Novel Acetohydrazide Pyrazole Derivatives: Design, Synthesis, Characterization and Antimicrobial Activity

Anil Verma; Vinod Kumar; Ramesh Kataria; Joginder Singh

doi:10.14233/ajchem.2019.22190

Issue

Vol. 31 No. 12 (2019): Vol 31 Issue 12

Issue Published : November 16, 2019

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

Novel Acetohydrazide Pyrazole Derivatives: Design, Synthesis, Characterization and Antimicrobial Activity

https://doi.org/10.14233/ajchem.2019.22190

Anil Verma

Department of Chemistry, Maharishi Markandeshwar University (Deemed to be University), Mullana-133201, India

Vinod Kumar

Department of Chemistry, Maharishi Markandeshwar University (Deemed to be University), Mullana-133201, India & Department of Chemistry, Central University of Haryana, Mahendergarh-123031, India

Ramesh Kataria

Department of Chemistry, Panjab University, Chandigarh-160014, India

Joginder Singh

Department of Chemistry, Maharishi Markandeshwar University (Deemed to be University), Mullana-133201, India

Corresponding Author(s) : Joginder Singh

joginderchem@mmumullana.org

Asian Journal of Chemistry, Vol. 31 No. 12 (2019): Vol 31 Issue 12
Article Published : November 16, 2019

Abstract

Eleven acetohydrazide linked pyrazole derivatives were designed and synthesized via condensation of acetohyadrazide with different substituted formyl pyrazole derivatives under mild reaction conditions. Synthesized compounds were characterized on the basis of IR, NMR (¹H & ¹³C) and mass spectrometry. The antimicrobial activities of all the compounds were screened against four bacterial and two fungal strains. Among the synthesized compounds, three compounds viz. 6b, 6c and 6d were found as efficient antimicrobial agents in reference to the standard drugs viz. ciprofloxacin and amphotericin-B. Further, structure-activity relationship (SAR) study revealed that electron-withdrawing group enhances the antimicrobial potential of synthesized derivatives as compared to other groups present in the ring. Hence, among compounds 6b-c, compound 6d could be explored further against other microbes to prove its vitality.

Keywords

Acetohydrazide pyrazoles Antimicrobial activity.

Verma, A., Kumar, V., Kataria, R., & Singh, J. (2019). Novel Acetohydrazide Pyrazole Derivatives: Design, Synthesis, Characterization and Antimicrobial Activity. Asian Journal of Chemistry, 31(12), 2740–2744. https://doi.org/10.14233/ajchem.2019.22190

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References

R. Basawaraj, B. Yadav and S.S. Sangapure, Indian J. Heterocycl. Chem., 11, 31 (2001).
S.M. Rida, S.A.M. El-Hawash, H.T.Y. Fahmy, A.A. Hazzaa and M.M.M. El-Meligy, Arch. Pharm. Res., 29, 826 (2006); https://doi.org/10.1007/BF02973901.
R.K. Ujjinamatada, R.S. Appala and Y.S. Agasimundin, J. Heterocycl. Chem., 43, 437 (2006); https://doi.org/10.1002/jhet.5570430226.
S. Wachi, K. Takagi, G. Menichi and M. Hubert-Habart, Bull. Soc. Chim. Fr., 5-6, 230 (1978).
D.V. Singh, A.R. Mishra, R.M. Mishra, A.K. Pandey, C.R. Singh and A.K. Dwivedi, Indian J. Heterocycl. Chem., 14, 319 (2005).
J.U. Cho and C.J. Kim H.B. Lee and C.H. Lim, Patent Korea KR 2004064795 (2004); Chem. Abstr., 145, 182279 (2004).
P. Druzgala and P.G. Milner, Novel Enantiomeric Compounds for Treatment of Cardiac Arrhythmias and Methods of Use, U.S. Patent 20020193428 (2002).
K.M. Dawood, H. Abdel-Gawad, E.A. Rageb, M. Ellithey and H.A. Mohamed, Bioorg. Med. Chem., 14, 3672 (2006); https://doi.org/10.1016/j.bmc.2006.01.033.
P.D. Sauzem, P. Machado, M.A. Rubin, G. da S. Sant’Anna, H.B. Faber, A.H. de Souza, C.F. Mello, P. Beck, R.A. Burrow, H.G. Bonacorso, N. Zanatta and M.A.P. Martins, Eur. J. Med. Chem., 43, 1237 (2008);https://doi.org/10.1016/j.ejmech.2007.07.018.
A. Hall, A. Billinton, S.H. Brown, N.M. Clayton, A. Chowdhury, G.M.P. Giblin, P. Goldsmith, T.G. Hayhow, D.N. Hurst, I.R. Kilford, A. Naylor, B. Passingham and L. Winyard, Bioorg. Med. Chem. Lett., 18, 3392 (2008); https://doi.org/10.1016/j.bmcl.2008.04.018.
F.R. Souza, V.T. Souza, V. Ratzlaff, L.P. Borges, M.R. Oliveira, H.G. Bonacorso, N. Zanatta, M.A.P. Martins and C.F. Mello, Eur. J. Pharm, 451, 141 (2002); https://doi.org/10.1016/S0014-2999(02)02225-2.
M. Iovu, C. Zalaru, F. Dumitrascu, C.M. Draghici, M. Moraru and E. Cristea, IL Farmaco, 58, 301 (2003); https://doi.org/10.1016/S0014-827X(02)00014-9.
F. Manna, F. Chimenti, A. Bolasco, D. Secci, B. Bizzarri, O. Befani, P. Turini, B. Mondovi’, S. Alcaro and A. Tafi, Bioorg. Med. Chem. Lett., 12, 3629 (2002); https://doi.org/10.1016/S0960-894X(02)00699-6.
X.-D. Yang, J. Chem. Res., 2008, 489 (2008); https://doi.org/10.3184/030823408X340799.
A. Verma, V. Kumar, R. Khare and J. Singh, Asian J. Chem., 31, 522 (2019); https://doi.org/10.14233/ajchem.2019.21671.
K. Kaur, V. Kumar, V. Beniwal, V. Kumar, K.R. Aneja, V. Sharma and S. Jaglan, Med. Chem. Res., 24, 3863 (2015); https://doi.org/10.1007/s00044-015-1429-2.
I. Gulcin, A.Z. Tel and E. Kirecci, Int. J. Food Prop., 11, 450 (2008); https://doi.org/10.1080/10942910701567364.
I. Glucin, E. Kirecci, E. Akkemik, F. Topel and O. Hisar, Turk. J. Biol., 34, 175 (2010).

References

R. Basawaraj, B. Yadav and S.S. Sangapure, Indian J. Heterocycl. Chem., 11, 31 (2001).

S.M. Rida, S.A.M. El-Hawash, H.T.Y. Fahmy, A.A. Hazzaa and M.M.M. El-Meligy, Arch. Pharm. Res., 29, 826 (2006); https://doi.org/10.1007/BF02973901.

R.K. Ujjinamatada, R.S. Appala and Y.S. Agasimundin, J. Heterocycl. Chem., 43, 437 (2006); https://doi.org/10.1002/jhet.5570430226.

S. Wachi, K. Takagi, G. Menichi and M. Hubert-Habart, Bull. Soc. Chim. Fr., 5-6, 230 (1978).

D.V. Singh, A.R. Mishra, R.M. Mishra, A.K. Pandey, C.R. Singh and A.K. Dwivedi, Indian J. Heterocycl. Chem., 14, 319 (2005).

J.U. Cho and C.J. Kim H.B. Lee and C.H. Lim, Patent Korea KR 2004064795 (2004); Chem. Abstr., 145, 182279 (2004).

P. Druzgala and P.G. Milner, Novel Enantiomeric Compounds for Treatment of Cardiac Arrhythmias and Methods of Use, U.S. Patent 20020193428 (2002).

K.M. Dawood, H. Abdel-Gawad, E.A. Rageb, M. Ellithey and H.A. Mohamed, Bioorg. Med. Chem., 14, 3672 (2006); https://doi.org/10.1016/j.bmc.2006.01.033.

P.D. Sauzem, P. Machado, M.A. Rubin, G. da S. Sant’Anna, H.B. Faber, A.H. de Souza, C.F. Mello, P. Beck, R.A. Burrow, H.G. Bonacorso, N. Zanatta and M.A.P. Martins, Eur. J. Med. Chem., 43, 1237 (2008);https://doi.org/10.1016/j.ejmech.2007.07.018.

A. Hall, A. Billinton, S.H. Brown, N.M. Clayton, A. Chowdhury, G.M.P. Giblin, P. Goldsmith, T.G. Hayhow, D.N. Hurst, I.R. Kilford, A. Naylor, B. Passingham and L. Winyard, Bioorg. Med. Chem. Lett., 18, 3392 (2008); https://doi.org/10.1016/j.bmcl.2008.04.018.

F.R. Souza, V.T. Souza, V. Ratzlaff, L.P. Borges, M.R. Oliveira, H.G. Bonacorso, N. Zanatta, M.A.P. Martins and C.F. Mello, Eur. J. Pharm, 451, 141 (2002); https://doi.org/10.1016/S0014-2999(02)02225-2.

M. Iovu, C. Zalaru, F. Dumitrascu, C.M. Draghici, M. Moraru and E. Cristea, IL Farmaco, 58, 301 (2003); https://doi.org/10.1016/S0014-827X(02)00014-9.

F. Manna, F. Chimenti, A. Bolasco, D. Secci, B. Bizzarri, O. Befani, P. Turini, B. Mondovi’, S. Alcaro and A. Tafi, Bioorg. Med. Chem. Lett., 12, 3629 (2002); https://doi.org/10.1016/S0960-894X(02)00699-6.

X.-D. Yang, J. Chem. Res., 2008, 489 (2008); https://doi.org/10.3184/030823408X340799.

A. Verma, V. Kumar, R. Khare and J. Singh, Asian J. Chem., 31, 522 (2019); https://doi.org/10.14233/ajchem.2019.21671.

K. Kaur, V. Kumar, V. Beniwal, V. Kumar, K.R. Aneja, V. Sharma and S. Jaglan, Med. Chem. Res., 24, 3863 (2015); https://doi.org/10.1007/s00044-015-1429-2.

I. Gulcin, A.Z. Tel and E. Kirecci, Int. J. Food Prop., 11, 450 (2008); https://doi.org/10.1080/10942910701567364.

I. Glucin, E. Kirecci, E. Akkemik, F. Topel and O. Hisar, Turk. J. Biol., 34, 175 (2010).

Issue

Vol. 31 No. 12 (2019): Vol 31 Issue 12

Novel Acetohydrazide Pyrazole Derivatives: Design, Synthesis, Characterization and Antimicrobial Activity

Corresponding Author(s) : Joginder Singh

Abstract

Keywords

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