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Published on:December 2017
Indian Journal of Pharmaceutical Education and Research, 2017; 51(4s):s679-s690
Original Article | doi:10.5530/ijper.51.4s.99

Synthesis and Biological Activity of Novel 2,5-Dichloro-3-Acetylthiophene Chalcone Derivatives


Authors and affiliation (s):

Bontha Venkata Subrahmanya Lokesh1*, Yejella Rajendra Prasad2, Afzal Basha Shaik3

1Faculty of Pharmaceutical Sciences, UCSI University, Kuala Lumpur, MALAYSIA.

2College of Pharmaceutical Sciences, Andhra University, Visakhapatnam, INDIA.

3Vignan Pharmacy College, Guntur, INDIA.

Abstract:

Objective: A series of novel 2, 5-dichloro-3-acetylthiophene chalcone derivatives were synthesized by Claisen-Schmidt condensation and evaluated for them in vitro antifungal, antitubercular activities and cytotoxic activity against DU145 (prostate) cancer cell line. Methods: Among all series of synthesized compounds, four compounds were displayed proximity of antifungal activity (MIC ≤ 8.0 μg/mL) towards the fungus species Aspergillus niger (ATCC 6275, An) and Candida tropicalis (ATCC 1369, Ct) and compared against fluconazole standard (MIC ≤ 1.0 μg/mL) by agar-diffusion and tube dilution methods. Results: One compound was shown a promising antimycobacterial activity (MIC∼3.12 μg/mL) correlated with pyrazinamide (MIC∼3.12 μg/mL) and also another five compounds exhibited better activity (MIC∼6.25 μg/mL) towards M. tuberculosis H37Rv species. All series of compounds were treated with DU145 cells and tested for cytotoxicity by MTT assay. Among all, one compound was shown similar cytotoxicity activity (IC50 ∼5±1 μg/ mL) and the other compound was shown closer activity (IC50∼10±2μg/mL) compared with a methotrexate (IC50 ∼5±1 μg/mL). The spectral studies (FT-IR, Mass, 1HNMR and 13CNMR) studies provided new molecular scaffolds with detailed structure-activity relationship. Conclusion: These novel chalcones with thienyl ring structure would be promising new scaffold for establishing specific targets on fungal, mycobacteria species and other cancer cell lines.

Key words: 2, 5-Dichloro-3-acetylthiophene chalcone derivatives, Claisen-Schmidt condensation, Cytotoxic activity, DU145 (prostate) cancer cell line, Structure-activity relationship, Antifungal activity, Antitubercular activity.

 

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The Official Journal of Association of Pharmaceutical Teachers of India (APTI)
(Registered under Registration of Societies Act XXI of 1860 No. 122 of 1966-1967, Lucknow)

Indian Journal of Pharmaceutical Education and Research (IJPER) [ISSN-0019-5464] is the official journal of Association of Pharmaceutical Teachers of India (APTI) and is being published since 1967.

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IJPER uses reference linking service using Digital Object Identifiers (DOI) by Crossref. Articles from the year 2013 are being assigned DOIs for its permanent URLs