Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Antimicrobial Activities of Chalcones and Indole Derived from Acetyl Pyridines
Corresponding Author(s) : S. Santra
Asian Journal of Chemistry,
Vol. 30 No. 4 (2018): Vol 30 Issue 4
Abstract
In the present study, chalcones and indole bearing nitrogen containing heterocyclic ring such as pyridine ring have been synthesized and characterized by elemental analysis and spectral studies. Attempts were made to prepare chacones via condensation of 2-acetyl pyridines/3-acetyl pyridines/4-acetyl pyridines with substituted benzaldehydes in presence of a number of different inorganic and organic bases. Out of different bases methanolic sodium hydroxide was found best both in terms of rate of reaction and percentage of yield. Synthesized chalcones and indoles were purified by flash column chromatography under nitrogen pressure. Purity of the isolated compounds was checked by HPLC. Compounds with HPLC purity of more than 98 % have been characterized and reported. Synthesized chalcones were tested against the bacteria strains Staphylococcus aureus and E. coli with reference to the standard drug ciprofloxacin at the concentration 1 μg/mL. Synthesized chalcones were further tested against the fungal strains Aspergillus niger and Penicillium funiculosum with reference to the standard ketoconazole at the concentration 1 μg/mL.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- P. Singh, A. Anand and V. Kumar, Eur. J. Med. Chem., 85, 758 (2014); https://doi.org/10.1016/j.ejmech.2014.08.033.
- C. Zhuang, W. Zhang, C. Sheng, W. Zhang, C. Xing and Z. Miao, Chem. Rev., 117, 7762 (2017); https://doi.org/10.1021/acs.chemrev.7b00020.
- B.K. Sharma, S.C. Ameta and V.K. Dwivedi, Int. J. Chem. Sci., 12, 1121 (2014).
- S. Raghavan, P. Manogaran, B. Kalpattu Kuppuswami, G. Venkatraman and K.K. Gadepalli Narasimha, Med. Chem. Res., 24, 4157 (2015); https://doi.org/10.1007/s00044-015-1453-2.
- Z. Nowakowska, Eur. J. Med. Chem., 42, 125 (2007); https://doi.org/10.1016/j.ejmech.2006.09.019.
- S.L. Gaonkar and U.N. Vignesh, Res. Chem. Intermed., 43, 6043 (2017); https://doi.org/10.1007/s11164-017-2977-5.
- B.P. Bandgar, S.S. Gawande, R.G. Bodade, J.V. Totre and C.N. Khobragade, Bioorg. Med. Chem., 18, 1364 (2010); https://doi.org/10.1016/j.bmc.2009.11.066.
- A. Torres de Pinedo, P. Peñalver and J.C. Morales, Food Chem., 103, 55 (2007); https://doi.org/10.1016/j.foodchem.2006.07.026.
- V.J. Ram, A. Saxena, S. Srivastava and S. Chandra, Bioorg. Med. Chem. Lett., 10, 2159 (2000); https://doi.org/10.1016/S0960-894X(00)00409-1.
- G.A. Crosby, P.C. Wang and R.E. Wingard Jr., 4-(Dihydroxyhexoxy)-dihydrochalcone Sweeteners, US Patent 4204007A (1980).
- M.D. Carmen, G. Barrio, J.R. Barrio, G. Walker, A. Novelli and N.J. Leonard, J. Am. Chem. Soc., 95, 4891 (1973); https://doi.org/10.1021/ja00796a021.
- S.J. Buckman, K.J. Flanagan, J.D. Pera and L.A. Wienert, Organic Esters and Their Use as Ultraviolet Light Absorbers and as Heat Stabilizers, US Patent 3733297A (1973).
- G.J. Macdonald and S.R. Nohr, Light-Stabilized Dyestuff Compositions, EP 0854896B1 (2002).
- I. Karaman, H. Gezegen, M.B. Gurdere, A. Dingil and M. Ceylan, Chem. Biodivers., 7, 400 (2010); https://doi.org/10.1002/cbdv.200900027.
- T.T. Tochigi, K.N. Ichikaimachi, M.H. Utsunomiya, S.M. Wakayama, G. Imokawa and N. Takaishi, Novel Chalcone Derivatives and Ultraviolet Absorbers Comprising the Same, US Patent 4584190A (1986).
- V. Sharma, P. Kumar and D. Pathak, J. Heterocycl. Chem., 47, 491 (2010); https://doi.org/10.1002/jhet.349.
- N.K. Kaushik, N. Kaushik, P. Attri, N. Kumar, C.H. Kim, A.K. Verma and E.H. Choi, Molecules, 18, 6620 (2013); https://doi.org/10.3390/molecules18066620.
- S. Bonjar, S. Aghighi and N.A. Karimi, J. Biol. Sci., 4, 405 (2005).
- C. Perez, M. Paul and P. Bazerque, Acta. Biol. Med. Exp, 15, 113 (1990).
References
P. Singh, A. Anand and V. Kumar, Eur. J. Med. Chem., 85, 758 (2014); https://doi.org/10.1016/j.ejmech.2014.08.033.
C. Zhuang, W. Zhang, C. Sheng, W. Zhang, C. Xing and Z. Miao, Chem. Rev., 117, 7762 (2017); https://doi.org/10.1021/acs.chemrev.7b00020.
B.K. Sharma, S.C. Ameta and V.K. Dwivedi, Int. J. Chem. Sci., 12, 1121 (2014).
S. Raghavan, P. Manogaran, B. Kalpattu Kuppuswami, G. Venkatraman and K.K. Gadepalli Narasimha, Med. Chem. Res., 24, 4157 (2015); https://doi.org/10.1007/s00044-015-1453-2.
Z. Nowakowska, Eur. J. Med. Chem., 42, 125 (2007); https://doi.org/10.1016/j.ejmech.2006.09.019.
S.L. Gaonkar and U.N. Vignesh, Res. Chem. Intermed., 43, 6043 (2017); https://doi.org/10.1007/s11164-017-2977-5.
B.P. Bandgar, S.S. Gawande, R.G. Bodade, J.V. Totre and C.N. Khobragade, Bioorg. Med. Chem., 18, 1364 (2010); https://doi.org/10.1016/j.bmc.2009.11.066.
A. Torres de Pinedo, P. Peñalver and J.C. Morales, Food Chem., 103, 55 (2007); https://doi.org/10.1016/j.foodchem.2006.07.026.
V.J. Ram, A. Saxena, S. Srivastava and S. Chandra, Bioorg. Med. Chem. Lett., 10, 2159 (2000); https://doi.org/10.1016/S0960-894X(00)00409-1.
G.A. Crosby, P.C. Wang and R.E. Wingard Jr., 4-(Dihydroxyhexoxy)-dihydrochalcone Sweeteners, US Patent 4204007A (1980).
M.D. Carmen, G. Barrio, J.R. Barrio, G. Walker, A. Novelli and N.J. Leonard, J. Am. Chem. Soc., 95, 4891 (1973); https://doi.org/10.1021/ja00796a021.
S.J. Buckman, K.J. Flanagan, J.D. Pera and L.A. Wienert, Organic Esters and Their Use as Ultraviolet Light Absorbers and as Heat Stabilizers, US Patent 3733297A (1973).
G.J. Macdonald and S.R. Nohr, Light-Stabilized Dyestuff Compositions, EP 0854896B1 (2002).
I. Karaman, H. Gezegen, M.B. Gurdere, A. Dingil and M. Ceylan, Chem. Biodivers., 7, 400 (2010); https://doi.org/10.1002/cbdv.200900027.
T.T. Tochigi, K.N. Ichikaimachi, M.H. Utsunomiya, S.M. Wakayama, G. Imokawa and N. Takaishi, Novel Chalcone Derivatives and Ultraviolet Absorbers Comprising the Same, US Patent 4584190A (1986).
V. Sharma, P. Kumar and D. Pathak, J. Heterocycl. Chem., 47, 491 (2010); https://doi.org/10.1002/jhet.349.
N.K. Kaushik, N. Kaushik, P. Attri, N. Kumar, C.H. Kim, A.K. Verma and E.H. Choi, Molecules, 18, 6620 (2013); https://doi.org/10.3390/molecules18066620.
S. Bonjar, S. Aghighi and N.A. Karimi, J. Biol. Sci., 4, 405 (2005).
C. Perez, M. Paul and P. Bazerque, Acta. Biol. Med. Exp, 15, 113 (1990).