Skip to main content

Advertisement

SpringerLink
Log in

New thiazolidinedione-5-acetic acid amide derivatives: synthesis, characterization and investigation of antimicrobial and cytotoxic properties

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

The present work describes the synthesis, antimicrobial and cytotoxic activity of 2,4-thiazolidinedione-5-acetic acid amides 3a–n. The structures of the compounds were confirmed by IR, 1H, 13C NMR and elemental analysis. All compounds were tested for antimicrobial activity by twofold serial dilution technique. The preliminary results revealed that the compound 3d exhibits promising antibacterial and antifungal activity. The cytotoxic (MTT) activity of 2,4-thiazolidinedione-5-acetic acid amides were tested in four tumour cell lines. We found that compound 3j inhibited proliferation of HeLa, HT29, A549 and MCF-7 cell lines with IC50 values of 33, 35, 30 and 36 μM, respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1

Similar content being viewed by others

References

  • Andreani A, Rambaldi M, Locatelli A, Leoin A, Bossa R, Chiericozzi M, Galatulas I, Salvatore G (1993) Synthesis of lactams with potential cardiotonic activity. Eur J Med Chem 28:825–829

    Article  CAS  Google Scholar 

  • Ayhan-kilcigil G, Altanlar N (2000) Synthesis of 3-substituted phenacyl-5-[2-phenyl-4H–4-oxo-1-benzopyran-6-yl-methylenyl]-thiazolidine-2, 4-dione and their antimicrobial activity. Arzneimittelforschung 50:154–157

    PubMed  CAS  Google Scholar 

  • Boschelli DH, Connor DT, Kuipers PJ, Wright CD (1992) Synthesis and cyclooxygenase and 5-lipoxygenase inhibitory activity of some thiazolidine-4-one analogs of meclofenamic acid. Bioorg Med Chem Lett 2:705–708

    Article  CAS  Google Scholar 

  • Boyd AS (2007) Thiazolidinedione in dermatology. Int J Dermatol 46:557–563

    Article  PubMed  CAS  Google Scholar 

  • Bozdag-Dundar O, Ozgen O, Mentese A, Altanlar N, Ath O, Kendi E, Ertan R (2007) Synthesis and antimicrobial activity of some new thiazolil thiazolidine-2,4-dione derivatives. Bioorg Med Chem 15:6012–6017

    Article  PubMed  Google Scholar 

  • DeLima JG, Perrissin M, Chantegrel J (1994) Synthesis and pharmacological evaluation of some 3-phenacyl-5-benzylidene-thiazolidine-2,4-diones. Arzneimittelforschung 44:831–834

    CAS  Google Scholar 

  • Elte JWF, Blickle JF (2007) Thiazolidinedione for the treatment of type 2 diabetes. Eur J Inter Med 18:18–25

    Article  CAS  Google Scholar 

  • Farghaly AA, Bekhit AA, Park JY (2000) Design and synthesis of some oxadiazolyl, thiazolidinyl and thiazolyl derivatives of 1H-pyrazole as anti-inflammatory and antimicrobial agents. Arch Pharm Pharm Med Chem 333:53–57

    Article  CAS  Google Scholar 

  • Foroumadi A, Emami S, Hassanzadeh A, Rajaee M, Sokhanvar K, Moshafi MH, Shafiee A (2005a) Synthesis and antibacterial activity of N-(5-benzylthio-1,3,4-thiadiazole-2-yl) and N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl)piperazinyl quinolone derivatives. Bioorg Med Chem Lett 15:4488–4492

    Article  PubMed  CAS  Google Scholar 

  • Foroumadi A, Emami S, Pournourmohammadi S, Kharazmi A, Shafiee A (2005b) Synthesis and in vitro leishmanicidal activity of 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-5-substituted-1,3,4-thiadiazole derivatives. Eur J Med Chem 40:1346–1350

    Article  PubMed  CAS  Google Scholar 

  • Foroumadi A, Soltani F, Moallemzadeh-Haghighi H, Shafiee A (2005c) Synthesis, in-vitro-antimycobacterial activity and cytotoxicity of some alkyl α-(5-aryl-1,3,4-thiadiazole-2-ylthio)acetates. Arch Pharm Chem Life Sci 338:112–116

    Article  CAS  Google Scholar 

  • Grange JM, Zumla A (2002) The global emergency of tuberculosis: what is the cause? J R Soc Health 122:78–81

    Article  CAS  Google Scholar 

  • Heerding DA, Cristmann LT, Clark TJ, Holmes DJ, Rittenhouse SF, Takata DT, Venslavsky JW (2003) New benzylidenethiazolidinedione as antibacterial agents. Bioorg Med Chem Lett 13:3771–3773

    Article  PubMed  CAS  Google Scholar 

  • Heneka MT, Landreth GE (2007) PPARs in the brain. Biochim Biophys Acta 1771:1031–1045

    PubMed  CAS  Google Scholar 

  • Jiang C, Ting AT, Seed B (1998) PPAR-gamma agonists inhibit production of monocyte inflammatory cytokines. Nature 391:82–86

    Article  PubMed  CAS  Google Scholar 

  • Kadi AA, El-Brollosy NR, Al-Deeb OA, Habib EE, Ibrahim TM, El-Emam AA (2007) Synthesis, antimicrobial, and anti-inflammatory activites of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazole and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. Eur J Med Chem 42:235–242

    Article  PubMed  CAS  Google Scholar 

  • Kalaitzidis RG, Sarafidis PA, Bakeis GL (2009) Effects of thiazolidinedione beyond glycaemic control. Curr Pharm Des 15:529–536

    Article  PubMed  CAS  Google Scholar 

  • Kurebayashi S, Xu X, Ishii S, Shirashi M, Kouhara H, Kasayama S (2005) A novel thiazolidinedione MCC-555 down-regulates tumor necrosis factor-α-induced expression of vascular cell adhesion molecule-1 in vascular endothelial cells. Atherosclerosis 182:71–77

    Article  PubMed  CAS  Google Scholar 

  • Mamolo MG, Falagiani V, Zampieri D, Vio L, Banfi E, Scialino G (2003) Synthesis and antimycobacterial activity of (3,4-diaryl-3H-thiazol-2-ylidene)-hydrazide derivatives. IL Farmaco 58:631–637

    Article  PubMed  CAS  Google Scholar 

  • Mclntyre RS, Soczynska JK, Woldeyohannes HO, Lewis GF, Leiter LA, MacQueen GM, Miranda A, Fulgosi D, Konarski JZ, Kennedy SH (2007) Thiazolidinedione: noval treatments for cognitive deficits in mood disorders. Expert Opin Pharmacother 8:1615–1628

    Article  Google Scholar 

  • Modzelewska-Banachiewicz B, Banachiewicz J, Chodkowska A, Jagiello-Wojtowicz E, Mazur L (2004) Synthesis and biological activity of new derivatives of 3-(3,4-diaryl-1,2,4-triazole-5-yl)propenoic acid. Eur J Med Chem 39:873–877

    Article  PubMed  CAS  Google Scholar 

  • Mosmann T (1983) Rapid colorimetric assay for cellular growth and survrvial. Application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63

    Article  PubMed  CAS  Google Scholar 

  • National Committee for Clinical Laboratory Standards (2000) Method for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard document M-7: A5. National Committee for Clinical Laboratory Standards, Villanova, PA

    Google Scholar 

  • Pallas 3.7.1.2 (2010) ADME-Tox software. CompuDrug International Inc, USA

  • Ricote M, Li AC, Willson TM, Kelly CJ, Glass CK (1998) The peroxisome proliferator-activated receptor-gamma is a negative regulator of macrophage activation. Nature 391:79–82

    Article  PubMed  CAS  Google Scholar 

  • Schenone S, Brullo C, Bruno O, Bondavalli F, Ranise A, Filippelli W, Rinaldi B, Capuano A, Falcone G (2006) New 1,3,4-thiadiazole derivatives endowed with analgesic and anti-inflammatory activity. Bioorg Med Chem 14:1698–1705

    Article  PubMed  CAS  Google Scholar 

  • Solak N, Rollas S (2006) Synthesis and antituberculosis activity of 2-(aryl-alkylamino)-5-(4-aminophenyl)-1,3,4-thiadiazoles and their Schiff bases. Arkivoc xii:173–181

    Google Scholar 

  • Takahashi T (1964) Spincoupling constants for methylene groups adjacent to carbonyl groups. Tetrhedron Lett 5:565–572

    Article  Google Scholar 

  • Tu GG, Li SH, Huang HM, Li G, Xiong F, Mai X, Zhu HW, Kuang BH, Xu WF (2008) Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold. Bioorg Med Chem 16:6663–6668

    Article  PubMed  CAS  Google Scholar 

  • Tuncbilek M, Altanlar N (2006) Synthesis of new-(substituted phenycyl)-5-[3-(4H-oxo-1-benzopyran-2yl)-benzylidene]-2,4-thiazolidinedione and their antimicrobial activity. Arch Pharm Chem Life Sci 339:213–216

    Article  CAS  Google Scholar 

  • Varvaresou A, Siatra-Papastaikoudi T, Tsotinis A, Tsantili-Kakoulidou A, Vamvakides A (1998) Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 2,2,4-triazole. Il Farmaco 53:320–326

    Article  PubMed  CAS  Google Scholar 

  • Zimenkovskii BS, Kutsyk RV, Lesyk RB, Matyichuk VS, Obushak ND, Klyufinska TI (2006) Synthesis and antimicrobial activity of 2,4-dioxothiazolidine-5-acetic acid amides. Pharm Chem J 40:303–306

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, KLE University’s College of Pharmacy, Belgaum, 590 010, Karnataka, India

    Shankar G. Alegaon & Kallanagouda R. Alagawadi

Authors
  1. Shankar G. Alegaon
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kallanagouda R. Alagawadi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shankar G. Alegaon.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Alegaon, S.G., Alagawadi, K.R. New thiazolidinedione-5-acetic acid amide derivatives: synthesis, characterization and investigation of antimicrobial and cytotoxic properties. Med Chem Res 21, 816–824 (2012). https://doi.org/10.1007/s00044-011-9598-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-011-9598-0

Keywords

Search

Navigation