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Short Note

Synthesis of 3-[2-(4-Chlorobenzylidene)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), M597; https://doi.org/10.3390/M597
Submission received: 25 January 2009 / Accepted: 19 March 2009 / Published: 23 March 2009
Versions Notes

Abstract

:
3-Hydrazino-3-oxo-N-(4-sulfamoylphenyl)propanamide has been used as a synthon for the preparation of 3-[2-(4-chlorobenzylidene)hydrazino]-3-oxo-N-(4-sulfamoylphenyl)propanamide.

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]. Hydrazide-hydrazones have been reported to possess a wide variety of pharmacological activities such as anti-bacterial [2,3], anti-convulsant [4], anti-inflammatory [5], anti-tubercular [6], intestinal antiseptic [2], anti-depressant [7], or anti-platelet activity [8]. The aroyl hydrazone chelator, 2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone, showed greater anti-malarial activity than desferrioxamine against chloroquine-resistant and sensitive parasites [9]. 3- and 5-methylthiophene-2-carboxaldehyde-α-(N)-heterocyclic hydrazone derivatives exhibited tumor growth inhibition activity against various cell lines at GI50 values between 1.63 and 26.5 μM [10]. Hydrazones are often mentioned among the most effective charge transporting low molecular weight materials used in electrophotography, due to their excellent hole-transporting properties and relatively simple synthesis [11,12,13,14].
These properties prompted us to synthesize this new malonamic acid hydrazone shown below.
Molbank 2009 m597 i001
A mixture of 3-Hydrazino-3-oxo-N-(4-sulfamoylphenyl)propanamide (I) [15] (0.272 g, 0.001 mol) and 4-chlorobenzaldehyde (II) (0.140 g, 0.001 mol) in absolute ethanol (10 ml) was gently refluxed for two hours. 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-[2-(4-Chlorobenzylidene)hydrazino]-3-oxo-N-(4-sulfamoylphenyl)propanamide (III). Yield: 81.3%
M.p. 162oC
IR (KBr): 3301, 3022, 2932, 1647, 1537, 1363, 1049, 670 cm–1.
1H-NMR (300 MHz, DMSO-d6): δ 4.23 (s, 2H, -NH2), 3.32 (s, 2H, -CH2), 7.49-7.97 (m, 8H, Ar-H), 8.37 (s, 1H, -CONH), 8.71 (s, 1H, -CH), 9.04 (s, 1H, -CONH).
MS: Base peak m/z 377.
Elemental analysis:
Calcd for C16H15N4O4SCl (394.5): C, 48.66%; H, 3.80%; N, 14.19%.
Found: C, 48.69%; H, 3.76 %; N, 14.21%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgement

The authors thank the Central Drug Research Institute (CDRI), Lucknow for spectral and elemental analysis.

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 3-[2-(4-Chlorobenzylidene)hydrazino]-3-oxo-N-(4-sulfamoylphenyl)propanamide. Molbank 2009, 2009, M597. https://doi.org/10.3390/M597

AMA Style

Naqvi A, Shahnawaaz M, Rao AV, Seth DS, Sharma NK. Synthesis of 3-[2-(4-Chlorobenzylidene)hydrazino]-3-oxo-N-(4-sulfamoylphenyl)propanamide. Molbank. 2009; 2009(1):M597. https://doi.org/10.3390/M597

Chicago/Turabian Style

Naqvi, Arshi, Mohd. Shahnawaaz, Arikatla V. Rao, Daya S. Seth, and Nawal K. Sharma. 2009. "Synthesis of 3-[2-(4-Chlorobenzylidene)hydrazino]-3-oxo-N-(4-sulfamoylphenyl)propanamide" Molbank 2009, no. 1: M597. https://doi.org/10.3390/M597

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