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Synthesis, Characterization and Biological Study of Some (E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-ones

Received: 9 December 2016    Accepted: 4 January 2017    Published: 24 January 2017
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Abstract

About eleven substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones have been synthesized by Crossed-Aldol condensation using simple stirring of 5-bromo-2-thiophen aldehyde and various substituted acetophenones at room temperature. The obtained yields of this condensation was more than 89%. They are characterized by their analytical, UV, FT-IR and NMR spectral data. The antimicrobial activities of all synthesized chalcones have been evaluated by Bauer-Kirby disc diffusion method using gram positive and gram negative bacterial and fungal strains. From the mm of zone of inhibition values the anti-bacterial and antifungal activities of all ketones have been discussed.

Published in International Journal of Bioorganic Chemistry (Volume 1, Issue 1)
DOI 10.11648/j.ijbc.20160101.13
Page(s) 21-30
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This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

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Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

(E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-Ones, IR Spectra, NMR Spectra, Antibacterial and Antifungal Activities

References
[1] Trost, B. M.; The atom economy--a search for synthetic efficiency. Science., 1991, 254, 1471-1478.
[2] Thirunarayanan, G.; Vanangamudi, G.; Synthesis of some aryl chalcones using silica sulphuric acid reagent under solvent free conditions. E. J. Chem. 2007, 4 (1), 90-97.
[3] Ranganathan, K.; Arulkumaran, R.; Kamalakkannan, D.; Sundararajan, R.; Sakthinathan, S. P.; Vijayakumar, S.; Suresh, R.; Vanangamudi, G.; Thirumurthy, K.; Mayavel, P.; Thirunrayanan, G.; Silica-H2SO4 catalyzed environmentally benign crossed aldol condensation: synthesis, spectral studies and biological activities of some 5-chloro-2-thienyl chalcones. Int. J. Pharm. Med. and Bio. Sci. 2012, 1 (1), 62-85.
[4] Venkat Reddy, G.; Maitraie, G.; Narsaiah, D.; Rambahu, B.; Rao, R.; Microwave assisted Knoevenagel condensation: A facile method for the synthesis of chalcones. Synth. Commun. 2001, 31 (18), 2881-2884.
[5] John Joseph, S.; Arulkumaran, R.; Kamalakkannan, D.; Sakthinathan, S. P.; Sundararajan, R.; Suresh, R.; Vijayakumar, S.; Ranganathan, K.; Kalyanasundaram, N.; Vanangamudi, G.; Thirunarayanan, G.; Spectral correlation analysis and antimicrobial activities of some 2,4-dimethoxy phenyl chalcones. Int. Lett. Chem. and Phy. Astro. 2014, 4, 48-65.
[6] Orsini, F.; Sello, G.; Fumagalli, T.; One-Pot Wittig Reactions in Water and in the Presence of a Surfactant. Synlett. 2006, 11, 1717-1718.
[7] Thirunarayanan, G.; Vanangamudi, G.; Synthesis of some 4-bromo-1-naphthyl chalcones using silica-sulfuric acid reagent under solvent free conditions. Arkivoc. 2006, 12, 58-64.
[8] Thirunarayanan, G.; Insect antifeedant potent chalcones. J. Ind. Chem. Soc. 2008, 84, 447-451.
[9] Basaif, S. A.; Sobahi, T. R.; Khalil, A. K.; Hassan, M. A.; Stereoselective crossed-aldol condensation of hetarylmethyl ketones with aromatic aldehydes in water: Synthesis of (2E)-3-aryl-1-hetarylprop-2-en-1-ones. Bulletin of the Korean Chem. Soc. 2005, 26 (11), 1677-1681.
[10] Xu, Q.; Yang, Z.; Yin, D.; Zhang, F.; Synthesis of chalcones catalyzed by a novel solid sulfonic acid from bamboo. Catal. Commun. 2008, 9(1), 1579-1582.
[11] Zhang, Z.; Dong, Y. W.; Wang, G. W.; Efficient and clean aldol condensation catalyzed by sodium carbonate in water. Chem. Lett. 2003, 32(10), 966-967.
[12] Thirunarayanan, G.; Fly-ash catalyzed Friedel-Crafts cinnamoylation reaction in solvent free conditions: synthesis of α, β-unsaturated ketones under microwave irradiation. IUP. J. Chem. 2010, 3 (4), 35-54.
[13] Thirunarayanan, G.; Thirumurthy, K.; Vanangamudi, G.; Subramanian, M.; Arulkumaran, R.; Kamalakkannan, D.; Sundararajan, R.; Sakthinathan, S. P.; Vijayakumar, S.; Ranganathan, K.; Suresh, R.; Fly-ash: water catalyzed greener synthesis and insect antifeedant activities of some chalcones. Elixir Org. Chem. 2012, 45, 7898-7905.
[14] Thirunarayanan, G.; Mayavel, P.; Thirumurthy, K.; Fly-ash: H2SO4 catalyzed solvent free efficient synthesis of some aryl chalcones under microwave irradiation. Spectrochimica Acta. 2012, 91A, 18-22.
[15] Sundararajan, R.; Arulkumaran, R.; Vijayakumar, S.; Kamalakkannan, D.; Suresh, R.; Ranganathan, K.; Sakthinathan, S. P.; Vanangamudi, G.; Thirumurthy, K.; Mayavel, P.; Thirunarayanan, G.; Solid fly-ash: PTS catalyzed green aldol condensation: Synthesis, spectral correlation, antimicrobial and insect antifeedant potent of some aryl chalcones. Int. J. Pharm. Chem. Sci. 2012, 1 (4), 1657-1677.
[16] Thirunarayanan, G.; Surya, S.; Srinivasan, S.; Vanangamudi, G.; Sathiyendiran, V.; Synthesis and insect antifeedant activities of some substituted styryl 3,4-dichlorophenyl ketones. Spectrochim. Acta. 2010, 75A, 152-156.
[17] Janaki, P.; Sekar, K. G.; Thirunarayanan, G.; SiO2-H3PO4 catalyzed solvent free Aldol condensation: Synthesis and spectral correlations of some antimicrobial potent aryl (E) 2-propen-1-ones. Org. Chem: An Indian J. 2013, 9 (2), 68-80.
[18] Arulkumaran, R.; Vijayakumar, S.; Sundararajan, R.; Sakthinathan, S. P.; Kamalakkannan, D.; Suresh, R.; Ranganathan, K.; Vanangamudi, G.; Thirunarayanan, G.; Thionylchloride catalyzed Aldol condensation: Synthesis, spectral correlation and antibacterial activities of some 3, 5-dichloro-2-hydroxy phenyl chalcones. Int. Lett. Chem. Phys. Astro. 2012, 4, 17-38.
[19] Kamalakkannan, D.; Vanangamudi, G.; Arulkumaran, R.; Thirumurthy, K.; Mayavel, P.; Thirunarayanan, G.; Synthesis, spectral, electrochemical and antimicrobial studies of some 2-pyrrolyl chalcones. Elixir Org. Chem. 2012, 46, 8157-8166.
[20] Fouda, A. S.; Shafie, A. A. E.; Gadow, H. S.; The use of chalcones as corrosion inhibitors for nickel corrosion: in nitric acid solution. Portugaliae Electrochim Acta. 2002, 20, 13-23.
[21] Sekar, K. G.; Thirunarayanan, G.; Solvent-free synthesis and spectral studies of some 9-anthryl-1H-pyrazolines. Int. J. Sci. Res. Know. 2013, 1, 299-307.
[22] Thirunarayanan, G.; Synthesis, Characterization and biological activities of some flavones derivatives. Asi. J. Chem. 2003, 15, 907-910.
[23] Carlo, G. D.; Masolo, N.; Izzo, A. A.; Capasso, F.; Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci. 1999, 65(4), 337-353.
[24] Ko, H. H.; Tsao, L. T.; Yu, K. L.; Liu, C. T.; Wang, J. P.; Lin, C. N.; Structure-activity relationship studies on chalcone derivatives. the potent inhibition of chemical mediators release. Bioorg. and Med. Chem. 2003, 11 (1), 105-111.
[25] Matsuda, H.; Morikawa, T.; Ando, S.; Iwao, T.; Masayuki, Y.; Structural Requirements of Flavonoids for Nitric Oxide Production Inhibitory Activity and Mechanism of Action. Bioorg. and Med. Chem. 2003, 11, 1995-2000.
[26] Herencia, F.; Ferrandiz, M. L.; Ubeda, A.; Dominguez, J. N.; Charris, J. E; Lobo, G. M.; Alcaraz, M.; Synthesis and anti-inflammatory activity of chalcone derivatives. J. Bioorg. and Med. Chem. 1998, 8, 1169-1174.
[27] Gein, V. L.; Gein, L. F.; Chirkova, M. V.; Mikhalev, V. A.; Voronina, E. V.; Synthesis, properties, and antimicrobial activity of 3-hydrazones of 1-aryl-5-methyl-1,5-ethoxycarbonylpyrrolidine-2,3-diones. Pharma. Chem. J. 2005, 39(8), 413-417.
[28] Bayrak, H.; Demirbas, A.; Demirbas, N.; Karaoglu, S. A.; Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. Eur. J. Med. Chem. 2009, 44, 4362-6.
[29] Lin, Y. M.; Hou, Y.; Flavin, M. T.; Zhou, L. M.; Nie, W.; Chen, F. C.; Chalcones and flavonoids as anti-tuberculosis agents. Bioorg. and Med. Chem. 2002, 10, 2795-2802.
[30] Liu, M.; Wilairat, P.; Go, M. L.; Antimalarial alkoxylated and hydroxylated chalcones [corrected]: structure-activity relationship analysis. J. Med. Chem. 2001, 44, 4443-4452.
[31] Lembege, M. V.; Moreau, S.; Larrouture, S.; Montaudon, C.; Robert, J.; Nuhrich, A.; Synthesis and antiproliferative activity of aryl- and heteroaryl-hydrazones derived from xanthone carbaldehydes. Eur. J. Med. Chem. 2008, 43, 1336-1343.
[32] Raval, J. P.; Patel, N. H.; Patel, H. V.; Patel, P. S.; In vitro antimycobacterial activity of novel N0-(4-(substituted phenyl amino)-6-(pyridin-2-ylamino)-1,3,5-triazin-2-yl) isonicotinohydrazide. Med. Chem. Res. 2011, 20, 274-279.
[33] Bijev, A.; New heterocyclic hydrazones in the search for antitubercular agents: Synthesis and in vitro evaluations. Lett. Drug. Des. Discov. 2006, 3, 506-512.
[34] Morissear, C.; Du, D.; Newman, T. W.; Hammock, B. D.; Mechanism of mammalian soluble epoxide hydrolase inhibition by chalcone oxide derivatives. Arch. Bio. Chem. Bio. Phy. 1998, 356 (2), 214-228.
[35] Khobragade, C. N.; Bodade, R. G.; Shinde, M. S.; Jaju, D. R.; Bhosle, R. B.; Dawane, B. S.; Enzym, J.; Microbial and xanthine dehydrogenase inhibitory activity of some flavones. Inhibit Med. Chem. 2008, 23 (3), 341-346.
[36] Nerya, O.; Musa, K.; Khatib, S.; Tamir, S.; Vaya, J.; Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers. Phytochemistr. 2004, 65 (10), 1389-1395.
[37] Miranda, C. L.; Aponso, G. L. M.; Sterens, J. F.; Deinz, M. L.; Buhler, D. R.; Antioxidant properties of ditert-butylhydroxylated flavonoids. Free Radical Bio. Med. 2000, 29 (9), 900-912.
[38] Kucukguzel, S. G.; Mazi, A.; Sahin, F.; Ozturk, S.; Stables, J.; Synthesis and biological activities of diflunisal hydrazide-hydrazones. Eur. J. Med. Chem. 2003, 38(11-12), 1005-1013.
[39] Bauer, A. W.; Kirby, W. M. M.; Sherris, J. C.; Truck, M.; Antibiotic susceptibility testing by a standardized single disk method. Am. J. Clin. Patho. 1966, 45(4), 493-496.
[40] Atlas, R. M.; Hand book of micro biological media. London, CRC Press 2004, 1226, ISBN 0-8493-1818-1.
[41] Thirunarayanan, G.; Vanangamudi, G.; Subramanian, M.; Insect antifeedant potent substituted styryl 5-methyl-2-furyl ketones. Elixir. Org. Chem., 2012, 43, 6987-6989.
[42] Aziz, R. K.; Kansal, R.; Aronow, B. J.; Taylor, W. L.; Rowe, S. L.; Kubal, M.; Chhatwal, G. S.; Walker. M. J.; Microevolution of Group A Streptococci In Vivo: Capturing Regulatory Networks Engaged in Sociomicrobiology, Niche Adaptation, and Hypervirulence. Kotb Ahmed. 2010.
[43] Smith, K. J.; Neafie, R.; Yeager, J.; Skelton, H. J.; Micrococcus folliculitis in HIV-1 disease. Brit. J. Dermatology. 1999, 141, 558-561.
[44] Kluytmans, J.; Blekum, A. V.; Verbrugh, H.; Nasal carriage of Staphylococcus aureus: epidemiology, underlying mechanisms, and associated risks. Clin. Microbiol. Rev. 1997, 10, 505-520.
[45] Perez, A. R.; Abanes-De, A.; Mello, M.; Pogliano, K.; SpoIIB localizes to active sites of septal biogenesis and spatially regulates septal thinning during engulfment in bacillus subtilis. J. Bacteriology. 2000, 182 (4), 1096-108.
[46] Wei, Y.; Havasy, T.; McPherson, D. C.; Popham, D. L.; Rod shape determination by the Bacillus subtilis class B penicillin-binding proteins encoded by pbpA and pbpH. J. Bacteriolo. 2003, 185 (16), 4717-4726.
[47] Lecointre, G.; Rachdi, L.; Darlu, P.; Denamur, E.; Escherichia coli molecular phylogeny using the incongruence length difference test. Mol. Biol. Evol.1998, 15 (12), 1685-1695.
[48] Laboratory Methods for the Diagnosis of Vibrio cholerae" (PDF). Centre for Disease Control. Retrieved 29 October 2013.
[49] Brisse, S.; Grimont, F.; AD, P.; The Genus Klebsiella. Prokaryotes. New York, NY: Springer New York. 2006, 6, 159-196.
[50] O'hara, C. M.; Brenner, F. W.; Miller, J. M.; Classification, identification, and clinical significance of Proteus, Providencia, and Morganella. Clin Microbiol Rev. 2000, 13(4), 534-546.
[51] Cornelis, P.; Expressing genes in different Escherichia coli compartments. Curr. Opin. Biotechnol. 2000, 11 (5), 450-454.
[52] Dominguesa, F. C.; Queiroza, J. A.; Cabralb, J. M. S.; Fonsecab, L. P.; The influence of culture conditions on mycelial structure and cellulase production by Trichoderma reesei Rut C-30. Enz. Microb. Tech. 2000, 26 (5-6), 394-401.
[53] Pseudomonas, B. H. I.; In: Baron’s Med. Micro. biol., Univ. of Texas Medical Branch.,(4th ed.,) 1996.
[54] Abdel-Fattah, G. M.; Shabana, Y. M.; Harzinum, A. E. T.; Trichoderma harzianum: a biocontrol agent against Bipolaris oryzae. Mycopathology. 2007, 164(2), 81-89.
[55] Samson, R. A.; Houvbraken, J.; Summerbell, R. C.; Flannigan, B.; Miller, J. D.; Common and important species of fungi and actinomycetes in indoor environment. Micro. Org. Home and Indoor Work Environ., 2001, 287-474.
[56] Oswa, S.; Jukes, T. H.; Watanabe, K.; Muto, A.; Recent evidence for evolution of the genetic code. Micro. Biol. Rev., 1992, 56 (1), 229-264.
[57] Ebbehog, N. E.; Hansen, M. O.; Sigsgaard, T.; Larsen, L.; Building-related symptoms and molds: a two-step intervention study. Indoor Air. 2002, 12, 273-277.
[58] Madigan, M.; Martinko Brock, J.; Biol. of Micro. Organism. (11th Edition).
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    P. Christuraj, P. R. Rajakumar, C. Geetha, G. Vanangamudi, R. Arulkumran, et al. (2017). Synthesis, Characterization and Biological Study of Some (E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-ones. International Journal of Bioorganic Chemistry, 1(1), 21-30. https://doi.org/10.11648/j.ijbc.20160101.13

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    ACS Style

    P. Christuraj; P. R. Rajakumar; C. Geetha; G. Vanangamudi; R. Arulkumran, et al. Synthesis, Characterization and Biological Study of Some (E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-ones. Int. J. Bioorg. Chem. 2017, 1(1), 21-30. doi: 10.11648/j.ijbc.20160101.13

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    AMA Style

    P. Christuraj, P. R. Rajakumar, C. Geetha, G. Vanangamudi, R. Arulkumran, et al. Synthesis, Characterization and Biological Study of Some (E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-ones. Int J Bioorg Chem. 2017;1(1):21-30. doi: 10.11648/j.ijbc.20160101.13

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  • @article{10.11648/j.ijbc.20160101.13,
      author = {P. Christuraj and P. R. Rajakumar and C. Geetha and G. Vanangamudi and R. Arulkumran and R. Sundararajan and G. Thirunarayanan},
      title = {Synthesis, Characterization and Biological Study of Some (E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-ones},
      journal = {International Journal of Bioorganic Chemistry},
      volume = {1},
      number = {1},
      pages = {21-30},
      doi = {10.11648/j.ijbc.20160101.13},
      url = {https://doi.org/10.11648/j.ijbc.20160101.13},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijbc.20160101.13},
      abstract = {About eleven substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones have been synthesized by Crossed-Aldol condensation using simple stirring of 5-bromo-2-thiophen aldehyde and various substituted acetophenones at room temperature. The obtained yields of this condensation was more than 89%. They are characterized by their analytical, UV, FT-IR and NMR spectral data. The antimicrobial activities of all synthesized chalcones have been evaluated by Bauer-Kirby disc diffusion method using gram positive and gram negative bacterial and fungal strains. From the mm of zone of inhibition values the anti-bacterial and antifungal activities of all ketones have been discussed.},
     year = {2017}
    }
    

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  • TY  - JOUR
    T1  - Synthesis, Characterization and Biological Study of Some (E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-ones
    AU  - P. Christuraj
    AU  - P. R. Rajakumar
    AU  - C. Geetha
    AU  - G. Vanangamudi
    AU  - R. Arulkumran
    AU  - R. Sundararajan
    AU  - G. Thirunarayanan
    Y1  - 2017/01/24
    PY  - 2017
    N1  - https://doi.org/10.11648/j.ijbc.20160101.13
    DO  - 10.11648/j.ijbc.20160101.13
    T2  - International Journal of Bioorganic Chemistry
    JF  - International Journal of Bioorganic Chemistry
    JO  - International Journal of Bioorganic Chemistry
    SP  - 21
    EP  - 30
    PB  - Science Publishing Group
    SN  - 2578-9392
    UR  - https://doi.org/10.11648/j.ijbc.20160101.13
    AB  - About eleven substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones have been synthesized by Crossed-Aldol condensation using simple stirring of 5-bromo-2-thiophen aldehyde and various substituted acetophenones at room temperature. The obtained yields of this condensation was more than 89%. They are characterized by their analytical, UV, FT-IR and NMR spectral data. The antimicrobial activities of all synthesized chalcones have been evaluated by Bauer-Kirby disc diffusion method using gram positive and gram negative bacterial and fungal strains. From the mm of zone of inhibition values the anti-bacterial and antifungal activities of all ketones have been discussed.
    VL  - 1
    IS  - 1
    ER  - 

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Author Information
  • Post Graduate and Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram, India

  • Post Graduate and Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram, India

  • Post Graduate and Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram, India

  • Post Graduate and Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram, India

  • Post Graduate and Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram, India

  • Post Graduate and Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram, India

  • Chemistry Department, Annamalai University, Annamalainagar, India

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