Skip to main content

Advertisement

SpringerLink
Log in

In vitro antimicrobial and antimycobacterial activity of some chalcones and their derivatives

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

Abstract

In this study, novel series of chalcone derivatives, namely, 4-[4-(3-phenyl-acryloyl)-phenylamino]-chromen-2-one (5a–k) have been synthesized from the intermediate 4-(4-acetyl-phenylamino)-chromen-2-one (4). Cyclization reaction of chalcone (5a–k) with hydrazine hydrate, guanidine nitrate, and malononitrile gives the corresponding 4-[4-(1-acetyl-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-phenylamino]-chromen-2-one (6a–k), 4-[4-(2-amino-6-phenyl-pyrimidin-4-yl)-phenylamino]-chromen-2-one (7a–k), and 2-amino-6-[4-(2-oxo-2H-chromen-4-ylamino)-phenyl]-4-phenyl-nicotinonitrile (8a–k) derivatives were synthesized. The newly synthesized compounds were evaluated for their antimycobacterial activity and antimicrobial activity against eight bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, and S. flexneri) and four fungi (A. niger, C. albicans, A. fumigatus, and A. clavatus).

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

  • Al-Soud YA, Al-Masoudi IA, Saeed B, Beifuß U, Al-Masoudi NA (2006) Synthesis of new 1H-1,2,4-triazolylcoumarins and their antitumor and anti-HIV activities. Chem Heterocycl Compd 42:583–590

    Article  CAS  Google Scholar 

  • Amit RT, Dipti KD, Naresh RR, Viresh HS (2008) Synthesis and biological evaluation of new pyrimidines via a novel chalcone series. Arkivoc 11:131–141

    Google Scholar 

  • Anjani S, Kishor K, Ana C, Marina S, Irini D, Athina G (2010) Synthesis of some new s-triazine based chalcones and their derivatives as potent antimicrobial agents. Eur J Med Chem 45:510–518

    Article  Google Scholar 

  • Anto RJ, Sukumaran K, Kuttana G, Rao MNA, Subbaraju V, Kuttana R (1995) Anticancer and antioxidant activity of synthetic chalcones and related compounds. Cancer Lett 97:33–37

    Article  PubMed  CAS  Google Scholar 

  • Babasaheb PB, Shrikant SG, Ragini GB, Nalini MG, Chandrahasya NK (2009) Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents. Bioorg Med Chem 17:8168–8173

    Article  Google Scholar 

  • Bedoya LM, Beltrán M, Sancho R, Olmedo DA, Sánchez-Palomino S, del Olmo E, López-Pérez JL, Muñoz E, San Feliciano A, Alcamí J (2005) 4-Phenylcoumarins as HIV transcription inhibitors. Bioorg Med Chem Lett 15:4447–4450

    Article  PubMed  CAS  Google Scholar 

  • Belluti F, Fontana G, Dal Bo L, Carenini N, Giommarelli C, Zunino F (2010) Design, Synthesis and anticancer activities of stilbene-coumarin hybrid compounds: Identification of novel proapoptotic agents. Bioorg Med Chem 18:3543–3550

    Article  PubMed  CAS  Google Scholar 

  • Bhat BA, Dhar KL, Puri SC, Saxena AK, Shanmugavel M, Qazi GN (2005) Synthesis and biological evaluations of chalcones and their derived pyrazoles as potential cytotoxic agents. Bioorg Med Chem Lett 15:3177–3180

    Article  PubMed  CAS  Google Scholar 

  • Divyesh P, Rahul P, Premlata K, Navin P (2011) In vitro antimicrobial assessment of coumarin-based s-triazinyl piperazines. Med Chem Res. doi:10.1007/s00044-011-9676-3

  • Gillespie SH (1994) Medical microbiology-illustrated. Butterworth Heinemann Ltd., United Kingdom, pp 234–247

    Google Scholar 

  • Hawkey PM, Lewis DA (1994) Medical bacteriology—a practical approach. Oxford University Press, United Kingdom, pp 181–194

    Google Scholar 

  • Hsu YL, Kuo PL, Tzeng WS, Lin CC (2006) Chalcone inhibits the proliferation of human breast cancer cell by blocking cell cycle progression and inducing apoptosis. Food Chem Toxicol 44:704–713

    Article  PubMed  CAS  Google Scholar 

  • Hussain M, Hussain MT, Rama NH, Hameed S, Malik A, Khan KM (2003) Synthesis and antimicrobial activities of some isocoumarin and dihydroisocoumarin derivatives. Nat Prod Res 17:207–214

    Article  PubMed  CAS  Google Scholar 

  • Isenberg HD (1992) Clinical microbiology procedures handbook, vol 1. American Society for Microbiology, Washington, DC

    Google Scholar 

  • Khalid MK, Zafar SS, Muhammad ZK, Zia-Ullah, Iqbal Choudhary M, Atta-ur-Rahman, Shahnaz P, Zahid HC, Claudiu TS (2004) Synthesis of coumarin derivatives with cytoxic, antibacterial and antifungal activity. J Enzyme Inhib Med Chem 19:373–379

    Article  Google Scholar 

  • Kishor HC, Mayank JP, DHaval BV (2008) Design, synthesis and evaluation of novel quinolyl chalcones as antibacterial agents. Arkivoc 13:189–197

    Google Scholar 

  • Koneni VS, Manoj K, Ram KM, Ravi S, Gitika B, Khanna Ak, Shivika R, Rakesh S (2011) Synthesis and anti-inflammatory activity of novel biscoumarin–chalcone hybrids. Bioorg Med Chem Lett 21:4480–4484

    Article  Google Scholar 

  • Kostova I, Bhatia S, Grigorov P, Balkansky S, Parmar VS, Prasad AK, Saso L (2011) Coumarins as antioxidants. Curr Med Chem 18:3929–3951

    Article  PubMed  CAS  Google Scholar 

  • Kováč M, Sabatié A, Floch Ľ (2001) Synthesis of coumarin sulfonamides and sulfonylurea. Arkivoc 6:100–108

    Google Scholar 

  • Laughon BE (2007) New tuberculosis drugs in development. Curr Top Med Chem 7:463–467

    Article  PubMed  CAS  Google Scholar 

  • Lee SH, Seo GS, Kim JY, Jin XY, Kim HD, Sohn DH (2006) Heme oxygenase 1 mediates anti-inflammatory effects of 2′,4′,6′-tris(methoxymethoxy) chalcone. Eur J Pharmacol 532:178–186

    Article  PubMed  CAS  Google Scholar 

  • Liu M, Wilairat P, Croft SL, Tan AL, GO M (2003) Structure-activity relationship of anti-leishmanial and antimalarial chalcones. Bioorg Med Chem 11:2729–2738

    Article  PubMed  CAS  Google Scholar 

  • López SN, Castelli MV, Zacchino SA, Domínguez JN, Lobo G, Charris-Charris J, Cortés JC, Ribas, Devia C, Rodríguez AM, Enriz RD (2001) In vitro antifungal evaluation and structure–activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall. Bioorg Med Chem 9:1999–2013

    Article  PubMed  Google Scholar 

  • Manolov I, Danchev ND (1995) Synthesis, toxicological and pharmacological assessment of some 4-hydroxycoumarin. Eur J Med Chem 30:531–536

    Article  CAS  Google Scholar 

  • Nida NF, Mudasir RB, Anis A, Asad UK, Abdul R (2011) 7-Hydroxy-coumarin derivatives: synthesis, characterization and preliminary antimicrobial activities. Med Chem Res 20:535–541

    Article  Google Scholar 

  • Nitin K, Alka C, Sushma D (2011) Synthesis of cyanopyridine and pyrimidine analogues as new anti-inflammatory and antimicrobial agents. Biomed Pharmacother 65:375–380

    Article  Google Scholar 

  • Nowakowska Z (2007) A review of antiinfective and anti-inflammatory chalcones. Eur J Med Chem 42:125–137

    Article  PubMed  CAS  Google Scholar 

  • Tenover FC, McDonald LC (2005) Vancomycin-resistant staphylococci and enterococci: epidemiology and control. Curr Opin Infect Dis 18:300–305

    Article  PubMed  CAS  Google Scholar 

  • Tomar V, Bhattacharjee G, Kamaluddin, Kumar A (2007) Synthesis and antimicrobial evaluation of new chalcones containing piperazine or 2,5-dichlorothiophene moiety. Bioorg Med Chem Lett 17:5321–5324

    Article  PubMed  CAS  Google Scholar 

  • Yi X, Zheng-Yu Y, Peng X, Kenneth FB, Yuka N, Kuo-Hsiung L (2000) Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation. Bioorg Med Chem Lett 10:699–701

    Article  Google Scholar 

  • Zhang Y, Shi S, Zhao M, Jiang Y, Tu P (2006) A novel chalcone from Coreopsis tinctoria nutt. Biochem Syst Ecol 34:766–769

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Applied Chemistry, S.V. National Institute of Technology, Surat, 395007, India

    Divyesh Patel & Premlata Kumari

  2. Department of Chemistry, V.N. South Gujarat University, Surat, 395007, India

    Navin B. Patel

Authors
  1. Divyesh Patel
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Premlata Kumari
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Navin B. Patel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Premlata Kumari.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Patel, D., Kumari, P. & Patel, N.B. In vitro antimicrobial and antimycobacterial activity of some chalcones and their derivatives. Med Chem Res 22, 726–744 (2013). https://doi.org/10.1007/s00044-012-0073-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-012-0073-3

Keywords

Search

Navigation