European Journal of Chemistry 2011, 2(2), 238-242. doi:https://doi.org/10.5155/eurjchem.2.2.238-242.206

Synthesis and anti-tubercular activity of novel pyrazol-5(H)-one derivatives


Jignesh Priyakant Raval (1,*) , Arpita Bharatbhai Shah (2) , Nilesh Hasmukhbhai Patel (3) , Hemul Venubhai Patel (4) , Pradip Shantilal Patel (5) , Kashyap Kanaiyalal Bhatt (6) , Kishor Ratilal Desai (7)

(1) Department of Pharmaceutical Chemistry, Ashok and Rita Patel Institute of Integrated Study and Research in Biotechnology and Allied Sciences, New Vallabh Vidyanagar, Anand, Gujarat, 388121, India
(2) Department of Pharmaceutical Chemistry, Ashok and Rita Patel Institute of Integrated Study and Research in Biotechnology and Allied Sciences, New Vallabh Vidyanagar, Anand, Gujarat, 388121, India
(3) Department of Pharmaceutical Chemistry, Ashok and Rita Patel Institute of Integrated Study and Research in Biotechnology and Allied Sciences, New Vallabh Vidyanagar, Anand, Gujarat, 388121, India
(4) Department of Pharmaceutical Chemistry, Ashok and Rita Patel Institute of Integrated Study and Research in Biotechnology and Allied Sciences, New Vallabh Vidyanagar, Anand, Gujarat, 388121, India
(5) Department of Pharmaceutical Chemistry, Ashok and Rita Patel Institute of Integrated Study and Research in Biotechnology and Allied Sciences, New Vallabh Vidyanagar, Anand, Gujarat, 388121, India
(6) Department of Pharmaceutical Chemistry, Indukaka Ipcowala College of Pharmacy, New Vallabh Vidyanagar, Anand, Gujarat, 38121, India
(7) C. G. Bhakta Institute of Biotechnology, Gopal Vidynagar, Tarsadi, Surat, Gujarat, 394350, India
(*) Corresponding Author

Received: 14 Jul 2010, Accepted: 14 Nov 2010, Published: 30 Jun 2011

Abstract


In the present investigation, a series of 1-isonicotinoyl-3-methyl-4-(2-(substituted-phenyl)hydrazono)-1H-pyrazol-5(H)-ones were synthesized by the reaction between isonicotinohydrazide with substituted ethylacetoacetate derivatives using acetic acid as solvent which yielded substituted pyrazol-5(H)-one derivatives. Newly synthesized compounds were tested for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the synthesized compounds, 4-(2-(2,6-dichlorophenyl)hydrazono)-1-isonicotinoyl-3-methyl-1H-pyrazol-5(4H)-one and 4-(2-(1-isonicotinoyl-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)hydrazinyl) benzene-sulfonamide were found to be more active agent against M. tuberculosis H37Rv with minimum inhibitory concentration of 0.0034, 0.0032 µM at actual MIC 1.66 and 1.64 µg/mL, respectively.

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Keywords


Isonicotinohydrazide; Pyrazol-5(H)-ones; Anti-tubercular activity; Anti-mycobacterial activity; Mycobacterium tuberculosis; M. tuberculosis H37Rv

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DOI: 10.5155/eurjchem.2.2.238-242.206

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[1]. M. Kumar, V. Kumar, V. Beniwal
Synthesis of some pyrazolylaldehyde N-isonicotinoyl hydrazones and 2,5-disubstituted 1,3,4-oxadiazoles as DNA photocleaving agents
Medicinal Chemistry Research  24(7), 2862, 2015
DOI: 10.1007/s00044-015-1340-x
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[2]. M. Kumar, V. Kumar, G. K. Gupta
Synthesis, antibacterial evaluation, and SAR study of some novel 3-aryl/heteroaryl-9-methyl-1,2,4-triazolo-[4,3-a]-quinoline derivatives
Medicinal Chemistry Research  24(5), 1857, 2015
DOI: 10.1007/s00044-014-1254-z
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[3]. Ahmed Abdou O. Abeed
2-Pyrazolin-5-One-Based Heterocycles: Synthesis and Characterization
Journal of Heterocyclic Chemistry  52(4), 1175, 2015
DOI: 10.1002/jhet.2225
/


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How to cite


Raval, J.; Shah, A.; Patel, N.; Patel, H.; Patel, P.; Bhatt, K.; Desai, K. Eur. J. Chem. 2011, 2(2), 238-242. doi:https://doi.org/10.5155/eurjchem.2.2.238-242.206
Raval, J.; Shah, A.; Patel, N.; Patel, H.; Patel, P.; Bhatt, K.; Desai, K. Eur. J. Chem. Synthesis and anti-tubercular activity of novel pyrazol-5(H)-one derivatives. 2011, 2(2), 238-242. doi:https://doi.org/10.5155/eurjchem.2.2.238-242.206
Raval, J., Shah, A., Patel, N., Patel, H., Patel, P., Bhatt, K., & Desai, K. (2011). Synthesis and anti-tubercular activity of novel pyrazol-5(H)-one derivatives. European Journal of Chemistry, 2(2), 238-242. doi:https://doi.org/10.5155/eurjchem.2.2.238-242.206
Raval, Jignesh, Arpita Bharatbhai Shah, Nilesh Hasmukhbhai Patel, Hemul Venubhai Patel, Pradip Shantilal Patel, Kashyap Kanaiyalal Bhatt, & Kishor Ratilal Desai. "Synthesis and anti-tubercular activity of novel pyrazol-5(H)-one derivatives." European Journal of Chemistry [Online], 2.2 (2011): 238-242. Web. 18 Jun. 2018
Raval, Jignesh, Shah, Arpita, Patel, Nilesh, Patel, Hemul, Patel, Pradip, Bhatt, Kashyap, AND Desai, Kishor. "Synthesis and anti-tubercular activity of novel pyrazol-5(H)-one derivatives" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)

DOI: https://doi.org/10.5155/eurjchem.2.2.238-242.206

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