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Volume 2009
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Short Note

Synthesis of novel 3-Hydrazino-3-oxo-N-(4-sulfamoylphenyl)-propanamide

by
Arshi Naqvi
1,*,
Mohd. Shahnawaaz
1,
Arikatla V. Rao
1,
Daya S. Seth
1 and
Nawal K. Sharma
2
1
Department of Chemistry, School of Chemical Sciences, St. John's College, Agra-282002, India
2
Department of Bioengineering, University of Pittsburgh, 260 Kappa Drive, RIDC Park, Pittsburgh, PA 15234 , USA
*
Author to whom correspondence should be addressed.
Molbank 2009, 2009(1), M586; https://doi.org/10.3390/M586
Submission received: 27 November 2008 / Accepted: 12 December 2008 / Published: 15 January 2009
Versions Notes

Abstract

:
Novel 3-hydrazino-3-oxo-N-(4-sulfamoylphenyl)propanamide has been efficiently synthesized from DEM and hydrazine hydrate. The synthesized hydrazide was screened for anti-tubercular activity.

The full therapeutic possibilities of hydrazides were realized after the discovery of isonicotinic acid hydrazide (INH). Hydrazides and their derivatives have been described as useful synthons of various heterocyclic rings [1]. A large number of hydrazides and their derivatives are reported to possess a broad spectrum of biological activities [2,3,4,5,6,7,8,9,10,11,12,13,14,15]. Thus, these were found to be useful especially in the treatment of inflammatory and autoimmune diseases, osteoarthritis, respiratory diseases, tumors, cachexia, cardiovascular diseases, fever, hemorrhage and sepsis [11]. Hydrazides and derivatives exhibited antifungal [2], psychotropic [2], antituberculous [3,4,5,6], antiparasite [2,10], bacteriostatic [2,7,9,14], antiviral [14], insecticidal [15] and anti-cancer [16] activities.
These properties prompted us to synthesize this novel malonamic acid hydrazide. The synthesized hydrazide was screened for anti-tubercular activity against H37Rv employing REMA (Resazurin microtitre assay) method.
Molbank 2009 m586 i001
Sulphanilamide (8.6 g, 0.05 mol.) and freshly distilled diethyl malonate (16 ml, 0.1 mol) was gently refluxed in a round bottom flask using an upright air condenser for one hour and twenty minutes. After cooling, it was filtered. The filtrate was gently refluxed in 20 ml ethanol with 6 ml hydrazine hydrate (98%) in a round bottom flask on a boiling water bath for 45 minutes. On cooling, a white crystalline solid was obtained and it was purified by recrystallization from hot ethanol. On analysis, it was found to be 3-hydrazino-3-oxo-N-(4-sulfamoylphenyl)propanamide (yield = 86.96%).
M.P. 144oC
IR (KBr): 3285, 3020, 1604, 1522, 1476, 1336, 1215, 928 cm-1.
1H-NMR (300 MHz, DMSO-d6): δ 2.41 (s, 2H, -NH2), 2.91 (s, 2H, -NH2), 3.53 (s, 2H, -CH2), 4.43 (s, 1H, -NH), 7.18-7.84 (m, Ar-H), 8.39 (s, 1H, -NH).
Anti-tubercular screening: 3-Hydrazino-3-oxo-N-(4-sulfamoylphenyl)propanamide was tested at concentrations of 1.25, 2.5, 3.75, 5.0, 6.25, 7.5, 8.75 and 10.0 µg/ml. The title compound was not active at any of these concentrations.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The authors thank the Central Drug Research Institute (CDRI), Lucknow for spectral analysis and Dr. V. M. Katoch, Director and Pushpinder Singh, Jalma Institute of Leprosy and Other Micobacterial diseases, Agra for anti-tubercular screening.

References and Notes

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Share and Cite

MDPI and ACS Style

Naqvi, A.; Shahnawaaz, M.; Rao, A.V.; Seth, D.S.; Sharma, N.K. Synthesis of novel 3-Hydrazino-3-oxo-N-(4-sulfamoylphenyl)-propanamide. Molbank 2009, 2009, M586. https://doi.org/10.3390/M586

AMA Style

Naqvi A, Shahnawaaz M, Rao AV, Seth DS, Sharma NK. Synthesis of novel 3-Hydrazino-3-oxo-N-(4-sulfamoylphenyl)-propanamide. Molbank. 2009; 2009(1):M586. https://doi.org/10.3390/M586

Chicago/Turabian Style

Naqvi, Arshi, Mohd. Shahnawaaz, Arikatla V. Rao, Daya S. Seth, and Nawal K. Sharma. 2009. "Synthesis of novel 3-Hydrazino-3-oxo-N-(4-sulfamoylphenyl)-propanamide" Molbank 2009, no. 1: M586. https://doi.org/10.3390/M586

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