Synthesis and Evaluation of the Antibacterial and Antitubercular Activity of Some N1-Aral-N4-(3-Chloro-4-fluorophenyl) thiosemicarbazones and their Copper(I) Complexes

Abstract

New N1-aral-N4- (3-chloro-4-fluorophenyl)thiosemicarbazones (2a-h) and their Cu(I) complexes (3a-h) have been prepared and characterized by elemental analysis and spectral methods (IR and 1H-NMR). Thiosemicarbazones 2a-h bind to copper(I) as bidentate ligand via nitrogen and thione sulphur centers to afford 3a-h. Both ligands and their complexes are screened against Escherichia coli (National Collection of Type Culture 10418) and Staphylococcus aureus (National Collection of Type Culture 5571) to evaluate their antibacterial properties and against human virulent H37Rv strain of Mycobacterium tuberculosis for their antitubercular properties. Ligands 2d-h showed promising antibacterial activity while their Cu(I) complexes 3d-h exhibited excellent activity. The compounds 2a, 2d, 2f, 2g and their Cu(I) complexes 3a, 3d, 3f and 3g were evaluated for their antitubercular activity. It was observed that compounds 2a, 2g, 3a, 3d showed moderate activity while 3f and 3g exhibited promising antitubercular activity.

Synthesis and Structural Characterization of Fluorinated Thiosemicarbazones

“…We have been interested in fluorinated compounds for a long time [12] since inclusion of fluorine atoms in molecules often has a marked effect on their physical and chemical properties. For example, although it has been recognized that fluorine-containing drugs are often far more therapeutically active than their non-fluorinated analogs [13] it is surprising that relatively very little is known about the properties of fluorine-containing thiosemicarbazones [14,15]. In this paper, we report the syntheses of six new polyfluorobenzaldehyde thiosemicarbazones: RC(R′)=N-NH-C(S)NH 2 (R = 2,4-C 6 H 3 F 2 , R′ = H ( 1) ; R = 2,5-C 6 H 3 F 2 , R′ = H ( 2 ); R = 2,6-C 6 H 3 F 2 , R′ = H ( 3 ); R = 3,4-C 6 H 3 F 2 , R′ = H ( 4 ); R = 3,5-C 6 H 3 F 2 , R′ = H ( 5 ) and R = 4-C 6 H 4 F, R′ = C 6 H 5 , ( 6 )) and their corresponding X-ray diffraction structures.…”

Quantum Chemical Studies on Some Thiosemicarbazone Derivatives as Ribonucleotide Reductase Inhibitor

“…The studied molecules and their activity has been given in Table 1 [33,34], andclassified into seven groups for further comparisons and discussion. These groups were: The degree of activity of the molecules could be differentiated through groups; each group have its own activity; related to its composition; for example, when R is hydroxy group (OH) in the position 4, the molecules were active as in the molecules (3,4,(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21), but when the hydroxy group was in position 2, the molecules were inactive as in the compounds (1 and 2). Additionally, the presence of other group like methoxy group (OCH 3 ), or hydroxyl group (OH) in the position 4 as in the molecules (5 and 6), that were inactive, a similar kind of positional activity for molecule (7 and 8) and (9 and 10), contains furyl and thiophenyl respectively, the R1 group type and its position indicates the amount of activity.…”

“…In addition to the antitumor effect of transition metal complexes of thiosemicarbazones [7][8][9], it is well known that the compounds have antiviral as well asanti-HIV properties [8,[10][11][12][13]. Numerous thiosemicarbazones, especially their Cu (II) [14] complexes, have been studied substantially for their antibacterial and antifungal properties [15][16][17]. Furthermore, it is worthwhile to mentioned that the thiosemicarbazones have anticonvulsant [18], anti-malarial [13], antiamoebic [19,20] and antioxidant properties [21] with other biological activities.…”

cis-Dioxomolybdenum(VI) complexes of a new ONN chelating thiosemicarbazidato ligand; Synthesis, characterization, crystal, molecular structures and antioxidant activities

“…Thiosemicarbazones and their metal complexes have raised considerable interest in pharmacology due to their wide range of biological activities such as antitumor [1][2][3][4], antiviral [5][6][7], antifungal [8][9][10], antioxidant [11] and DNA-binding properties [12][13][14]. Molybdenum is an oligo-element and one of the cofactors for several enzymes catalyzing redox reactions [15].…”