Reaction of Some Substituted 3-Aryl-4-formylsydnones with Tetra-Oacetyl- β-D-galactopyranosyl)thiosemicarbazide

Author(s): Nguyen Dinh Thanh, Hoang Thanh Duc, Nguyen Hoang Minh Hue, Hoang Thi Kim Van.

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 8 , 2016

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Graphical Abstract:


Background: Thiosemicarbazones containing mono- or disaccharide moieties reveal several various remarkable biological activities; therefore these compounds have been focused in organic syntheses. Sydnone ring is the potential basic pharmacodynamic nucleus, which has been reported to possess a wide variety of biological activities such as antitumor, anticancer, anti-inflammatory, antiviral, and scavenging activities. The connection of monosaccharide moiety to sydnone ring could initiate the new activities.

Methods: The synthetic reaction of different substituted 3-phenyl-4-formylsydnone N-(tetra-O-acetyl-β- D-galactopyranosyl)thiosemicarbazones was carried out under microwave-assisted heating conditions. The structures of obtained thiosemicarbazones were confirmed by IR, NMR and mass spectra. All obtained thiosemicarbazones were screened for DPPH radical scavenging ability.

Results: Some different substituted 3-formyl-4-phenylsydnones were prepared by Vilsmeier-Haackʹs formylation reaction. These substituted 4-formylsydnones were converted into corresponding thiosemicarbazones by condensation with N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thiosemicarbazide. Some of these thiosemicarbazones showed remarkable DPPH radical scavenging ability.

Conclusion: The efficient synthesis of 3-phenyl-4-formylsydnone N-(tetra-O-acetyl-β-D-galactopyranosyl) thiosemicarbazones under microwave-assisted refluxing conditions has been reported. Reaction yields were 40-80%. Obtained results showed that the compounds 4f and 4g have high antioxidant activity.

Keywords: D-Galactose, DPPH radical, 4-Formylsydnone, thiosemicarbazide, microwave-assisted.

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Article Details

Year: 2016
Page: [541 - 546]
Pages: 6
DOI: 10.2174/1570178613666160824104037
Price: $65

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