Synthesis and Antibacterial Activity of (E)-N'-[4-{2-(4-Fluorophenylthio)ethoxy}-3-cyano-5-methoxybenzylidene]-substituted benzohydrazide Derivatives

Lokamaheshwari Dommati; B. Satyanarayana; P. Gayatri Hela; B. Ram; G. Srinivas

doi:10.14233/ajchem.2016.19776

Issue

Vol. 28 No. 7 (2016): Vol 28 Issue 7

Issue Published : March 31, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Antibacterial Activity of (E)-N'-[4-{2-(4-Fluorophenylthio)ethoxy}-3-cyano-5-methoxybenzylidene]-substituted benzohydrazide Derivatives

https://doi.org/10.14233/ajchem.2016.19776

Lokamaheshwari Dommati

Department of Chemistry, Jawaharlal Nehru Technological University, Hyderabad-500 072, India; Green Evolution Laboratories, Wangapally Village-500 085, India

B. Satyanarayana

Macleods Pharmaceuticals Ltd., Bhuvaneshwari Nagar, Andheri, Mumbai-400 059, India

P. Gayatri Hela

Siri Lifesciences, Banglore-560 066, India

B. Ram

Green Evolution Laboratories, Wangapally Village-500 085, India

G. Srinivas

Green Evolution Laboratories, Wangapally Village-500 085, India

Corresponding Author(s) : Lokamaheshwari Dommati

lokamaheshwari2015@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 7 (2016): Vol 28 Issue 7
Article Published : March 31, 2016

Abstract

Commercially available vanillin was used as the starting material for the preparation of some new (E)-N’-[4-{2-(4-fluorophenylthio)-ethoxy}-3-cyano-5-methoxybenzylidene]-4-substituted benzohydrazide derivatives (8.1 to 8.10) in quantitative yields. The structural confirmations of all the newly synthesized hydrazone derivatives were established on the basis of ¹H NMR, mass and IR data. Hydrazides such as (E)-N’-[4-{2-(4-fluorophenylthio)ethoxy}-3-cyano-5-methoxybenzylidene]-2,5-dichlorobenzohydrazide (8.6), (E)-N’-[4-{2-(4-fluorophenylthio)ethoxy}-3-cyano-5-methoxybenzylidene]-2,5-difluorobenzohydrazide (8.9) showed duplication of NMR signals, this was attributed to the presence of anti and syn periplanar conformers. Antibacterial study against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa with reference to the standard drug (streptomycin) revealed that compounds bearing R = 4-OH (8.2), 3,4,5-OMe (8.3) and 4-SO₂Me (8.4) substituents has shown the good antibacterial sensitivity.

Keywords

Substituted benzohydrazide derivatives Vanillin

Dommati, L., Satyanarayana, B., Hela, P. G., Ram, B., & Srinivas, G. (2016). Synthesis and Antibacterial Activity of (E)-N’-[4-{2-(4-Fluorophenylthio)ethoxy}-3-cyano-5-methoxybenzylidene]-substituted benzohydrazide Derivatives. Asian Journal of Chemistry, 28(7), 1584–1588. https://doi.org/10.14233/ajchem.2016.19776

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References

N.J. Walton, M.J. Mayer and A. Narbad, Phytochemistry, 63, 505 (2003); doi:10.1016/S0031-9422(03)00149-3.

D.J. Fitzgerald, M. Stratford and A. Narbad, Int. J. Food Microbiol., 86, 113 (2003); doi:10.1016/S0168-1605(03)00059-X.

Y. Vaghasiya, R. Nair, M. Soni, S. Baluja and S. Shanda, J. Serb. Chem. Soc., 69, 991 (2004); doi:10.2298/JSC0412991V.

S. Rakchoy, P. Suppakul and T. Jinkarn, Asian J. Food. Agro-Ind., 2, 138 (2009).

H. Imanishi, Y. Sasaki, K. Matsumoto, M. Watanabe, T. Ohta, Y. Shirasu and K. Tutikawa, Mutat. Res. Lett., 243, 151 (1990); doi:10.1016/0165-7992(90)90038-L.

T. Ohta, M. Watanabe, K. Watanabe, Y. Shirasu and T. Kada, Food Chem. Toxicol., 24, 51 (1986); doi:10.1016/0278-6915(86)90264-4.

K. Ho, L.S. Yazan, N. Ismail and M. Ismail, Cancer Epidemiol., 33, 155 (2009); doi:10.1016/j.canep.2009.06.003.

T.T. Nguyen, A. Iwaki, Y. Ohya and S. Izawa, J. Biosci. Bioeng., 117, 33 (2014); doi:10.1016/j.jbiosc.2013.06.008.

S. Rollas and S.G. Kücükgüzel, Molecules, 12, 1910 (2007); doi:10.3390/12081910.

R. Narang, B. Narasimhan and S. Sharma, Curr. Med. Chem., 19, 569 (2012); doi:10.2174/092986712798918789.

P.P.T. Sah and S.A. Peoples, J. Am. Pharm. Assoc., 43, 513 (1954); doi:10.1002/jps.3030430902.

D. Chakravarty, A. Bose and S.J. Bose, J. Pharm. Sci., 53, 1036 (1964); doi:10.1002/jps.2600530911.

A. Gürsoy, N. Terzioglu and G. Ötük, Eur. J. Med. Chem., 32, 753 (1997); doi:10.1016/S0223-5234(97)88918-0.

P. Vicini, F. Zani, P. Cozzini and I. Doytchinova, Eur. J. Med. Chem., 37, 553 (2002); doi:10.1016/S0223-5234(02)01378-8.

P. Kumar, B. Narasimhan, D. Sharma, V. Judge and R. Narang, Eur. J. Med. Chem., 44, 1853 (2009); doi:10.1016/j.ejmech.2008.10.034.

N. Terzioglu and A. Gürsoy, Eur. J. Med. Chem., 38, 781 (2003); doi:10.1016/S0223-5234(03)00138-7.

B. Zhang, Y. Zhao, X. Zhai, L. Wang, J. Yang, Z. Tan and P. Gong, Chem. Pharm. Bull. (Tokyo), 60, 1046 (2012); doi:10.1248/cpb.c12-00234.

Y. Xia, C.D. Fan, B.X. Zhao, J. Zhao, D.S. Shin and J.Y. Miao, Eur. J. Med. Chem., 43, 2347 (2008); doi:10.1016/j.ejmech.2008.01.021.

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A.H. Collins, Microbiological Methods, Butterworth, London, edn 2 (1976).

Ch. Krishna Prasad and P.V.S Machi Raju, J. Applicable Chem., 3, 1460 (2014).

D. Subramanyam, B. Balram, B. Ram and B. Taara, Der Pharma Chemica, 4, 2239 (2012).

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V.M. Rahman, S. Mukhtar, W.H. Ansari and G. Lemiere, Eur. J. Med. Chem., 40, 173 (2005); doi:10.1016/j.ejmech.2004.10.003.

B. Tian, M. He, S. Tang, I. Hewlett, Z. Tan, J. Li, Y. Jin and Y. Yang, Bioorg. Med. Chem. Lett., 19, 2162 (2009); doi:10.1016/j.bmcl.2009.02.116.

A. Quattropani, J. Dorbais, D. Covini, P.A. Pittet, V. Colovray, R.J. Thomas, R. Coxhead, S. Halazy, A. Scheer, M. Missotten, G. Ayala, C. Bradshaw, A.-M. De Raemy-Schenk, A. Nichols, R. Cirillo, E.G. Tos, C. Giachetti, L. Golzio, P. Marinelli, D.J. Church, C. Barberis, A. Chollet and M.K. Schwarz, J. Med. Chem., 48, 7882 (2005); doi:10.1021/jm050645f.

Issue

Vol. 28 No. 7 (2016): Vol 28 Issue 7

Synthesis and Antibacterial Activity of (E)-N'-[4-{2-(4-Fluorophenylthio)ethoxy}-3-cyano-5-methoxybenzylidene]-substituted benzohydrazide Derivatives

Corresponding Author(s) : Lokamaheshwari Dommati

Abstract

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