Abstract
8-Hydroxyquninoline Mannich base namely 7-diethylaminobenzyl-8-hydroxyqunioline(DEBQ) was synthesized and characterized by elemental analysis and spectral studies. Chelates of DEBQ with manganese(II) and nickel(II) were isolated and structurally characterized by elemental analysis, electrical conductance, magnetic susceptibility measurement, thermal analysis, IR,UV-Vis, EPR and Mass spectral data. The Mannich base ligand is bidentate and chelates through the phenolic oxygen and the aliphatic tertiary amino nitrogen atoms. Based on the magnetic and electronic spectral data all the MnII complexes are assigned an octahedral geometry and NiII complexes are assigned a tetrahedral geometry. Antimicrobial susceptibility screening of the Mannich base shows that it possesses excellent activity when compared to the standard drugs and the metal complexes studied. Among the chelates, MnII chelate is more potent than NiII chelate. Thermal analysis of a few compounds shows two stage decomposition patterns.
Highlights
IntroductionSynthetic chemists and pharmacologists show much interest in heterocyclic compounds containing quinoline moiety because of their unique chemical and pharmacological properties (Balasubramanium M and Keay, JG, 1996; Micheal IP, 1997; Maguire M P et al, 1994).Quinoline derivatives exhibit versatile pharmacological properties(Vetrivel Nadaraj et al, 2006; Pandey V.K and Menal Tondan, 2001; Yuki Sowda et al, 2004; Brain D Lee et al 2004; Singh O MV and Muthukrishnan M, 2001; Guytan A C and Hall JE, 1998; Rao A et al, 2002; Meth-Cohn et al, 1981) such as antiinflammatory, antibacterial, antifungal, antiallergic, antidepressant, antiasthmatic, antimalarial, antiviral, antitumour, neuroleptic, antihypertensive, cytotoxic, hypnotic, sedative,bronchodilator etc activities.8-Hydroxyquinoline is toxic if injected directly but its derivatives are useful as medicine in view of their biological activities . 8-Hydroxyquinoline is much useful in analytical chemistry due to its chelating ability(Bassett J et al, 2000).When 8-hydroxyquinoline is subjected to Mannich condensation with aldehydes and secondary amines it yields Mannich bases which could display more potent pharmacological properties and stronger chelating tendencies
Mannich base coordination chemistry has been a popular area of research due to the diverse range of biological, analytical and industrial applications of the Mannich base metal chelates (Sathya et al, 2012; Muthukumar C et al, 2012; Ramesh M and Sabastiyan A,2012, Sabastiyan A and Yosuva Suvaikin M,2012)
MnII and NiII chelates of 7-diethylaminobenzyl-8-hydroxyquinoline(DEBQ) have been synthesized, characterized and their antimicrobial potency screened against a few pathogenic microorganisms
Summary
Synthetic chemists and pharmacologists show much interest in heterocyclic compounds containing quinoline moiety because of their unique chemical and pharmacological properties (Balasubramanium M and Keay, JG, 1996; Micheal IP, 1997; Maguire M P et al, 1994).Quinoline derivatives exhibit versatile pharmacological properties(Vetrivel Nadaraj et al, 2006; Pandey V.K and Menal Tondan, 2001; Yuki Sowda et al, 2004; Brain D Lee et al 2004; Singh O MV and Muthukrishnan M, 2001; Guytan A C and Hall JE, 1998; Rao A et al, 2002; Meth-Cohn et al, 1981) such as antiinflammatory, antibacterial, antifungal, antiallergic, antidepressant, antiasthmatic, antimalarial, antiviral, antitumour, neuroleptic, antihypertensive, cytotoxic, hypnotic, sedative,bronchodilator etc activities.8-Hydroxyquinoline is toxic if injected directly but its derivatives are useful as medicine in view of their biological activities . 8-Hydroxyquinoline is much useful in analytical chemistry due to its chelating ability(Bassett J et al, 2000).When 8-hydroxyquinoline is subjected to Mannich condensation with aldehydes and secondary amines it yields Mannich bases which could display more potent pharmacological properties and stronger chelating tendencies. 8-Hydroxyquinoline is much useful in analytical chemistry due to its chelating ability(Bassett J et al, 2000).When 8-hydroxyquinoline is subjected to Mannich condensation with aldehydes and secondary amines it yields Mannich bases which could display more potent pharmacological properties and stronger chelating tendencies. Mannich base coordination chemistry has been a popular area of research due to the diverse range of biological, analytical and industrial applications of the Mannich base metal chelates (Sathya et al, 2012; Muthukumar C et al, 2012; Ramesh M and Sabastiyan A,2012, Sabastiyan A and Yosuva Suvaikin M,2012).
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