Synthesis, Characterization and Antibacterial Activities of New Fluorinated Chalcones

Chemistry Africa - Tập 2 - Trang 47-55 - 2019
Kayode L. Amole1, Isaac A. Bello1, Adebayo O. Oyewale1
1Faculty of Physical Sciences, Department of Chemistry, Ahmadu Bello University, Zaria, Nigeria

Tóm tắt

A series of five fluorinated chalcones (E)-3-(2′-ethoxyphenyl)-1-(4-Fluoro-2-hydroxyphenyl)prop-2-en-1-one(4),(E)-3-(3′,4′-diethoxyphenyl)-1-(4-fluoro-2-hydroxyl-phenyl)prop-2-en-1-one(5),(E)-3-(2′,3′-dihydrobenzofuran-5-yl)-1-(4-Fluoro-2-hydroxylphenyl)prop-2-en-1-one(6),(E)-3-(3′,5′-Bis[trifluoromethyl]phenyl)-1-(4-Fluoro-2-hydroxylphenyl)prop-2-en-1-one(7) and (E)-3-(4′-diethylaminophenyl)-1-(4-Fluoro-2-hydroxylphenyl)prop-2-en-1-one(8) were synthesized by a modified Claisen-Schmidt condensation of 4-fluoro-2-hydroxyacetophenone with the appropriate aromatic aldehydes. The compounds were characterized by spectroscopic methods and evaluated for their antibacterial activity against Gram-positive (Methicillin-resistant S. aureus, Vancomycin-resistant enterococci, S. aureus, S. pyrogenes, S. faecalis) and Gram-negative (E. coli, S. typhi, C. ulcerans, P. mirabilis, P. aeruginosa) pathogenic bacteria strains using the agar diffusion method. The compounds exhibited broad spectrum activity against eight of these pathogens with compounds (4), (5) and (8) found to be the most potent in the series with zones of inhibition ranging from 23 to 28 mm and MIC between 25 and 50 µg/mL. All the compounds except (7) containing 3-(3′,5′-bis[trifluoromethyl]phenyl) moiety, showed a remarkable activity against MRSA [MIC = 25–50 µg/mL]. Compound (8) exhibited good activity against P. aeruginosa [MIC = 50 µg/mL]. Compounds (4), (5) and (8) were active against C. ulcerans [MIC = 50 µg/mL]. The broad-spectrum standard drug, ciprofloxacin, was inactive against MRSA, P. aeruginosa and C. ulcerans.

Tài liệu tham khảo

Ghorab MM, Alsaid MS, El-Gaby MSA, Elaasser MM, Nissan YM (2017) Antimocrobial and anticancr activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties, synthesis, biological evaluation and molecular docking. Chem Cent J 11:32–35

Shah P, Westwell AD (2007) Review article: the role of fluorine in medicinal chemistry. J Enzyme Inhib Med Chem 22(5):527–540

Hu JJ, Zeng Y (2015) Recent advances in green fluorine chemistry. Rep Org Chem 5:19–39

Isabor C, O’Hagan D (2006) Fluorine in medicinal chemistry: a review of anticancer agents. J Fluo Chem 127:303–319

Kirk KL (2006) Fluorine in medicinal chemistry: recent application of fluorinated small molecules. J Fluo Chem 127:1013–1029

Murphy CD (2016) Microbial degradation of fluorinated drugs: biochemical pathway, impacts in the environment and potential application. Appl Microbiol 100(6):2617–2627

Abdellatif KRA, Elshemy HA, Salama SA, Omar HA (2015) Synthesis, characterization and biological evaluation of novel 4-fluoro-2-hydroxychalcone derivatives as antioxidant, anti-inflammatory, analgestic agents. J Enzyme Inhib Med Chem 30(3):484–491

Hasan SA, Elias AN, Jwaied AH, Khuodaer AR, Hussain SA (2012) Synthesis of new flourinated derivative with anti-inflammatory activity. Int J Pharm Sci 4(5):430–434

Nakamura C, Kawasaki N, Miyataka H, Jayachandran E, Kim IHJ, Kirk KL, Taguchi T, Takeuchi Y, Hori H, Satoh T (2002) Synthesis and biological activities of fluorinated chalcone derivatives. Bioorg Med Chem Lett 10:699–706

Liu M, Walairat P, Go M (2001) Antimalarial alkoxylated and hydroxylated chalcones: structure-activity relationship analysis. J Med Chem 44:4443–4452

Padhye S, Ahmed A, Oswal N, Dandawate P, Rub RA, Deshpande J, Swamy KV, Sarkar FH (2010) Fluorinated 20-hydroxychalcones as garcinol analogs with enhanced antioxidant and anticancer activities. Bioorg Med Chem Lett 20:5818–5821

Tiwari B, Pratapwar AS, Tapas AR, Butle SR, Vatkar BS (2010) Synthesis and antimicrobial activity of some chalcone derivatives. Int J Chem Tech Res 2(1):499–503

Amole KL, Bello IA, Oyewale AO (2018) Synthesis, characterization and antifungal study of five new derivatives of E-1-(2-Hydroxyphenyl)chalcone. Chem Afr. https://doi.org/10.1007/s42250-018-0027-3

Lino A, Deogracios O (2006) The in vitro anti- bacterial activity of Annona senegalensis, Securidacca longipendiculata and Steanotaenia araliacea. Afr J Health Sci 1(6):31–35

Vollekova A, Kostalova S, Sochorova R (2001) Iso-quinoline Alkaloids from Mahonia aquifolium stem bark is active against Malassezia Sp. Folia Microbiol 46:107–111

Usama H, Abdulrahman FT, Ladan AA (2007) Phytochemical and evaluation of tribulus terrestris L. (Zygophyllaceae) growing in Nigeria. Res J Biol Sci 2(3):244–247

Wesley, G. L. O. (2013). Synthesis, characterization and antioxidant activity of prenylated and fluorinated based flavonoids. MSc Thesis, University of Kwazulu-Natal, South Africa

Burmaoglu S, Algul O, Gobek A, Anil DK, Ulger M, Erturk BG, Kaplan E, Aslan G (2017) Design of potent fluoro-substituted chalcones as antimicrobial agents. J Enzyme Inhib Med Chem 3(1):490–495

Yadav P, Lal K, Kumar L, Kumar A, Paul AV, Kumar R (2018) Synthesis, crystal structure and antimicrobial potential of some fluorinated chalcones-1,2,3-triazole conjugates. Eur J Med Chem 155:263–274

Prasad YR, Rao AL, Rambabu RE (2008) Synthesis and antimicrobial activity of some chalcone derivatives. E-J Chem 5(3):461–466

Kamboj RC, Arora R, Sharma G, Kumar D, Sharma C, Joshi R, Aneja KR (2010) Ecofriendly synthesis and antimicrobial activity of chalcones. Der pharma Chem. 2(3):157–170

Ibrahim NS, Ahmed F (2014) Antimicrobial activities of some synthetic flavonoids. J App Chem 7(5):01–06

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Chemistry Africa

Tập 2

47-55

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