in vitro Antimicrobial Activity and in silico Activity of 1-Thiocarbamoyl Substituted Pyrazole Derivatives

Raja Chinnamanayakar; M.R. Ezhilarasi; B. Prabha; Kulandhaivel

doi:10.14233/ajchem.2018.20992

Issue

Vol. 30 No. 4 (2018): Vol 30 Issue 4

Issue Published : February 28, 2018

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

in vitro Antimicrobial Activity and in silico Activity of 1-Thiocarbamoyl Substituted Pyrazole Derivatives

https://doi.org/10.14233/ajchem.2018.20992

Raja Chinnamanayakar

Department of Chemistry, Karpagam Academy of Higher Education, Eachanari, Coimbatore-641 021, India

M.R. Ezhilarasi

Department of Chemistry, Karpagam Academy of Higher Education, Eachanari, Coimbatore-641 021, India

B. Prabha

Department of Chemistry, Karpagam Academy of Higher Education, Eachanari, Coimbatore-641 021, India

Kulandhaivel

Department of Microbiology, Karpagam Academy of Higher Education, Eachanari, Coimbatore-641 021, India

Corresponding Author(s) : M.R. Ezhilarasi

ezhilarasi.au@gmail.com

Asian Journal of Chemistry, Vol. 30 No. 4 (2018): Vol 30 Issue 4
Article Published : February 28, 2018

Abstract

A convenient synthesis of 1-thiocarbamoyl-3-phenyl-5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives (2a-2g) was carried out by the condensation reaction of (E)-3-(phenyl)-1-(biphenyl-2-yl)-3-arylprop-2-en-1-ones (1a-1g) with thiosemicarbazide, sodium hydroxide as a catalyst in the presence of ethanol as solvent. Further, (E)-3-(phenyl)-1-(biphenyl-2-yl)-3-arylprop-2-en-1-ones were synthesized by the Claisen-Schmidt condensation reaction of substituted aldehydes with 4-acetylbiphenyl in the presence of basic ethanolic solution. The structure of synthesized compounds were confirmed by FT-IR, ¹H NMR, ¹³C NMR and ¹H-¹H COSY. The antimicrobial susceptibility tests of synthesized compounds were screened against Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Pseudomonas aeruginosa. The docking studies also carried out by using 1UAG receptor for all the synthesized compounds (2a-2g).

Keywords

4-Acetyl biphenyl chalcone Thiosemicarbazide Antimicrobial activity Molecular docking studies

Chinnamanayakar, R., Ezhilarasi, M., Prabha, B., & Kulandhaivel, . (2018). in vitro Antimicrobial Activity and in silico Activity of 1-Thiocarbamoyl Substituted Pyrazole Derivatives. Asian Journal of Chemistry, 30(4), 783–789. https://doi.org/10.14233/ajchem.2018.20992

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References

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M. Rani, M. Yusuf and S.A. Khan, J. Saudi Chem. Soc., 16, 431 (2012); https://doi.org/10.1016/j.jscs.2011.02.012.

K.S. Atwal, G.C. Rovnyak, S.D. Kimball, D.M. Floyd, S. Moreland, B.N. Swanson, J.Z. Gougoutas, J. Schwartz, K.M. Smillie and M.F. Malley, J. Med. Chem., 33, 2629 (1990); https://doi.org/10.1021/jm00171a044.

K.S. Nimavat, K.H. Popat, S.L. Vasoya and H.S. Joshi, Indian J. Heterocycl. Chem., 12, 217 (2003).

B.B. Chavan, A.S. Gadekar, P.P. Mehta, P.K. Vawhal, A.K. Kolsure and A.R. Chabukswar, Asian J. Biomed. Pharm. Sci., 6, 1 (2016).

A.R. Jalilian, S. Sattari, M. Bineshmarvasti, M. Daneshtalab and A. Shafiee, IL Farmaco, 58, 63 (2003); https://doi.org/10.1016/S0014-827X(02)00029-0.

A.R. Shafiee, B. Jalilian and M. Rezaei, J. Heterocycl. Chem., 37, 1325 (2000); https://doi.org/10.1002/jhet.5570370551.

A. Varvaresou, T. Siatra-Papastaikoudi, A. Tsotinis, A. TsantiliKakoulidou and A. Vamvakides, Farmaco, 53, 320 (1998); https://doi.org/10.1016/S0014-827X(98)00024-X.

M. Bineshmarvasti, M. Sharifzadeh, A.R. Jalilian, K. Soltaninejad and A. Shafiee, Daru, 11, 74 (2003).

P. Yogeeswari, N. Menon, A. Semwal, M. Arjun and D. Sriram, Eur. J. Med. Chem., 46, 2964 (2011); https://doi.org/10.1016/j.ejmech.2011.04.021.

N. Siddiqui and O. Singh, Indian J. Pharm. Sci., 65, 423 (2003).

C. Biot, B. Pradines, M.-H. Sergeant, J. Gut, P.J. Rosenthal and K. Chibale, Bioorg. Med. Chem., 17, 6434 (2007); https://doi.org/10.1016/j.bmcl.2007.10.003.

C. Shipman, S.H. Smith, J.C. Drach and D.L. Klayman, Antimicrob. Agents Chemother., 19, 682 (1981); https://doi.org/10.1128/AAC.19.4.682.

A. Siwek, J. Stefañska, K. Dzitko and A. Ruszczak, J. Mol. Model., 18, 4159 (2012); https://doi.org/10.1007/s00894-012-1420-5.

S. Singhal, S. Arora, S. Agarwal, R. Sharma and N. Singhal, World J. Pharm. Pharm. Sci., 2, 4661 (2013).

K.V. Hridhya and M. Kulandhaivel, Int. J. Pharmacog. Phytochem. Res., 9, 1001 (2017).

J.A. Bertrand, EMBO J., 16, 3416 (1997); https://doi.org/10.1093/emboj/16.12.3416.

Issue

Vol. 30 No. 4 (2018): Vol 30 Issue 4

in vitro Antimicrobial Activity and in silico Activity of 1-Thiocarbamoyl Substituted Pyrazole Derivatives

Corresponding Author(s) : M.R. Ezhilarasi

Abstract

Keywords

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