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GREEN SYNTHESIS OF NEW AMINO ACID SCHIFF BASES AND THEIR BIOLOGICAL ACTIVITIES

Year 2016, Volume: 3 Issue: 3, 15 - 24, 08.01.2017
https://doi.org/10.18596/jotcsa.14900

Abstract

In this study, four new and two known amino acid Schiff base compounds derived from the condensation reaction of benzaldehyde, salicylaldehyde, pyrrole-2-carbaldehyde, pyridine-2-carbaldehyde, fluorene-2-carbaldehyde and terephthalaldehyde with 2-phenylglycine methyl ester hydrochloride have been synthesized by both conventional method and microwave irradiation protocol. The new compounds were characterized by FTIR, 1H-NMR, LC-MS and electronic spectral studies. A comparative study between conventional heating and microwave irradiation has also been reported. Based on these results, with the microwave synthesis, the yield of the products was increased from 37% upto 96% as compared to conventional method. By microwave, reactions were completed within 5.5-8.5 minutes and the products were obtained in good to high yields, with reduced time, waste, and formation byproduct. DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging effect were performed to determine antioxidant activities of the new compounds. All of the compounds exhibited significant activities in DPPH radical scavenging. 

References

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  • Bashiardes G, Cano C, Mauze B. Regio- and enantioselective synthesis of novel functionalized pyranopyrrolidines by, 1,3- dipolar cycloaddition of carbohydrates. Synlett. 2005; 4: 587-590. DOI: 10.1002/chin.200532134.
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  • Marquez V, A, Rodriguez C, H, Morales V, E, Quintanar S, C, Chuaqui J, C, A. Synthesis and stereochemistry of bicyclic pyrrolidines obtained by 1,3- dipolar cycloaddition between α-amino acid ester aldimines and maleimides. Boletin de la Sociedad Chilena de Quimica. 1991;36(1):43-55. http://hdl.handle.net/10533/54505.
  • Sharma P, K, and Dubey S,N. Synthesis and structural studies of iron(II) complexes with N-salicylidene and N-(2-hydroxy-1-naphthylidene) amino acids. Indian Journal of Chemistry, 33A. 1994; 1113-1115. https://www.scopus.com/search/form.
  • Wei Q, Y, Xiong J, J, Jiang H, Zhang C, Wen Y. The antimicrobial activities of the cinnamaldehyde adducts with amino acids. International Journal of Food Microbiology. 2011; 150(2-3): 164. http://www.ncbi.nlm.nih.gov/pubmed/21856030.
  • Ando R, Inden H, Sugino M, Ono H, Sakaeda D, Yagyu T, Maeda M. Spectroscopic characterization of amino acid and amino acid ester-Schiff-base complexes of oxovanadium and their catalysis in sulfide oxidation. Inorganica Chimica Acta. 2004; 357(5): 1337- 1344. DOI:10.1016/j.ica.2003.10.030.
  • Mishra A, P, Tiwari A, Jain R, K. Microwave induced synthesis and characterization of semiconducting 2-Thiophenecarboxaldehyde metal complexes. Advanced Meterial Letters. 2012; 3: 213-219. DOI: 10.5185/amlett.2011.9307.
  • Sharma K, Singh R, Fahmi N, Singh R, V. Microwave assisted synthesis, characterization and biological evalution of palladium and platinum complexes with azamethines. Spectrochimica Acta. 2010; 75A: 422-427. DOI:10.1016/j.saa.2009.10.052.
  • Peksel A, Altas-Kiymaz N, Imamaoglu S. Evaluation of antioxidant and antifungal potential of Asphodelus aestivus Brot. growing in Turkey. Journal of Medicinal Plants Research. 2012 Jan; 6(2): 253-265. DOI: 10.5897/JMPR11.1229.
  • Amarowicz R, Estrella I, Hernandez T, Robredo S, Troszynska A, Kosinska A, Pegg R, B. Free radical-scavenging capacity, antioxidant activity and phenolic composition of green lnetil (Lens culinaris). Food Chemistry. 2010; 121: 705-711.
  • DOİ:10.1016/j.foodchem.2010.01.009.
Year 2016, Volume: 3 Issue: 3, 15 - 24, 08.01.2017
https://doi.org/10.18596/jotcsa.14900

Abstract

References

  • Panda J, Patro V, J, Sahoo B, M, Mishra J. Microwave mediated organic reaction: a convenient approach for rapid and efficient synthesis of biologically active substituted 1,3-dihydro-2h-indol-2-one derivatives. Journal of Nanoparticles, 2013; 549502: 1-5. http://dx.doi.org/10.1155/2013/272598.
  • Abirami M, Nadaraj V. Synthesis of schiff base under solvent-free condition: as a green approach. International Journal of ChemTech Research. 2014; 6(4): 2534-2538. http://sphinxsai.com/2014/vol6pt4/5/(2534-2538)Jul-Aug14.
  • Naglah A, M, Awad H, M, Bhat M, A, Al-Omar M, A. Amr A, G, E. Microwave assisted synthesis and antimicrobial activity of some novel isatin schiff bases linked to nicotinic acid via certain amino acid bridge. Journal of Chemistry. 2015; 364841: 1-8. DOI: 10.1155/2015/364841.
  • Alavi H, Taheri M, Daryani M. Enantioselective synthesis of chiral alfa amino acids by phase transfer catalysts. Oriental Journal of Chemistry. 2013; 29(1): 135-143. http://orientjchem.org/dnload.
  • Kaid R, S, Djafri A, Djafri F. The use of bentonite in heterogeneous medium as an efficient recyclable catalyst in the synthesis of iminoesters. Mediterranean Journal of Chemistry. 2011; 1: 1-7. DOI: 10.13171/mjc.1.1.2011.20.04.20.
  • Bashiardes G, Cano C, Mauze B. Regio- and enantioselective synthesis of novel functionalized pyranopyrrolidines by, 1,3- dipolar cycloaddition of carbohydrates. Synlett. 2005; 4: 587-590. DOI: 10.1002/chin.200532134.
  • Padwa A, Verlag T, G. Carbons with two carbon- heteroatom bonds: heteroatom analogues of aldehydes and ketones. Science of Synthesis; 2004. 1174 p. ISBN: 3-13-118781-6.
  • Zheng Y, S, Jiang A. Asymmetric synthesis of 2,4-dihydroxymethylpyrrolidine derivatives and their inducing ability for epoxidation of olefins. Chinese Journal of Organic Chemistry 2003; 23(10): 1114-1119. http://siocjournal.cn/Jwk_yjhx/EN/Y2003/V23/I10/1114.
  • Marquez V, A, Rodriguez C, H, Morales V, E, Quintanar S, C, Chuaqui J, C, A. Synthesis and stereochemistry of bicyclic pyrrolidines obtained by 1,3- dipolar cycloaddition between α-amino acid ester aldimines and maleimides. Boletin de la Sociedad Chilena de Quimica. 1991;36(1):43-55. http://hdl.handle.net/10533/54505.
  • Sharma P, K, and Dubey S,N. Synthesis and structural studies of iron(II) complexes with N-salicylidene and N-(2-hydroxy-1-naphthylidene) amino acids. Indian Journal of Chemistry, 33A. 1994; 1113-1115. https://www.scopus.com/search/form.
  • Wei Q, Y, Xiong J, J, Jiang H, Zhang C, Wen Y. The antimicrobial activities of the cinnamaldehyde adducts with amino acids. International Journal of Food Microbiology. 2011; 150(2-3): 164. http://www.ncbi.nlm.nih.gov/pubmed/21856030.
  • Ando R, Inden H, Sugino M, Ono H, Sakaeda D, Yagyu T, Maeda M. Spectroscopic characterization of amino acid and amino acid ester-Schiff-base complexes of oxovanadium and their catalysis in sulfide oxidation. Inorganica Chimica Acta. 2004; 357(5): 1337- 1344. DOI:10.1016/j.ica.2003.10.030.
  • Mishra A, P, Tiwari A, Jain R, K. Microwave induced synthesis and characterization of semiconducting 2-Thiophenecarboxaldehyde metal complexes. Advanced Meterial Letters. 2012; 3: 213-219. DOI: 10.5185/amlett.2011.9307.
  • Sharma K, Singh R, Fahmi N, Singh R, V. Microwave assisted synthesis, characterization and biological evalution of palladium and platinum complexes with azamethines. Spectrochimica Acta. 2010; 75A: 422-427. DOI:10.1016/j.saa.2009.10.052.
  • Peksel A, Altas-Kiymaz N, Imamaoglu S. Evaluation of antioxidant and antifungal potential of Asphodelus aestivus Brot. growing in Turkey. Journal of Medicinal Plants Research. 2012 Jan; 6(2): 253-265. DOI: 10.5897/JMPR11.1229.
  • Amarowicz R, Estrella I, Hernandez T, Robredo S, Troszynska A, Kosinska A, Pegg R, B. Free radical-scavenging capacity, antioxidant activity and phenolic composition of green lnetil (Lens culinaris). Food Chemistry. 2010; 121: 705-711.
  • DOİ:10.1016/j.foodchem.2010.01.009.
There are 17 citations in total.

Details

Journal Section Articles
Authors

Cigdem Yorur-goreci This is me

Zulal Demir This is me

Nilay Altaş This is me

Publication Date January 8, 2017
Submission Date July 1, 2016
Published in Issue Year 2016 Volume: 3 Issue: 3

Cite

Vancouver Yorur-goreci C, Demir Z, Altaş N. GREEN SYNTHESIS OF NEW AMINO ACID SCHIFF BASES AND THEIR BIOLOGICAL ACTIVITIES. JOTCSA. 2017;3(3):15-24.