Planarity of benzoylthiocarbazate tuberculostatics. III. Diesters of 3-(2-hydroxybenzoyl)dithiocarbazic acid.
Searches for new tuberculostatic agents are important considering the occurrence of drug-resistant strains of Mycobacterium tuberculosis. The structures of three new potentially tuberculostatic compounds, namely isopropyl methyl (2-hydroxybenzoyl)carbonohydrazonodithioate, C12H16N2O2S2, (Z)-benzyl methyl (2-hydroxybenzoyl)carbonohydrazonodithioate, C16H16N2O2S2, and dibenzyl (2-hydroxybenzoyl)carbonohydrazonodithioate propan-2-ol monosolvate, C22H20N2O2S2·C3H8O, were determined by X-ray diffraction. The mutual orientation of the three main fragments of the compounds, namely an aromatic ring, a dithioester group and a hydrazide group, can influence the biological activity of the compounds. In all three of the structures studied, the C(=O)NH group is in the anti conformation. In addition, the presence of the hydroxy group in the ortho position of the aromatic ring in all three structures leads to the formation of an intramolecular hydrogen bond stabilizing the planarity of the molecules.
Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Poland.
Małgorzata
M
Szczesio
Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Poland.
Andrzej
A
Olczak
Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Poland.
Ida
I
Mazerant
Department of Organic Chemistry, Medical University of Gdańsk, Poland.
Katarzyna
K
Gobis
Department of Organic Chemistry, Medical University of Gdańsk, Poland.
Henryk
H
Foks
Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Poland.
Marek L
ML
Główka
DFT calculations; Mycobacterium tuberculosis; benzohydrazides; computational chemistry; crystal structure; tuberculostatic activity