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 []. Hydrazide-hydrazones have been reported to possess a wide variety of pharmacological activities such as anti-bacterial [,], anti-convulsant [], anti-inflammatory [], anti-tubercular [], intestinal antiseptic [], anti-depressant [], or anti-platelet activity []. The aroyl hydrazone chelator, 2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone, showed greater anti-malarial activity than desferrioxamine against chloroquine-resistant and sensitive parasites []. 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 []. 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 [,,,].
These properties prompted us to synthesize this new malonamic acid hydrazone shown below.
A mixture of 3-Hydrazino-3-oxo-N-(4-sulfamoylphenyl)propanamide (I) [] (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 3Acknowledgement
The authors thank the Central Drug Research Institute (CDRI), Lucknow for spectral and elemental analysis.
References and Notes
- Polanc, S. Recent Application of Hydrazides and Related Compounds for the Synthesis of Heterocycles. Targets Heterocycl. Syst. 1999, 3, 33–91, [Chem. Abstr. 2000, 133, 237877u]. [Google Scholar]
- Rollas, S.; Gulerman, N.; Erdeniz, H. Synthesis and Antimicrobial Activity of Some New Hydrazones of 4-Fluorobenzoic Acid Hydrazide and 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines. Farmaco 2002, 57, 171–174. [Google Scholar] [CrossRef]
- Habib, N. S.; Issa, A. S.; Rida, S. M.; Ashour, F. A.; Tawil, G. G. Synthesis of Alkyloxybenzamide Derivatives as Potential Antimicrobial Agents. Pharmazie 1986, 41, 761–764. [Google Scholar] [PubMed]
- Dimmock, J. R.; Vashishtha, S. C.; Stables, J. P. Anticonvulsant Properties of Various Acetylhydrazones, Oxamoylhydrazones and Semicarbazones Derived from Aromatic and Unsaturated Carbonyl Compounds. Eur. J. Med. Chem. 2000, 35, 241–248. [Google Scholar] [CrossRef]
- Kalsi, R.; Pande, K.; Bhalla, T. N.; Barthwal, J. P.; Gupta, G. P.; Parmar, S. S. Antiinflammatory Activity of Quinazolinoformazans. J. Pharm. Sci. 1990, 79, 317–320. [Google Scholar] [CrossRef] [PubMed]
- Kucukguzel, S. G.; Mazi, A.; Sahin, F.; Ozturk, S.; Stables, J. Synthesis and Biological Activities of Diflunisal Hydrazide-hydrazones. Eur. J. Med. Chem. 2003, 38, 1005–1013. [Google Scholar] [CrossRef] [PubMed]
- Ergenç, N.; Günay, N. S. Synthesis and antidepressant evaluation of new 3-phenyl-5-sulfonamidoindole derivatives. Eur. J. Med. Chem. 1998, 33, 143–148. [Google Scholar] [CrossRef]
- Fraga, A. G. M.; Rodrigues, C. R.; Miranda, A. L. P.; Barreiro, E. J.; Fraga, C. A. M. Synthesis and Pharmacological evaluation of novel heterocyclic acylhydrazone derivatives, designed as PAF Antagonists. Eur. J. Pharm. Sci. 2000, 11, 285–290. [Google Scholar] [CrossRef]
- Walcourt, A.; Loyevsky, M.; Lovejoy, D. B.; Gordeuk, V. R.; Richardson, D. R. Novel aroylhydrazone and thiosemicarbazone iron chelators with anti-malarial activity against chloroquine-resistant and -sensitive parasites. Int. J. Biochem. Cell Biol. 2004, 36, 401–407. [Google Scholar] [CrossRef]
- Savini, L.; Chiasserini, L.; Travagli, V.; Pellerano, C.; Novellino, E.; Cosentino, S.; Pisano, M. B. New α-heterocyclic hydrazones: evaluation of anticancer, anti-HIV and antimicrobial activity. Eur. J. Med. Chem. 2004, 39, 113–122. [Google Scholar] [CrossRef] [PubMed]
- Mort, J.; Pfister, G. Electronic Properties of Polymers; Wiley: New York, 1982. [Google Scholar]
- Döbler, M.; Weder, C.; Neuenschwander, P.; Suter, U.W.; Follonier, S.; Bosshard, C.; Günter, P. Synthesis and Characterization of New Photorefractive Polymers with High Glass Transition Temperatures. Macromolecules 1998, 31, 6184–6189. [Google Scholar] [CrossRef]
- Nam, H.; Kang, D. H.; Kim, J. K.; Park, S. Y. Synthesis of Hole-Transporting Hydrazone Dendrimers. Chem. Lett. 2000, 11, 1298–1299. [Google Scholar] [CrossRef]
- Simokaitiene, J.; Danilevicius, A.; Grigalevicius, S.; Grazulevicius, J. V.; Getautis, V.; Jankauskas, V. Phenotiazinyl-based hydrazones as new hole-transporting materials for electrophotographic photoreceptors. Synthetic Metals 2006, 156, 926–931. [Google Scholar] [CrossRef]
- Naqvi, A.; Shahnawaaz, M.; Rao, A. V.; Seth, D. S.; Sharma, N. K. Synthesis of novel Hydrazino-3-oxo-N-(4-sulfamoylphenyl)-propanamide. Molbank 2009, M586. [Google Scholar] [CrossRef]
© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).