Synthesis and biological evaluation of some 2-(3,5-dimethyl-1H-pyrazol-1- yl)-1-arylethanones: Antibacterial, DNA photocleavage, and anticancer activities

Vinod Kumar, Kamalneet Kaur, Deepkamal N. Karelia, Vikas Beniwal, Girish Kumar Gupta, Arun K. Sharma, Akhilesh Kumar Gupta

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

In continuation of our efforts to find new biologically active agents, regioselective synthesis of a series of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1- arylethanones 4a-k has been achieved under facile, extremely mild and greener reaction conditions with excellent yields. Moreover, one pot multicomponent reaction has also been reinvestigated under previously reported solvent conditions to prepare 4a-b and found that the reaction generates significant amount of side products. The chemical structures of 4a-k were established on the basis of a combined use of IR, NMR (1H, 13C) spectroscopy, mass spectrometry and elemental analysis. All the compounds were evaluated for their antibacterial, DNA photocleavage and anticancer activities. Among all, 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-(naphth-2-yl)ethanone 4j displayed good inhibitory profile against Escherichia coli and Staphylococcus aureus which was about 50% and 25% of the Ampicillin (standard drug), respectively. The compounds, 4a and 4f showed relatively moderate inhibition against Psuedomonas aeruginosa and E. coli. In DNA photocleavage study, compounds 4c and 4d were found to be highly active and completely degraded both forms of DNA (SC and OC), even at a very low concentration of 1 μg (4c) under irradiation of UV light. However, 4h and 4f resulted in complete DNA degradation at 30 μg concentration. Moreover, 4h showed fluorescence at 15 μg concentration and increased the intensity of both bands of DNA (SC and OC) as compared to control. On the other hand, to valorize the biological potential, the compounds were screened for their cytotoxic activity on colon (HCT116 and HT29), prostate (DU145), ovarian (SKOV3) and lung (A549) cancer cell lines. The compound 4j was found to be cytotoxic to all the cancer cell lines, except SKOV3, with more selectivity towards the colon cancer cell lines (HCT116, HT29) and A549 lung cancer cell line. On A549 lung cancer cell line, 4j and 4k exhibited similar potency as carboplatin in inhibiting cell viability.

Original languageEnglish (US)
Pages (from-to)267-276
Number of pages10
JournalEuropean Journal of Medicinal Chemistry
Volume81
DOIs
StatePublished - Jun 23 2014

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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