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Synthesis, structure, and tuberculostatic activity of dimethyl benzoylcarbonohydrazonodithioates.

Gobis K, Foks H, Zwolska Z, Augustynowicz-Kopeć E, Główka ML, Olczak A, Sabisz M - Monatsh. Chem. (2011)

Bottom Line: New dimethyl benzoylcarbonohydrazonodithioates were obtained by CS2 addition to arylcarboxylic acid hydrazides and methylation of the formed adduct.The new derivatives were tested for their activity against Mycobacterium tuberculosis.Some compounds exhibited high activity toward sensitive and resistant strains.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdansk, Gdansk, Poland.

ABSTRACT

Abstract: New dimethyl benzoylcarbonohydrazonodithioates were obtained by CS2 addition to arylcarboxylic acid hydrazides and methylation of the formed adduct. The new derivatives were tested for their activity against Mycobacterium tuberculosis. Some compounds exhibited high activity toward sensitive and resistant strains.

No MeSH data available.


Related in: MedlinePlus

ORTEP views of molecules 6 and 7 in their crystals. The ellipsoids are drawn at 50% probability level [16]. Crystal data: monoclinic, P21/c, Z = 4; with a = 8.138(1), b = 18.920(1), c = 9.270(1) Å, β = 111.77(1)°, R1 = 0.053 (wR2 = 0.177) for 2,044 observed reflections for 6; and a = 7.437(1), b = 23.140(1), c = 8.874(1) Å, β = 121.36(1)°, R1 = 0.043 (wR2 = 0.112) for 2,374 observed reflections for 7. The distances C1–N2 and N2–N3 are 1.272(3) and 1.390(3) Å for 6, and 1.276(3) and 1.401(2) Å and 7, indicating double bond character of the former bond. The dihedral angle between the phenyl ring and the carbonyl group is 58.0° for 6 and 33.6° for 7
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Fig1: ORTEP views of molecules 6 and 7 in their crystals. The ellipsoids are drawn at 50% probability level [16]. Crystal data: monoclinic, P21/c, Z = 4; with a = 8.138(1), b = 18.920(1), c = 9.270(1) Å, β = 111.77(1)°, R1 = 0.053 (wR2 = 0.177) for 2,044 observed reflections for 6; and a = 7.437(1), b = 23.140(1), c = 8.874(1) Å, β = 121.36(1)°, R1 = 0.043 (wR2 = 0.112) for 2,374 observed reflections for 7. The distances C1–N2 and N2–N3 are 1.272(3) and 1.390(3) Å for 6, and 1.276(3) and 1.401(2) Å and 7, indicating double bond character of the former bond. The dihedral angle between the phenyl ring and the carbonyl group is 58.0° for 6 and 33.6° for 7

Mentions: Reactions were performed in ethanol–water solution at room temperature and occurred with good yields. The structures of the obtained compounds were confirmed by elemental analysis, IR, 1H and 13C NMR spectroscopy, and mass spectrometry (compounds 1 and 2); compounds 6 and 7 were also unequivocally determined by X-ray diffraction (Fig. 1).Fig. 1


Synthesis, structure, and tuberculostatic activity of dimethyl benzoylcarbonohydrazonodithioates.

Gobis K, Foks H, Zwolska Z, Augustynowicz-Kopeć E, Główka ML, Olczak A, Sabisz M - Monatsh. Chem. (2011)

ORTEP views of molecules 6 and 7 in their crystals. The ellipsoids are drawn at 50% probability level [16]. Crystal data: monoclinic, P21/c, Z = 4; with a = 8.138(1), b = 18.920(1), c = 9.270(1) Å, β = 111.77(1)°, R1 = 0.053 (wR2 = 0.177) for 2,044 observed reflections for 6; and a = 7.437(1), b = 23.140(1), c = 8.874(1) Å, β = 121.36(1)°, R1 = 0.043 (wR2 = 0.112) for 2,374 observed reflections for 7. The distances C1–N2 and N2–N3 are 1.272(3) and 1.390(3) Å for 6, and 1.276(3) and 1.401(2) Å and 7, indicating double bond character of the former bond. The dihedral angle between the phenyl ring and the carbonyl group is 58.0° for 6 and 33.6° for 7
© Copyright Policy
Related In: Results  -  Collection

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getmorefigures.php?uid=PMC4494766&req=5

Fig1: ORTEP views of molecules 6 and 7 in their crystals. The ellipsoids are drawn at 50% probability level [16]. Crystal data: monoclinic, P21/c, Z = 4; with a = 8.138(1), b = 18.920(1), c = 9.270(1) Å, β = 111.77(1)°, R1 = 0.053 (wR2 = 0.177) for 2,044 observed reflections for 6; and a = 7.437(1), b = 23.140(1), c = 8.874(1) Å, β = 121.36(1)°, R1 = 0.043 (wR2 = 0.112) for 2,374 observed reflections for 7. The distances C1–N2 and N2–N3 are 1.272(3) and 1.390(3) Å for 6, and 1.276(3) and 1.401(2) Å and 7, indicating double bond character of the former bond. The dihedral angle between the phenyl ring and the carbonyl group is 58.0° for 6 and 33.6° for 7
Mentions: Reactions were performed in ethanol–water solution at room temperature and occurred with good yields. The structures of the obtained compounds were confirmed by elemental analysis, IR, 1H and 13C NMR spectroscopy, and mass spectrometry (compounds 1 and 2); compounds 6 and 7 were also unequivocally determined by X-ray diffraction (Fig. 1).Fig. 1

Bottom Line: New dimethyl benzoylcarbonohydrazonodithioates were obtained by CS2 addition to arylcarboxylic acid hydrazides and methylation of the formed adduct.The new derivatives were tested for their activity against Mycobacterium tuberculosis.Some compounds exhibited high activity toward sensitive and resistant strains.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdansk, Gdansk, Poland.

ABSTRACT

Abstract: New dimethyl benzoylcarbonohydrazonodithioates were obtained by CS2 addition to arylcarboxylic acid hydrazides and methylation of the formed adduct. The new derivatives were tested for their activity against Mycobacterium tuberculosis. Some compounds exhibited high activity toward sensitive and resistant strains.

No MeSH data available.


Related in: MedlinePlus