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Synthesis and Antimicrobial Activity of New Imidazole-Hydrazone Derivatives
Corresponding Author(s) : V. Laxmi Prasanna
Asian Journal of Chemistry,
Vol. 27 No. 10 (2015): Vol 27 Issue 10
Abstract
Hydrazones demonstrated significant antimicrobial activity, antitubercular activity and antitumoral activity in medicinal areas. The imidazole nucleus is well known to play an important role in living organisms since it is incorporated into the histidine molecule and many other important biological, pharmacological and therapeutic activities. Condensation of 4-phenyl-1H-imidazole-2-carbaldehyde (3) with various selected benzohydrazides (4a-m) resulted in imidazole-hydrazone derivatives (5a-m). They were evaluated for antibacterial and antifungal activity against A. niger, C. albicans (fungal strains), E. coli and P. aeruginosa (Gram-negative bacteria), S. aureus and S. pyogenes (Gram-positive bacteria) using griseofluvin (for fungi) and ciprofloxacin (for bacteria) as the standard drugs. In general, it is observed that most of the compounds were found to be potent against both the bacterial and fungal strains.
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- J.G. Lombardino and E.H. Wiseman, J. Med. Chem., 17, 1182 (1974); doi:10.1021/jm00257a011.
- J.G. Lombardino, Ger. Offen. 2,155,558 (1972); Chem. Abstr., 77, 101607y (1972).
- A.P. Phillips, H.L. White and S. Rosen, Eur. Pat. Appl. EP, 58,890 (1982); Chem. Abstr., 98, 53894z (1983).
- J.C. Lee, J.T. Laydon, P.C. McDonnell, T.F. Gallagher, S. Kumar, D. Green, D. McNulty, M.J. Blumenthal, J.R. Keys, S.W. Land vatter, J.E. Strickler, M.M. McLaughlin, I.R. Siemens, S.M. Fisher, G.P. Livi, J.R. White, J.L. Adams and P.R. Young, Nature, 372, 739 (1994); doi:10.1038/372739a0.
- A.S. Bell, in eds.: D.S. Jonhson and J.J. Li, The Art of Drug Synthesis; John Wiley & Sons, Inc.: Hoboken, NJ, USA, pp. 72–73 (2007).
- B. Narasimhan, D. Sharma and P. Kumar, Med. Chem. Res., 20, 1119 (2011); doi:10.1007/s00044-010-9472-5.
- S.G. Kucukguzel, E.E. Oruç, S. Rollas, F. Şahin and A. Özbek, Eur. J. Med. Chem., 37, 197 (2002); doi:10.1016/S0223-5234(01)01326-5.
- S. Rollas, N. Gülerman and H. Erdeniz, Farmaco, 57, 171 (2002); doi:10.1016/S0014-827X(01)01192-2.
- L. Savini, L. Chiasserini, V. Travagli, C. Pellerano, E. Novellino, S. Cosentino and M.B. Pisano, Eur. J. Med. Chem., 39, 113 (2004); doi:10.1016/j.ejmech.2003.09.012.
- D. Young, S. Shaber, C. Avila-Adame, N. Breaux, J. Ruiz, T. Siddall and J. Webster, WO2010083319 (2010); Chem. Abstr., 153, 204054 (2010).
- X.D. Yang, J. Chem. Res., 489 (2008); doi:10.3184/030823408X340799.
- T. Okuno, I. Furusawa, K. Matsuura and J. Shishiyama, Phytopathology, 79, 827 (1989); doi:10.1094/Phyto-79-827.
- A.B. Samel and N.R. Pai, J. Chem. Pharm. Res, 2, 60 (2010).
- S.A.M. Shedid, H.M. Hassan and F.A. Kora, J. Chem. Pharm. Res., 3, 388 (2011).
- D. Kaushik, S.A. Khan, G. Chawla and S. Kumar, Eur. J. Med. Chem., 45, 3943 (2010); doi:10.1016/j.ejmech.2010.05.049.
- S. Han, F.-F. Zhang, X. Xie and J.-Z. Chei, Eur. J. Med. Chem., 74, 73 (2014); doi:10.1016/j.ejmech.2013.12.018.
- B.R. Dekic, N.S. Radulovic, V.S. Dekic, R.D. Vukićevic and R.M. Palic, Molecules, 15, 2246 (2010); doi:10.3390/molecules15042246.
- E.S. Coimbra, L.M.R. Antinarelli, A.D. Da Silva, M.L.F. Bispo, C.R. Kaiser and M.V.N. De Souza, Chem. Biol. Drug Des., 81, 658 (2013); doi:10.1111/cbdd.12112.
- P. Vicini, M. Incerti, I.A. Doytchinova, P. La Colla, B. Busonera and R. Loddo, Eur. J. Med. Chem., 41, 624 (2006); doi:10.1016/j.ejmech.2006.01.010.
References
J.G. Lombardino and E.H. Wiseman, J. Med. Chem., 17, 1182 (1974); doi:10.1021/jm00257a011.
J.G. Lombardino, Ger. Offen. 2,155,558 (1972); Chem. Abstr., 77, 101607y (1972).
A.P. Phillips, H.L. White and S. Rosen, Eur. Pat. Appl. EP, 58,890 (1982); Chem. Abstr., 98, 53894z (1983).
J.C. Lee, J.T. Laydon, P.C. McDonnell, T.F. Gallagher, S. Kumar, D. Green, D. McNulty, M.J. Blumenthal, J.R. Keys, S.W. Land vatter, J.E. Strickler, M.M. McLaughlin, I.R. Siemens, S.M. Fisher, G.P. Livi, J.R. White, J.L. Adams and P.R. Young, Nature, 372, 739 (1994); doi:10.1038/372739a0.
A.S. Bell, in eds.: D.S. Jonhson and J.J. Li, The Art of Drug Synthesis; John Wiley & Sons, Inc.: Hoboken, NJ, USA, pp. 72–73 (2007).
B. Narasimhan, D. Sharma and P. Kumar, Med. Chem. Res., 20, 1119 (2011); doi:10.1007/s00044-010-9472-5.
S.G. Kucukguzel, E.E. Oruç, S. Rollas, F. Şahin and A. Özbek, Eur. J. Med. Chem., 37, 197 (2002); doi:10.1016/S0223-5234(01)01326-5.
S. Rollas, N. Gülerman and H. Erdeniz, Farmaco, 57, 171 (2002); doi:10.1016/S0014-827X(01)01192-2.
L. Savini, L. Chiasserini, V. Travagli, C. Pellerano, E. Novellino, S. Cosentino and M.B. Pisano, Eur. J. Med. Chem., 39, 113 (2004); doi:10.1016/j.ejmech.2003.09.012.
D. Young, S. Shaber, C. Avila-Adame, N. Breaux, J. Ruiz, T. Siddall and J. Webster, WO2010083319 (2010); Chem. Abstr., 153, 204054 (2010).
X.D. Yang, J. Chem. Res., 489 (2008); doi:10.3184/030823408X340799.
T. Okuno, I. Furusawa, K. Matsuura and J. Shishiyama, Phytopathology, 79, 827 (1989); doi:10.1094/Phyto-79-827.
A.B. Samel and N.R. Pai, J. Chem. Pharm. Res, 2, 60 (2010).
S.A.M. Shedid, H.M. Hassan and F.A. Kora, J. Chem. Pharm. Res., 3, 388 (2011).
D. Kaushik, S.A. Khan, G. Chawla and S. Kumar, Eur. J. Med. Chem., 45, 3943 (2010); doi:10.1016/j.ejmech.2010.05.049.
S. Han, F.-F. Zhang, X. Xie and J.-Z. Chei, Eur. J. Med. Chem., 74, 73 (2014); doi:10.1016/j.ejmech.2013.12.018.
B.R. Dekic, N.S. Radulovic, V.S. Dekic, R.D. Vukićevic and R.M. Palic, Molecules, 15, 2246 (2010); doi:10.3390/molecules15042246.
E.S. Coimbra, L.M.R. Antinarelli, A.D. Da Silva, M.L.F. Bispo, C.R. Kaiser and M.V.N. De Souza, Chem. Biol. Drug Des., 81, 658 (2013); doi:10.1111/cbdd.12112.
P. Vicini, M. Incerti, I.A. Doytchinova, P. La Colla, B. Busonera and R. Loddo, Eur. J. Med. Chem., 41, 624 (2006); doi:10.1016/j.ejmech.2006.01.010.