Synthesis, study of structure activity relationship and evaluation of biological activities of substituted (E)-2-Benzylidene-N-Methylhyrazinecarbothioamides

Authors

  • Ganesamoorthy Thirunarayanan Government Arts College
  • R. Senbagam Government Arts College
  • M. Rajarajan Government Arts College
  • V. Manikandan Government Arts College
  • S. Balaji Government Arts College
  • G. Vanangamudi Government Arts College
  • G. Thirunarayanan Annamalai University

DOI:

https://doi.org/10.11113/mjfas.v12n4.442

Abstract

A series of ten substituted (E)-2-benzylidene-N-methylhydrazinecarbothioamides were synthesized from 4-methyl-3-thiosemicarbazide with substituted benzaldehydes. All the synthesized compounds were in good agreement with elemental and spectral data (UV, FT-IR, 1H NMR and 13C NMR). The assigned UV λmax (nm), IR νC=N (cm-1), NMR δ1H (ppm) CH=N and δ13C (ppm) C=N spectral data of (E)-2-benzylidene-N-methylhydrazinecarbothioamides correlated with Hammett constants using single and multi-regression analysis. From the results of correlation analysis substituent effects on the spectral data have been discussed. The antibacterial activity of (E)-2-benzylidene-N-methylhydrazinecarbothioamides have been studied with three Gram-positive pathogenic bacterial strains namely (B. subtilis, S. aureus and S. pyogens) and two Gram-negative strains (E. coli and P. aeruginosa). The antifungal activity of (E)-2-benzylidene-N-methyl hydrazones studied with three fungal species (A. flavus, A. niger, T. viride) using disk diffusion method.

 

Author Biographies

Ganesamoorthy Thirunarayanan, Government Arts College

PG & Research Department of Chemistry,

R. Senbagam, Government Arts College

PG & Research Department of Chemistry,

M. Rajarajan, Government Arts College

PG & Research Department of Chemistry,

V. Manikandan, Government Arts College

PG & Research Department of Chemistry

S. Balaji, Government Arts College

PG & Research Department of Chemistry

G. Vanangamudi, Government Arts College

PG & Research Department of Chemistry

G. Thirunarayanan, Annamalai University

Department of Chemistry

References

(1) N.P. Belskaya, W. Dehaen and V.A. Bakulev, 2010. Arkivoc.(i):275-332

(2) S. Kim, J.-Y, 2004.Yoon. Sci. Synth. (27): 671-772.

(3) R. Brehme, D. Enders, R. Fernandez and J.M. Lassaletta, 2007. Eur. J. Org. Chem, (34): 5629-5660.

(4) J.P. Corhnelissen, J.H. Van Diemen, L.R. Groeneveld, J.G. Haasnoot, A.L. Spek and J. Reedisk, 1992.Inorg. Chem, (31): 198-202.

(5) S.N. Dubey and B. Kaushik,Indian J. Chem, 1985. (24A): 950 -953.

(6) H.C. Brown and Y. Okamoto, J. Am. Chem. Soc. 1957. (79): 1913.

(7) G. Thirunarayanan, M. Gopalakrishnan and G.Vanangamudi, 2007. Spectrochim. Acta., 67(A): 1106 -1112

(8) M.S. Flett, 1948.Trans Faraday Soc, (44): 767-774.

(9) G. Thirunarayanan and G. Vanangamudi, 2011.Indian J. Chem, 50B(4): 593-604

(10) D.R. Richardson and P.V. Bernhardt, 1999. J. Biol. Inorg. Chem, (4): 266-273.

(11) G.Thirunarayanan, V.Sathiyendiran, G.Vanangamudi, R.Arulkumaran, V. Manikandan, R. Suresh, D. Kamalakkannan, S. P. Sakthinathan, R. Sundararajan, K. Sathiyamorthi, S. Balaji, R. Vijayakumar and R. Senbagam, 2015. Int. Lett. Chem. Phys. Astro, (50): 9-16.

(12) S. Balaji, M. Rajarajan, R. Vijayakumar, V. Manikandan, R. Senbagam , G. Vanangamudi and G. Thirunarayanan, 2015. Int. Lett. Chem. Phys. Astro, (57): 145-155.

(13) M. Rajarajan, R. Senbagam, R. Vijayakumar, V. Manikandan, S. Balaji, G. Vanangamudi and G. Thirunarayanan, 2015. World. Sci. News (3): 155-171.

(14) L. Ramamohan, R.K. Shikkaragol, S.D. Angadi and V.H. Kulkarni, 1995. Asian. J. Pure Appl.Chem., 1(2): 86

(15) P. Melnyk, V. Leroux, C. Sergheraert and P. Grellier, 2006. Bioorg. Med. Chem. Lett, (16): 31 -35.

(16) L.F.C.C. Leite, M.N. Ramos, J.B.P. da Silva, A.L.P. Miranda, C.A.M. Fraga and E.J. Barreiro, 1999. Farmaco, (54): 747-757.

(17) P.C. Lima, L.M. Lima, K.C.M. da Silva, P.H.O. Leda, A.L.P. de Miranda, C.A.M. Fraga and E.J. Barreiro, 2000. Eur J Med Chem, (35): 187-203.

(18) A.C. Cunha, J.M. Figueiredo, J.L.M. Tributino, A.L.P. Miranda, H.C. Castro, R.B. Zingali, C.A.M. Fraga, M.C.B.V. de Souza, V.F. Ferreira and E.J. Barreiro, 2003. Bio.org. Med Chem, (11): 2051-2059.

(19) K.K. Bedia, O. Elcin, U. Seda, K. Fatma, S. Nathaly, R. Sevim and A. Dimoglo, 2006. Eur. J. Med. Chem, (41): 1253-1261.

(20) N. Terzioglu and A. Gursoy, 2003. Eur. J. Med. Chem, (38): 781-786.

(21) W. W. Wardakhan, E.-S. Nahed Nasser Eid, and R. M. Mohareb, 2013. Acta Pharmaceutica, (63)1: 45-57.

(22) S. Suzen, B. Tekiner-Gulbas, H. Shirinzadeh, D. Uslu, H. Gurer-Orhan, M. Gumustas and S.A. Ozkan, 2013. J. Enzym. Inhib. Med. Chem, (28): 1143-1155.

(23) G. Turan-Zitouni, M.D. Altintop, A. Ozdemir, F. Demirci, U. Abu Mohsen and Z.A. Kaplancikli, 2013. J. Enzym. Inhib. Med Chem, (28): 1211-1216.

(24) N. Tabanca, D.E. Wedge, A. Ali, I.A. Khan, Z.A. Kaplancikli and M.D. Altintop, (2013).Med. Chem. Res, (22): 2602-2609.

(25) G. Thirunarayanan and G. Vanangamudi , Spectrochim.Acta, 2011. (81): 390-396.

(26) P. Romulo Tenorio, Cristiane S. Carvalho, Carla S. Pessanha, Jose´ G. De Lima, Antonio R. De Faria, Antonio J. Alves, Edesio J. T. De Melob and Alexandre J. S. Goesa, 2005. Bioorg. Med. Chem. Lett, (15): 2575-2578.

(27) G. Thirunarayanan, G. Vanangamudi and M. Subramanian, 2013.Org. Chem. Indian. J, 9(1): 1-16.

(28) M.Rajarajan, R.Vijayakumar, R.senbagam, S.balaji, V.Manaikandan, G.Vanangamudi and G.Thirunarayan, 2015.Indian J. Chem, (55B): 197-206

(29) R. Senbagam , R. Vijayakumar , M. Rajarajan , S. Balaji , V. Manikandan ,G. Vanangamudi and G. Thirunarayanan, 2016. Karbala. Int. J. Mod. Sci, (20): 1-7.

(30) R. Vijayakumar, M. Rajarajan, S. Balaji1, V. Manikandan, R. Senbagam, G. Vanangamudi, G. Thirunarayanan, 2015. World. Sci. News, (3): 81-98.

(31) R.Senbagam, M.Rajarajan, R.Vijayakumar, V. Manikandan, S. Balaji, G. Vanangamudi and G. Thirunarayan, 2015. Int. Lett. Chem. Phys. Astro, (53):154-164.

(32) C. G. Swain and E. C. Lupton, 1968. J. Am. Chem. Soc, (90): 4328-4337

(33) A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M.Truck, Am. J. Clin. Pathol, 1966. (45): 493-496.

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Published

12-02-2017