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Synthesis of Bioactive Thioxoimidazolidinones, Oxazolidinones, Thioxothiazolidinones, Thiazolidinediones

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N-Heterocycles

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Abstract

The unique biological features of five-membered heterocycles, which particularly possess exocyclic double-bonded atoms such as sulfur and oxygen, encourage researchers to develop divergent synthetic strategies. Nanocatalysis can provide more sustainable, efficient, and less polluting methods; as a result, during the last decade, such type of syntheses have been aimed as green and efficient approaches. This chapter discusses the recent efficient research in nanocatalytic processes for the synthesis of bioactive thioxoimidazolidinones, Oxazolidinones, thioxothiazolidinones, and Thiazolidinediones.

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References

  • Agarwal S, Agarwal DK, Gautam N et al (2014) Synthesis and in vitro antimicrobial evaluation of benzothiazole incorporated Thiazolidin-4-ones derivatives. J Korean Chem Soc 58:33–38

    Article  CAS  Google Scholar 

  • Akhavan M, Foroughifar N, Pasdar H (2017) Copper(II)-complex functionalized magnetite nanoparticles: a highly efficient heterogeneous nanocatalyst for the synthesis of 5-arylidenthiazolidine-2,4-diones and 5-arylidene-2-thioxothiazolidin-4-one. Transit Met Chem 42:543–552

    Article  CAS  Google Scholar 

  • Azgomi N, Mokhtary M (2015) Nano-Fe3O4@SiO2 supported ionic liquid as an efficient catalyst for the synthesis of 1,3-thiazolidin-4-ones under solvent-free conditions. J Mol Catal A Chem 398:58–64

    Article  CAS  Google Scholar 

  • Barreca ML, Balzarini J, Chimirri A et al (2002) Design, synthesis, structure−activity relationships, and molecular modeling studies of 2,3-Diaryl-1,3-thiazolidin-4-ones as potent anti-HIV agents. J Med Chem 45:5410–5413

    Article  CAS  PubMed  Google Scholar 

  • Barros CD, Amato AA, de Oliveira TB et al (2010) Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPARγ ligands. Bioorg Med Chem 18:3805–3811

    Article  CAS  PubMed  Google Scholar 

  • Cantello BCC, Cawthorne MA, Haigh D, Hindley RM, Smith SA et al (1994) The synthesis of BRL 49653—a novel and potent antihyperglycaemic agent. Bioorg Med Chem Lett 4:1181–1184

    Article  CAS  Google Scholar 

  • Chang DM, Kwon DY, Kim YS (2013) Heteroleptic dual acceptor organic dyes with Rhodanine-3-Acetic Acid and Cyanoacrylic Acid. Mol Cryst Liq Cryst 585:100–106

    Article  CAS  Google Scholar 

  • Chen L, Noory Fajer A, Yessimbekov Z (2019) Diaryl sulfides synthesis: copper catalysts in C-S bond formation. J Sulfur Chem 40:451–468

    Article  CAS  Google Scholar 

  • Cunico W, Gomes CRB, de Lourdes M et al (2007) One-pot synthesis of 2-isopropyl-3-benzyl-1,3-thiazolidin-4-ones and 2-phenyl-3-isobutyl-1,3-thiazolidin-4-ones from valine, arenealdehydes and mercaptoacetic acid. Tetrahedron Lett 48:6217–6220

    Article  CAS  Google Scholar 

  • Cunico W, Gomes CRB et al (2008) Chemistry and biological activities of 1,3-Thiazolidin-4-ones. Mini Rev Org Chem 5:336–344

    Article  CAS  Google Scholar 

  • Deep A, Kumar P, Narasimhan B, Ramasamy K et al (2015) Synthesis, antimicrobial, anticancer evaluation of 2-(aryl)-4- thiazolidinone derivatives and their QSAR Studies. Curr Top Med Chem 15:990–1002

    Article  CAS  PubMed  Google Scholar 

  • Deep A, Narasimhan B, Mani V, Ramasamy K, Mishra RK, Lim S (2016) 4-Thiazolidinone derivatives: synthesis, antimicrobial, anticancer evaluation and QSAR studies. RSC Adv 6:109485–109494

    Article  CAS  Google Scholar 

  • El-Gaby MSA, Ismail ZH, Abdel-Gawad SM et al (2009) Synthesis of thiazolidine and thiophenederivatives for evaluation as anticancer agents. Phosphorus Sulfur Silicon Relat Elem 184:2645–2654

    Article  CAS  Google Scholar 

  • Esam Z, Akhavan M, Bekhradnia A et al (2020) A novel magnetic immobilized Para-Aminobenzoic Acid-Cu(II) complex: a green, efficient and reusable catalyst for aldol condensation reactions in green media. Catal Lett 150:3112–3131

    Article  CAS  Google Scholar 

  • Geronikaki AA, Lagunin AA et al (2008) Computer-aided discovery of anti-inflammatory thiazolidinones with dual Cyclooxygenase/Lipoxygenase inhibition. J Med Chem 51:1601–1609

    Article  CAS  PubMed  Google Scholar 

  • Ghosh S, Riyajuddin S, Sarkar S et al (2020) Pd NPs decorated on POPs as recyclable catalysts for the synthesis of 2-oxazolidinones from propargylic amines via atmospheric cyclizative CO2 incorporation. Chem Nano Mat 6:160–172

    Article  CAS  Google Scholar 

  • Gorodylova N, Kosinova V, Dohnalova Z et al (2013) New purple-blue ceramic pigments based onCoZr4(PO4)6. Dyes Pigm 98:393–404

    Article  CAS  Google Scholar 

  • Havrylyuk D, Zimenkovsky B, Vasylenko O et al (2013) Synthesis and anticancer and antiviral activities of new 2-Pyrazoline-substituted 4-Thiazolidinones. J Heterocycl Chem 50:E55–E62

    Article  CAS  Google Scholar 

  • Heravi MM, Zadsirjan V (2013) Oxazolidinones as chiral auxiliaries in asymmetric aldol reactions applied to total synthesis. Tetrahedron Asymmetry 24:1149–1188

    Google Scholar 

  • Jain AK, Vaidya A, Ravichandran V, Kashaw SK (2012) Recent developments and biological activities of thiazolidinone derivatives. Bioorg Med Chem 20:3378–3395

    Article  CAS  PubMed  Google Scholar 

  • Jiang S, Tala SR, Lu H et al (2011) Design, synthesis, and biological activity of novel 5-((Arylfuran/1H-pyrrol-2-yl)methylene)-2-thioxo-3-(3-(trifluoromethyl)phenyl)thiazolidin-4-ones as HIV-1 fusion inhibitors targeting gp41. J Med Chem 54:572–579

    Article  CAS  PubMed  Google Scholar 

  • Kalhor M, Banibairami S, Mirshokraie SA (2018) Ni@zeolite-Y nanoporous; a valuable and efficient nanocatalyst for the synthesis of N-benzimidazole-1,3-thiazolidinones. Green Chem Lett Rev 11:334–344

    Article  CAS  Google Scholar 

  • Kalhor M, Banibairami S (2020) Design of a new multifunctional catalytic system Ni/SO3H@zeolite-Y for three-component synthesis of N-benzo-imidazo- or -thiazole-1,3-thiazolidinones. RSC Adv 10:41410–41423

    Article  CAS  Google Scholar 

  • Kerr DJ, Miletic M, Chaplin JH et al (2012) Oxazolidinone-promoted, torquoselective nazarov cyclizations. Org Lett 14:1732–1735

    Article  CAS  PubMed  Google Scholar 

  • Leonelli C, Mason TJ (2010) Microwave and ultrasonic processing: now a realistic option for industry. Chem Eng Process 49:885–900

    Article  CAS  Google Scholar 

  • Li X, Xia D, Wen Z et al (2018) Magnetic magnetite nanoparticals catalyzed selective oxidation of αhydroxy ketones with air and one-pot synthesis of benzilic acid and phenytoin derivatives. Mol Catal 454:63–69

    Google Scholar 

  • Liu X, Li J, Wang R (2017) Desulfurization and regeneration performance of heteropoly compound/ionic liquid solutions at high temperature. Chem Eng J 316:171–178

    Article  CAS  Google Scholar 

  • Ma L, Xie C, Ma Y, Liu J et al (2011) Synthesis and biological evaluation of novel 5-Benzylidenethiazolidine-2,4-dione derivatives for the treatment of inflammatory diseases. J Med Chem 54:2060–2068

    Article  CAS  PubMed  Google Scholar 

  • Manjal SK, Kaur R, Bhatia R, Kumar K, Singh V, Shankar R, Kaur R et al (2017) Synthetic and medicinal perspective of thiazolidinones. Bioorg Chem 75:406–423

    Google Scholar 

  • Manjal SK, Kaur R, Bhatia R, Kumar K et al (2017b) Synthetic and medicinal perspective of thiazolidinones: a review. Bioorg Chem 75:406–423

    Google Scholar 

  • Meireles ALP, da Silva Rocha KA, Kozhevnikova EF et al (2018) Heteropoly acid catalysts for the valorization of biorenewables: Isomerization of caryophyllene oxide in green solvents. Mol Catal 458:213–222

    Article  CAS  Google Scholar 

  • Mendgen T, Steuer C, Klein CD (2012) Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry. J Med Chem 55:743–753

    Article  CAS  PubMed  Google Scholar 

  • Mobinikhaledi A, Foroughifar N, Kalhor M, Mirabolfathy M (2010) Synthesis and antifungal activity of novel 2-benzimidazolylimino-5-arylidene-4-thiazolidinones. J Heterocycl Chem 47:77–80

    CAS  Google Scholar 

  • Moreira DRM, Costa SPM, Hernandes MZ, Rabello MM, Oliveria Filho GB et al (2012) Structural investigation of anti-trypanosoma cruzi 2-Iminothiazolidin-4-ones allows the identification of agents with efficacy in infected mice. J Med Chem 55:10918–10936

    Article  CAS  PubMed  Google Scholar 

  • Mozafari R, Heidarizadeh F, Nikpour F (2019) MnFe2O4 magnetic nanoparticles modified with chitosan polymeric and phosphotungstic acid as a novel and highly effective green nanocatalyst for regio- and stereoselective synthesis of functionalized oxazolidin-2-ones. Mater Sci Eng 105:110109

    Google Scholar 

  • Murugesan V, Prabhakar YS, Seturam B et al (2009) CoMFA and CoMSIA studies on thiazolidin-4-one as anti-HIV-1 agent. J Mol Graph Model 27:735–743

    Article  CAS  PubMed  Google Scholar 

  • Nanjan MJ, Kumar BRP, Chandrasekar MJN (2018) Thiazolidinediones as antidiabetic agents: acritical review. Bioorg Chem 77:458–567

    Article  CAS  Google Scholar 

  • Narayanaswamy K, Swetha T, Kapil G et al (2015) Simple metal-free dyes derived from Triphenylamine for DSSC: a comparative study of two different anchoring group. Electrochim Acta 169:256–263

    Article  CAS  Google Scholar 

  • Naresh M, Venkateswara Rao SS, Kotapalli R et al (2014) Oxazolidinone derivatives: Cytoxazone-Linezolid hybrids induces apoptosis and senescence in DU145 prostate cancer cells. Eur J Med Chem 80:295–307

    Article  CAS  PubMed  Google Scholar 

  • Nasibullah M, Hassan F, Ahmad N et al (2015) Recent developments in oxazolidinones as potent antibacterials. Adv Sci Eng Med 7:91–111

    Article  CAS  Google Scholar 

  • Osmaniye D, Levent S, Ardıç CM et al (2017) Synthesis and anticancer activity of some novel benzothiazole-thiazolidine derivatives. Phosphorus Sulfur Silicon Relat Elem 193:249–256

    Article  CAS  Google Scholar 

  • Pagadala R, Maddila S, Jonnalagadda SB (2014) Eco-efficient ultrasonic responsive synthesis of pyrimidines/pyridines. Ultrason Sonochem 21:472–477

    Article  CAS  PubMed  Google Scholar 

  • Reddy RS, Chouthaiwale PV, Suryavanshi G et al (2010) Co(iii)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S, S)-reboxetine and (+)-epi-cytoxazone. Chem Commun 46:5012–5014

    Article  CAS  Google Scholar 

  • Ren W, Liu Y, Lu X (2014) Bifunctional aluminum catalyst for CO2 fixation: regioselective ring opening of three-membered heterocyclic compounds. J Org Chem 79:9771–9777

    Article  CAS  PubMed  Google Scholar 

  • Rostamnia S, Doustkhah E, Nuri A (2013) Hexafluoroisopropanol dispersed into the nanoporous SBA-15 (HFIP/SBA-15) as a rapid, metal-free, highly reusable and suitable combined catalyst for domino cyclization process in chemoselective preparation of alkyl rhodanines. J Fluorine Chem 153:1–6

    Article  CAS  Google Scholar 

  • Rostamnia S, Zeynizadeh B, Doustkhah E et al (2015) The use of κ-Carrageenan/Fe3O4 nanocomposite as a nanomagnetic catalyst for clean synthesis of rhodanines. Catal Commun 68:77–83

    Article  CAS  Google Scholar 

  • Sadeghzadeh SM, Daneshfar F (2014) Ionic liquid immobilized on FeNi3 as catalysts for efficient, green, and one-pot synthesis of 1,3-thiazolidin-4-one. J Mol Liq 199:440–444

    Article  CAS  Google Scholar 

  • Safaei-Ghomi J, Javidan A, Ziarati A et al (2015) Synthesis of new 2-amino-4H-pyran-3,5-dicarboxylate derivatives using nanocrystalline MIIZr4(PO4)6 ceramics as reusable and robust catalysts under microwave irradiation. J Nanopart Res 17:338–350

    Article  CAS  Google Scholar 

  • Safaei-Ghomi J, Navvab M, Shahbazi-Alavi H (2016a) One-pot sonochemical synthesis of 1,3-thiazolidin-4-ones using nano-CdZr4(PO4)6 as a robust heterogeneous catalyst. Ultrasonics Sonochem 31:102–106

    Google Scholar 

  • Safaei-Ghomi J, Nazemzadeh SH, Shahbazi-Alavi H (2016b) Nano-CdZr4(PO4)6 as a reusable and robust catalyst for the synthesis of bis-thiazolidinones by a multicomponent reaction of aldehydes, ethylenediamine and thioglycolic acid. J Sulfur Chem 38:195–205

    Google Scholar 

  • Safaei-Ghomi J, Navvab M, Shahbazi-Alavi H. (2016c) CoFe2O4@SiO2/PrNH2 nanoparticles as highly efficient and magnetically recoverable catalyst for the synthesis of 1,3-thiazolidin-4-ones. J Sulfur Chem 37:601–612

    Google Scholar 

  • Safaei-Ghomi J, Bakhtiari A (2019) Tungsten anchored onto functionalized SBA-15: an efficient catalyst for diastereoselective synthesis of 2-azapyrrolizidine alkaloid scaffolds. RSC Adv 9:19662–19674

    Article  CAS  Google Scholar 

  • Sankar PS, Divya K, Padmaja A, Padmavathi V (2017) Synthesis and antimicrobial activity of azetidinone and thiazolidinone derivatives from azolylindolyl Schiff’s bases. Med Chem 7:340–347

    Article  Google Scholar 

  • Sivanadanam J, Mukkamala R, Mandal S et al (2018) Exploring the role of the spacers and acceptors on the triphenylamine-based dyes for dye-sensitized solar cells. Int J Hydrogen Energy 43:4691–4705

    Article  CAS  Google Scholar 

  • Srivastava T, Haq W, Katti SB (2002) Carbodiimide mediated synthesis of 4-thiazolidinones by one-pot three-component condensation. Tetrahedron 58:7619–7624

    Article  CAS  Google Scholar 

  • Tanabe K, Hölderich WF (1999) Industrial application of solid acid-base catalysts. Appl Catal 181:399–434

    Article  CAS  Google Scholar 

  • Vavsari V, Mohammadi Ziarani G, Balalaie S et al (2016) New functionalized 8-hydroxyquinoline-5-sulfonic acid mesoporous silica (HQS-SBA-15) as an efficient catalyst for the synthesis of 2-thiohydantoin derivatives. Tetrahedron 72:5420–5426

    Article  CAS  Google Scholar 

  • Vengurlekar S, Sharma R, Trivedi T (2012) A study on the biological activity of 2-thioxo-imidazolidin-4-ones. Lett Drug Des Discov 9:549–555

    Article  CAS  Google Scholar 

  • Watile RA, Bagal DB, Patil YP et al (2011) Regioselective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines using Br−Ph3+PPEG600P+Ph3Br− as an efficient, homogenous recyclable catalyst at ambient conditions. Tetrahedron Lett 52:6383–6387

    Article  CAS  Google Scholar 

  • Yang X, Bumbu VD, Liu P, Li X et al (2012) Catalytic, enantioselective N-Acylation of lactams and thiolactams using amidine-based catalysts. J Am Chem Soc 134:17605–17612

    Article  CAS  PubMed  Google Scholar 

  • Yuan B, Li Y, Wang Z et al (2017) A Novel Brønsted-Lewis acidic catalyst based on heteropoly phosphotungstates: synthesis and catalysis in benzylation of p-xylene with benzyl alcohol. Mol Catal 443:110–116

    Article  CAS  Google Scholar 

  • Zehetmeyr FK, Pereira da Silva MAM, Pereira KM et al (2018) Ovicidal in vitro activity of 2-aryl-3-(2-morpholinoethyl)thiazolidin-4-ones and 2-aryl-3-(3-morpholinopropyl)thiazolidin-4-onesagainst Fasciola hepatica (Linnaeus, 1758). Exp Parasitol 192:60–64

    Article  CAS  PubMed  Google Scholar 

  • Zhang Q, Zhou H, Zhai S et al (2010) Natural product-inspired synthesis of thiazolidine and thiazolidinone compounds and their anticancer activities. Curr Pharm Des 16:1826–1842

    Article  CAS  PubMed  Google Scholar 

  • Zhang L, Dong WF, Sun HB (2013) Multifunctional superparamagnetic iron oxide nanoparticles: design, synthesis and biomedical photonic applications. Nanoscale 5:7664–7684

    Article  CAS  PubMed  Google Scholar 

  • Ziarati A, Safaei-Ghomi J, Rohani S (2013) Sonochemically synthesis of pyrazolones using reusable catalyst CuI nanoparticles that was prepared by sonication. Ultrason Sonochem 20:1069–1075

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Koç University Tüpraş Energy Center (KUTEM), Department of Chemistry, Koç University, Istanbul, 34450, Turkey

    Esmail Doustkhah

  2. Research Department of Chemistry, Iranian Academic Center for Education, Culture and Research, Urmia, Iran

    Fatemeh Majidi Arlan

Authors
  1. Esmail Doustkhah
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  2. Fatemeh Majidi Arlan
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Editor information

Editors and Affiliations

  1. Department of Chemistry, Mody University of Science and Technology, Lakshmangarh, India

    Keshav Lalit Ameta

  2. Chemistry, Shri Ramswaroop Memorial University, Lucknow, Uttar Pradesh, India

    Ravi Kant

  3. Chemistry, University of Insubria, Varese, Italy

    Andrea Penoni

  4. Science and High Technology, University of Insubria, Varese, Italy

    Angelo Maspero

  5. Science and High Technology, University of Insubria, Varese, Italy

    Luca Scapinello

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Doustkhah, E., Arlan, F.M. (2022). Synthesis of Bioactive Thioxoimidazolidinones, Oxazolidinones, Thioxothiazolidinones, Thiazolidinediones. In: Ameta, K.L., Kant, R., Penoni, A., Maspero, A., Scapinello, L. (eds) N-Heterocycles. Springer, Singapore. https://doi.org/10.1007/978-981-19-0832-3_13

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