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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.


Structures of dimethyl 2-nitrobenzoylcarbonohydrazonodithioate (a) and dimethyl 4-nitrobenzoylcarbonohydrazonodithioate (b)
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Fig2: Structures of dimethyl 2-nitrobenzoylcarbonohydrazonodithioate (a) and dimethyl 4-nitrobenzoylcarbonohydrazonodithioate (b)

Mentions: Our previous studies on the synthesis of new compounds with antituberculous activity helped formulate the hypothesis of the relationship between the tuberculostatic activity of compounds in the isoniazid analog group and the coplanar structure of their molecules. Among others S-methyl and S,S′-dimethyl amino(pyridin-2-ylmethylene)carbonohydrazonodithioates have been synthesized. These compounds had high tuberculostatic activity in vitro, with MIC (minimum concentrations inhibiting the growth of mycobacteria) of 3.13 μg/cm3 [12, 13]. Crystallographic studies performed on these derivatives indicated their molecules have a planar structure. The adoption of such a structure is a result of intramolecular hydrogen bond formation (Fig. 1). This condition is also met by the S-esters and S,S′-diesters of benzoylhydrazinecarbodithioic acids derived from benzohydrazides, especially those that have the appropriate substituents at C-2 position of the benzene ring. For some of the compounds in this group high tuberculostatic activity in vitro has been detected [14]. Unexpectedly, we found no correlation between the almost planar structure of a derivative with an NO2 group in C-2 position and its activity towards Mycobacterium tuberculosis. The structure of the most active compound with an NO2 group in C-4 position has no ability to form a hydrogen bond and adopt a planar structure (Fig. 2). That compound was the most active against H37Rv standard strain and sensitive 192 strain (MICs 3.1 μg/cm3). Its activity against resistant 210 strain was lower (MIC 25 μg/cm3).Fig. 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)

Structures of dimethyl 2-nitrobenzoylcarbonohydrazonodithioate (a) and dimethyl 4-nitrobenzoylcarbonohydrazonodithioate (b)
© Copyright Policy
Related In: Results  -  Collection

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

Fig2: Structures of dimethyl 2-nitrobenzoylcarbonohydrazonodithioate (a) and dimethyl 4-nitrobenzoylcarbonohydrazonodithioate (b)
Mentions: Our previous studies on the synthesis of new compounds with antituberculous activity helped formulate the hypothesis of the relationship between the tuberculostatic activity of compounds in the isoniazid analog group and the coplanar structure of their molecules. Among others S-methyl and S,S′-dimethyl amino(pyridin-2-ylmethylene)carbonohydrazonodithioates have been synthesized. These compounds had high tuberculostatic activity in vitro, with MIC (minimum concentrations inhibiting the growth of mycobacteria) of 3.13 μg/cm3 [12, 13]. Crystallographic studies performed on these derivatives indicated their molecules have a planar structure. The adoption of such a structure is a result of intramolecular hydrogen bond formation (Fig. 1). This condition is also met by the S-esters and S,S′-diesters of benzoylhydrazinecarbodithioic acids derived from benzohydrazides, especially those that have the appropriate substituents at C-2 position of the benzene ring. For some of the compounds in this group high tuberculostatic activity in vitro has been detected [14]. Unexpectedly, we found no correlation between the almost planar structure of a derivative with an NO2 group in C-2 position and its activity towards Mycobacterium tuberculosis. The structure of the most active compound with an NO2 group in C-4 position has no ability to form a hydrogen bond and adopt a planar structure (Fig. 2). That compound was the most active against H37Rv standard strain and sensitive 192 strain (MICs 3.1 μg/cm3). Its activity against resistant 210 strain was lower (MIC 25 μg/cm3).Fig. 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.