Synthesis, Characterization, and Biological Activity ofN1-Methyl-2-(1H-1,2,3-Benzotriazol-1-y1)-3-Oxobutan-ethioamide Complexes with Some Divalent Metal (II) Ions

Abstract

A new series of Zn2+, Cu2+, Ni2+, and Co2+ complexes of N1-methyl-2-(1H-1,2,3-benzotriazol-1-yl)-3-oxobutanethioamide (MBOBT), HL, has been synthesized and characterized by different spectral and magnetic measurements and elemental analysis. IR spectral data indicates that (MBOBT) exists only in the thione form in the solid state while 13C NMR spectrum indicates its existence in thione and thiole tautomeric forms. The IR spectra of all complexes indicate that (MBOBT) acts as a monobasic bidentate ligand coordinating to the metal(II) ions via the keto-oxygen and thiolato-sulphur atoms. The electronic spectral studies showed that (MBOBT) bonded to all metal ions through sulphur and nitrogen atoms based on the positions and intensity of their charge transfer bands. Furthermore, the spectra reflect four coordinate tetrahedral zinc(II), tetragonally distorted copper(II), square planar nickel(II), and cobalt(II) complexes. Thermal decomposition study of the complexes was monitored by TG and DTG analyses under N2 atmosphere. The decomposition course and steps were analyzed and the activation parameters of the nonisothermal decomposition are determined. The isolated metal chelates have been screened for their antimicrobial activities and the findings have been reported and discussed in relation to their structures.

(E)-4-(Benzyloxy)benzaldehyde thiosemicarbazone

“…Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 ; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 The chemistry of thiosemicarbazones have been of immense interest because these compounds provide intriguing chelating patterns, profound biomedical properties, structural diversity and ion-sensing abilities (Al-Awadi et al, 2008;Amoedo et al, 2006;Demertzi et al, 2007;Mirsha et al, 2006;Kizilcikli et al, 2004). Compounds of this type have been used as antibacterial, antifungal and antitumor agents (Sing et al, 2001;Offiong et al, 1997).…”

“…For related structures of thiosemicarbazones, see, for example: John et al (2003); Joseph et al (2004). For applications and bioactivities of thiosemicarbazones, see, for example: Al-Awadi et al (2008); Amoedo et al (2006); Chandra et al, (2001); Demertzi et al (2007); Kizilcikli et al (2004); Mirsha et al (2006); Offiong & Martelli (1997); Sing et al (2001). Hydrogen-bond geometry (Å , ).…”

3-Hydroxy-4-methoxybenzaldehyde thiosemicarbazone hemihydrate

“…For details of hydrogen-bond motifs, see: Bernstein et al (1995). For background to thiosemicarbazones, see: Al-Awadi et al (2008); Kizilcikli et al (2004); Mishra et al (2006). For a related structure, see: Ferrari et al (2001).…”

“…Intriguing chelating patterns, biomedical properties, structural diversity and ion-sensing abilities (Al-Awadi et al, 2008;Kizilcikli et al, 2004;Mishra et al, 2006) have made thiosemicarbazones a class of compounds of immense importance.…”

Synthesis, Structural Characterization, and Biological Application of p-[N,N-bis(2-chloroethyl) Aminobenzaldehyde Thiosemicarbazone and Its Nickel (II) Complex

“…[1][2][3][4][5] Though the versatility of thiosemicarbazone ligands for binding and deprive cells of essential metal ions has been well established, this can be valid for tridentate (NNS donor, must to act as chemotherapeutic agents) ligands, with their high formation constants, but it is in striking contrast with the fact that the metal complexes are systematically more active than the ligands by themselves. Recently, the structural and biological activity of substituted thiosemicarbazone derived from p-fluorobenzaldehyde, [6] salicylaldehyde, [7][8][9] 2-hydroxy-1-naphthaldehyde, [10] thiophene-2,3-dicarboxaldehyde, [11] and p-[N,N-bis(2-chloroethyl)amino]benzaldehyde [12,13] also supports the synergic activity of the complex against various biological samples than the corresponding free thiosemicarbazone.…”