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Synthesis, characterization, and tuberculostatic activity of novel 2-(4-nitrobenzoyl)hydrazinecarbodithioic acid derivatives.

Gobis K, Foks H, Augustynowicz-Kopec E, Napiorkowska A, Szczesio M, Olczak A, Glowka ML - Monatsh. Chem. (2012)

Bottom Line: Novel 5-(4-nitrophenyl)-1,3,4-oxadiazoles were also obtained.Promising preliminary results were obtained for some of the compounds.The crystal structure of the most active compound was determined.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdansk, 107 Gen. Hallera Str., 80-416 Gdansk, Poland.

ABSTRACT

Abstract: A series of novel S-esters of 2-(4-nitrobenzoyl)hydrazinecarbodithioic acid and S,S'-diesters of (4-nitrobenzoyl)carbonohydrazonodithioic acid were synthesized by reaction of 4-nitrobenzohydrazide and N-methyl-4-nitrobenzohydrazide with carbon disulfide and alkyl halides in the presence of triethylamine. Novel 5-(4-nitrophenyl)-1,3,4-oxadiazoles were also obtained. The structures were confirmed by IR, NMR, and mass spectroscopy, and by elemental analysis. All the compounds obtained were screened in vitro for their tuberculostatic activity. Promising preliminary results were obtained for some of the compounds. The crystal structure of the most active compound was determined.

No MeSH data available.


 
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Mentions: The synthetic route of the target compounds is outlined in Schemes 1 and 2. First, symmetrical S,S′-diesters of 4-nitrobenzoylocarbonohydrazonodithioic acid and N-methyl-4-nitrobenzoylcarbonohydrazonodithioic acid (1–9) were synthesized. Modification within the thioxyl group gave methyl, isopropyl, n-butyl, n-decyl, and benzyl S,S′-diesters. Substituents were chosen to differ substantially in size. Esters of 1,3-dithiolane and 1,3-dithiane with cyclic structures were also obtained (11–14, Scheme 1).Scheme 1


Synthesis, characterization, and tuberculostatic activity of novel 2-(4-nitrobenzoyl)hydrazinecarbodithioic acid derivatives.

Gobis K, Foks H, Augustynowicz-Kopec E, Napiorkowska A, Szczesio M, Olczak A, Glowka ML - Monatsh. Chem. (2012)

 
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4494774&req=5

Sch2:  
Mentions: The synthetic route of the target compounds is outlined in Schemes 1 and 2. First, symmetrical S,S′-diesters of 4-nitrobenzoylocarbonohydrazonodithioic acid and N-methyl-4-nitrobenzoylcarbonohydrazonodithioic acid (1–9) were synthesized. Modification within the thioxyl group gave methyl, isopropyl, n-butyl, n-decyl, and benzyl S,S′-diesters. Substituents were chosen to differ substantially in size. Esters of 1,3-dithiolane and 1,3-dithiane with cyclic structures were also obtained (11–14, Scheme 1).Scheme 1

Bottom Line: Novel 5-(4-nitrophenyl)-1,3,4-oxadiazoles were also obtained.Promising preliminary results were obtained for some of the compounds.The crystal structure of the most active compound was determined.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdansk, 107 Gen. Hallera Str., 80-416 Gdansk, Poland.

ABSTRACT

Abstract: A series of novel S-esters of 2-(4-nitrobenzoyl)hydrazinecarbodithioic acid and S,S'-diesters of (4-nitrobenzoyl)carbonohydrazonodithioic acid were synthesized by reaction of 4-nitrobenzohydrazide and N-methyl-4-nitrobenzohydrazide with carbon disulfide and alkyl halides in the presence of triethylamine. Novel 5-(4-nitrophenyl)-1,3,4-oxadiazoles were also obtained. The structures were confirmed by IR, NMR, and mass spectroscopy, and by elemental analysis. All the compounds obtained were screened in vitro for their tuberculostatic activity. Promising preliminary results were obtained for some of the compounds. The crystal structure of the most active compound was determined.

No MeSH data available.