Synthesis, Spectral Correlations and Biological Activities of Some (E)-[4-(Substituted Benzylidene Amino)Phenyl] (Phenyl) Methanones

Mayavel, P.; Thirumurthy, K.; Dineshkumar, S.; Thirunarayanan, Ganesamoorthy

doi:10.18052/www.scipress.com/ILCPA.39.145

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Synthesis, Spectral Correlations and Biological Activities of Some (E)-[4-(Substituted Benzylidene Amino)Phenyl] (Phenyl) Methanones

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Abstract:

A series of Schiff’s bases have been synthesized by fly-ash:p-toluenesulfonic acid (fly-ash:PTS) catalyzed microwave assisted oxidative coupling of arylamines and substituted benzaldehydes under solvent-free condition. The synthesized Schiff’s bases are characterized by their physical constants, analytical and spectroscopic data. The group frequencies of imines such as IR (v, cm^–1) and NMR (δ, ppm) spectral data was correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. The antimicrobial activities of these Schiff’s bases have been studied using Bauer-Kirby method.

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Periodical:

International Letters of Chemistry, Physics and Astronomy (Volume 39)

Pages:

145-159

DOI:

https://doi.org/10.18052/www.scipress.com/ILCPA.39.145

Citation:

P. Mayavel et al., "Synthesis, Spectral Correlations and Biological Activities of Some (E)-[4-(Substituted Benzylidene Amino)Phenyl] (Phenyl) Methanones", International Letters of Chemistry, Physics and Astronomy, Vol. 39, pp. 145-159, 2014

Online since:

October 2014

Authors:

P. Mayavel, K. Thirumurthy, S. Dineshkumar, Ganesamoorthy Thirunarayanan

Keywords:

Fly-Ash, Hammett Correlation, IR Spectra, NMR Spectra, PTS, Schiff’s Bases

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Open Access

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Creative Commons Attribution 4.0 International License

References:

[1] H. Schiff, Justus Liebigs Ann. Chem. 131 (1864) 118-119.

[2] R. Capdeville, E. Buchdunger, J. Zimmermann and A. Matter, Nat. Rev. Drug. Discov. 1 (2002) 493-502.

[3] A. Bongini, M. Panunzio, G. Piersanti, E. Bandini, G. Martelli, G. Spunta and A. Venturini, Eur. J. Org. Chem. 13 (2000) 2379-2390.

DOI: https://doi.org/10.1002/1099-0690(200007)2000:13<2379::aid-ejoc2379>3.0.co;2-f

[4] V. V. Mulwad and J. M. Shirodkar, Indian J. Heterocyclic Chem. 11 (2002) 199-202.

[5] G. Weber and J. Messerschmidt, Anal. Chim. Acta 545 (2005) 166-172.

[6] T. Fukumura, Kokai Tokkyo Koho (2008) 10pp.

[7] R. Singh and N. K. Kaushik, Main Group Met. Chem. 30 (2007) 333–344.

[8] S. Zhu, Z. Zhou and B. Zhao, Huaxue Yu Shengwu Gongcheng 25 (2008) 34-35.

[9] C. F. Zhu, G. Z. Yuan, E. H. Sheng and Y. Cui, Jiegou Huaxue 28 (2009) 1304-1310.

[10] J. Wang, Y. Song and X. Gao, Hecheng Huaxue 16 (2008) 225-226.

[11] Q. F. Cheng, X. Y. Xu, Q. F. Wang, B. H. Qian, W. J. Liu and X. J. Yang, Jie. Hua. 28 (2009) 1281-1285.

[12] S. France, M. H. Shah, A. Weatherwax, H. Wack, J. P. Roth and T. Lectka, J. Am. Chem. Soc. 127 (2005) 1206-1215.

[13] L. Blackburn and R. J. K. Taylor, Org. Lett. 3 (2001) 637-1639.

[14] M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan and J. Thanusu, Res. Chem. Intermed. 33 (2007) 541-548.

DOI: https://doi.org/10.1163/156856707782565822

[15] a) R. J. McBurney, P. C. Fernando and J. C. Walton, Res. Adv. 2 (2012) 1264-1274; b) G. Nagendrappa, Resonance 7 (2002) 59-68.

[16] A. Hasaninejad, A. Zare, H. Sharghi and M. Shekouhy, Arkivoc xi (2008) 64-74.

[17] a) C. M. Bode, A. Ting and S. E. Schaus, Tetrahedron 62 (2006) 11499-11505; b) P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron 57 (2001) 9225-9283.

DOI: https://doi.org/10.1016/s0040-4020(01)00906-1

[18] M. A. Vazquez, M. Landa, L. Reyes, M. J. Tamariz and D. Francisco, Synth. Commun. 34 (2004) 2705-2718.

[19] R. Suresh, D. Kamalakannan, K. Ranganathan, R. Arulkumaran, R. Sundararajan, S. P. Sakthinathan, S. Vijayakumar, K. Sathiyamoorthi, V. Mala, G. Vanangamudi, K. Thirumurthy, P. Mayavel and G. Thirunarayanan, Spectrochim. Acta A 101 (2013) 239-248.

DOI: https://doi.org/10.1016/j.saa.2012.09.039

[20] S. K. Srivastava, S. Srivastava and S. D. Srivastava, Indian J. Chem. 41B (2002) 2357–2363.

[21] R. S. Pattan, V. V. Krishna Reddy, F. V. Manvi and B. G. Desai, Indian J. Chem. 45B (2006) 1778-1781.

[22] a) K. Singh, M. S. Barwa and P. Tyagi, Eur. J. Med. Chem. 41 (2006) 147-153; b) S.K. Sridhar, M. Saravanana and A. Ramesh, Eur. J. Med. Chem. 36 (2001) 615-625.

[23] K. M. Mistry and K. R. Desai, Indian J. Chem. 45B (2006) 1762-1766.

[24] a) W. He, M. R. Meyers, B. Hanney, A. Spada, G. Blider, H. Galzeinski, D. Amin, S. Needle, K. Page, Z. Jayyosi and H. Perrone, Bioorg. Med. Chem. Lett. 13 (2003) 3097-3100; b) K. M. Mistry and K. S. Desai, E-J. Chem. 1 (2004) 189-193.

[25] R. Mino, L. Shuoliong, Y. Rudong and V. L. Y. Welbing, Indian J. Chem. 42 (2003) 318-321.

[26] S. T. Hazeldine, L. Polin, J. Kushner, J. Paluck, K. White, M. Edelstein, E. Palomino, T. H. Corbett and J. P. Horwitz, J. Med. Chem. 44 (2001) 1758-1776.

DOI: https://doi.org/10.1021/jm0005149

[27] A. Venturini and R. J. Gonzalez, J. Org. Chem. 67 (2002) 9089-9092.

[28] A. E. Taggi, A. M. Hafez, H. Wack, B. Young, D. Ferraris and T. Lectka, J. Am. Chem. Soc. 124 (2002) 6626-6635.

[29] C. M. L. Delpiccolo and E. G. Mata, Tetrahedron: Asymmetry 13 (2002) 905-910.

[30] K. Sathiyamoorthy, V. Mala, S. P. Sakthinathan, D. Kamalakannan, R. Suresh, G. Vanangamudi and G. Thirunarayanan, Spectrochim. Acta A 112 (2013) 245-256.

[31] G. Thirunarayanan and K. G. Sekar, International Letters of Chemistry, Physics and Astronomy 6 (2014) 39-47.

[32] R. Arulkumaran, R. Sundararajan, V. Manikandan, V. Sathiyendiran, S. Pazhamalai and G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 19 (2014) 25-15.

[33] K. G. Sekar and G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 8 (2013) 160-174.

[34] G. Thirunarayanan, Int. J. Sci. Res. Know. 1 (2013) 480-596.

[35] G. Thirunarayanan and G. Vanangamudi, Spectrochim Acta A 81 (2011) 390-396.

[36] K. G. Sekar and G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 8 (2013) 249-258.

[37] G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 9 (2013) 152-161.

[38] G. Thirunarayanan and M. Suresh, International Letters of Chemistry, Physics and Astronomy 4 (2014) 1-11.

[39] G. Thirunarayanan, Bull. Chem. Soc. Ethiop. 28 (2014) 73-79.

[40] G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 5 (2014) 89-98.

[41] G. Thirunarayanan and K. G. Sekar, J. Taibah Univ. Sci. 8 (2014) 124-136.

[42] G. Thirunarayanan, K. G. Sekar and R. Lakshmi Narayanan, International Letters of Chemistry, Physics and Astronomy 13 (2014) 88-94.

[43] P. Mayavel, K. Thirumurthy, S. Dineshkumar and G. Thirunarayanan, Q-Science Connect. (2014). doi: http: /dx. doi. org/10. 5339/connect. 2014. 10.

[44] V. Sathiyendiran, K. G. Sekar, G. Thirunarayanan, R. Arulkumaran, R. Sundararajan, D. Kamalakkannan, R. Suresh, V. Manikanadan, R. Vijayakumar and G. Vanangamudi, International Letters of Chemistry, Physics and Astronomy 11 (2014) 33-43.

DOI: https://doi.org/10.18052/www.scipress.com/ilcpa.30.33

[45] G. Thirunarayanan and G. Vanangamudi, Spectrochim. Acta A 81 (2011) 390-396.

[46] G. Thirunarayanan, M. Gopalakrishnan and G. Vanangamudi, Spectrochim. Acta A 67 (2007) 1106-1112.

[47] G. Thirunarayanan, Int. J. Chem. 1 (2012) 535-541.

[48] G. Thirunarayanan, P. Mayavel, K. Thirumurthy, G. Vanangamudi, K. Lakshmanan and K. Sekar, Int. J. Chem. 1 (2012) 166-172.

[49] G. Thirunarayanan, P. Mayavel, K. Thirumurthy, G. Vanangamudi, K. Lakshmanan and K. Sekar, J. Chil. Chem. Soc. 58 (2013) 2231-2234.

DOI: https://doi.org/10.4067/s0717-97072013000400071

[50] G. Thirunarayanan, Bull. Chem. Soc. Ethiop. 28 (2014) 73-79.

[51] S. P. Sakthinathan, R. Suresh, V. Mala, K. Sathiyamoorthi, D. Kamalakannan, K. Ranganathan, R. Arulkumaran, S. Vijayakumar, R. Sundararajan, G. Vanangamudi and G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 6 (2013).

DOI: https://doi.org/10.18052/www.scipress.com/ilcpa.11.77

[52] S. P. Sakthinathan, R. Suresh, V. Mala, K. Sathiyamoorthi, D. Kamalakannan, K. Ranganathan, S. John Joseph, G. Vanangamudi and G. Thirunarayanan, Int. J. Sci. Res. Know. 1 (2013) 472-483.

[53] B. W. Bauer, W. M. M. Kirby, J. C. Sherris and M. Truck, Am. J. Clin. Pathol. 45 (1996) 493-496.

[54] C. G. Swain and E. C. Lupton Jr, J. Am. Chem. Soc. 90 (1968) 4328-4337. ( Received 20 September 2014; accepted 28 September 2014 ).

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