glassy carbon electrode modified with poly aspartic acid-Fe3O4 nanoparticle/multi-walled carbon nanotubes composite for a selective simultaneous determination of piroxicam and clopidogrel in the presence of uric acid. Anal Bioanal Electrochem. 2017;9:741–761.
  • Mohammadi H, Shaterian HR. γ-Aminobutyric acid hydrochloride supported on superparamagnetic γ-Fe2O3@SiO2 as a novel heterogeneous nanocatalyst for the synthesis of 2-amino-5-alkylidene-thiazol-4-one derivatives. J Iran Chem Soc. 2019;16:479–492.
  • Gholami Dehbalaei M, Foroughifar N, Khajeh-Amiri A, et al. N-propylbenzoguanamine sulfonic acid-functionalized magnetic nanoparticles: a novel and magnetically retrievable catalyst for the synthesis of 1, 4-dihydropyridine derivatives. J Chin Chem Soc. 2018;65:1356–1369.
  • Dehbalaei MG, Foroughifar N, Pasdar H, et al. N-propyl benzoguanamine sulfonic acid supported on magnetic Fe3O4 nanoparticles: a novel and efficient magnetically heterogeneous catalyst for the synthesis of 1, 8-dioxo-decahydroacridine derivatives. New J Chem. 2018;42:327–335.
  • Dehbalaei MG, Foroughifar N, Pasdar H, et al. Choline chloride based thiourea catalyzed highly efficient, eco-friendly synthesis and anti-bacterial evaluation of some new 6-amino-4-aryl-2, 4-dihydro-3-phenyl pyrano [2, 3-c] pyrazole-5-carbonitrile derivatives. Res Chem Intermed. 2017;43:3035–3051.
  • Mobinikhaledi A, Amiri AK. One-pot synthesis of tri-and tetrasubstituted imidazoles using eutectic salts as ionic liquid catalyst. Res Chem Intermed. 2015;41:2063–2070.
  • Mobinikhaledi A, Amiri AK. Natural eutectic salts catalyzed one-pot synthesis of 5-arylidene-2-imino-4-thiazolidinones. Res Chem Intermed. 2013;39:1491–1498.
  • Azizi N, Mobinikhaledi A, Amiri AK, et al. Catalyst-free synthesis of dihydropyridine from barbituric acid in water. Res Chem Intermed. 2012;38:2271–2275.
  • Safaei-Ghomi J, Ebrahimi SM. Nano-Fe3O4–cysteine as a superior catalyst for the synthesis of indeno [1, 2-c] pyrazol-4 (1H)-ones. Polycycl Aromat Compd. 2020;40:1–11.
  • Bankar SR. Nano-Fe3O4@ L-cysteine as an efficient recyclable organocatalyst for the green synthesis of bis (indolyl) methanes under microwave irradiation. Curr Organocatalysis. 2018;5:42–50.
  • Lagunin AA, Geronikaki A, Eleftheriou P, et al. Rational use of heterogeneous data in quantitative structure–activity relationship (QSAR) modeling of cyclooxygenase/lipoxygenase inhibitors. J Chem Inf Model. 2019;59:713–730.
  • Weber PN, Warren JJ. The interaction between methionine and two aromatic amino acids is an abundant and multifunctional motif in proteins. Arch Biochem Biophys. 2019;672:108053.
  • Orabi EA, English AM. Sulfur-aromatic interactions: modeling cysteine and methionine binding to tyrosinate and histidinium ions to assess their influence on protein electron transfer. Isr J Chem. 2016;56:872–885.
  • Dhal PN, Achary TE, Nayak A. Studies in the synthesis of thizaolidinones part 2, 5-benzal derivatives of 2-(substituted benzothiazole-2'-yl-imino)-4-thiazolidinones and their brominated products. Chem Informationsdienst. 1975;6:120–125.

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