Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde

A substituted dithiocarbazate moiety has been prepared using 4-picolylchloride hydrochloride to obtain S-4-picolyldithiocarbazate (S4PDTC) and its by-product (S4diPDTC). Two Schiff bases were synthesized by reacting S-4-picolyldithiocarbazate with pyridine-2-carboxaldehyde (Pc4PDTC) and 4-carboxyben...

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Main Authors: Khoo, Teng Jin, Break, Mohammed Khaled, Crouse, Karen Anne, Mohamed Tahir, Mohamed Ibrahim, Ali, A. M., Cowley, Andrew R., Watkin, D. J., Tarafder, M. T. H.
Format: Article
Published: Elsevier 2014
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author Khoo, Teng Jin
Break, Mohammed Khaled
Crouse, Karen Anne
Mohamed Tahir, Mohamed Ibrahim
Ali, A. M.
Cowley, Andrew R.
Watkin, D. J.
Tarafder, M. T. H.
author_facet Khoo, Teng Jin
Break, Mohammed Khaled
Crouse, Karen Anne
Mohamed Tahir, Mohamed Ibrahim
Ali, A. M.
Cowley, Andrew R.
Watkin, D. J.
Tarafder, M. T. H.
author_sort Khoo, Teng Jin
collection UPM
description A substituted dithiocarbazate moiety has been prepared using 4-picolylchloride hydrochloride to obtain S-4-picolyldithiocarbazate (S4PDTC) and its by-product (S4diPDTC). Two Schiff bases were synthesized by reacting S-4-picolyldithiocarbazate with pyridine-2-carboxaldehyde (Pc4PDTC) and 4-carboxybenzaldehyde (Cb4PDTC). Ni(II), Cu(II), Zn(II) and Cd(II) complexes of the Schiff bases were characterized by various physico-chemical and spectroscopic methods viz. CHNS elemental analyses, molar conductivity, IR, UV–Vis, 1H and 13C NMR, mass spectrometry and magnetic susceptibility. X-ray crystallographic analysis has been carried out on the by-product and the Cd complex of the ligand derived from (Pc4PDTC). The ligands and their metal complexes were assayed in vitro for cytotoxic, antimicrobial and antioxidant activities. The Pc4PDTC Schiff base showed moderate cytotoxicity against human promyolicytic leukemic (HL60) cell line with a CD50 value of 9 μg/cm3 while Cb4PDTC was inactive. Complexing Pc4PDTC with cadmium(II) and copper(II) enhanced its cytotoxicity against the human promyolicytic leukemic cell line (HL60) from moderately to highly active. S4PDTC showed marked antimicrobial activity against bacteria but was inactive towards fungi. Copper(II) and cadmium(II) complexes of the two Schiff bases showed clear inhibition zones for most of the fungi and bacteria tested. Antioxidant properties of Pc4PDTC and Cb4PDTC Schiff bases were comparable to the commercially available buthylatedhydroxytoluene (BHT).
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spelling upm.eprints-355822016-01-18T01:23:58Z http://psasir.upm.edu.my/id/eprint/35582/ Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde Khoo, Teng Jin Break, Mohammed Khaled Crouse, Karen Anne Mohamed Tahir, Mohamed Ibrahim Ali, A. M. Cowley, Andrew R. Watkin, D. J. Tarafder, M. T. H. A substituted dithiocarbazate moiety has been prepared using 4-picolylchloride hydrochloride to obtain S-4-picolyldithiocarbazate (S4PDTC) and its by-product (S4diPDTC). Two Schiff bases were synthesized by reacting S-4-picolyldithiocarbazate with pyridine-2-carboxaldehyde (Pc4PDTC) and 4-carboxybenzaldehyde (Cb4PDTC). Ni(II), Cu(II), Zn(II) and Cd(II) complexes of the Schiff bases were characterized by various physico-chemical and spectroscopic methods viz. CHNS elemental analyses, molar conductivity, IR, UV–Vis, 1H and 13C NMR, mass spectrometry and magnetic susceptibility. X-ray crystallographic analysis has been carried out on the by-product and the Cd complex of the ligand derived from (Pc4PDTC). The ligands and their metal complexes were assayed in vitro for cytotoxic, antimicrobial and antioxidant activities. The Pc4PDTC Schiff base showed moderate cytotoxicity against human promyolicytic leukemic (HL60) cell line with a CD50 value of 9 μg/cm3 while Cb4PDTC was inactive. Complexing Pc4PDTC with cadmium(II) and copper(II) enhanced its cytotoxicity against the human promyolicytic leukemic cell line (HL60) from moderately to highly active. S4PDTC showed marked antimicrobial activity against bacteria but was inactive towards fungi. Copper(II) and cadmium(II) complexes of the two Schiff bases showed clear inhibition zones for most of the fungi and bacteria tested. Antioxidant properties of Pc4PDTC and Cb4PDTC Schiff bases were comparable to the commercially available buthylatedhydroxytoluene (BHT). Elsevier 2014-03-24 Article PeerReviewed Khoo, Teng Jin and Break, Mohammed Khaled and Crouse, Karen Anne and Mohamed Tahir, Mohamed Ibrahim and Ali, A. M. and Cowley, Andrew R. and Watkin, D. J. and Tarafder, M. T. H. (2014) Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde. Inorganica Chimica Acta, 413. pp. 68-76. ISSN 0020-1693 http://www.sciencedirect.com/science/article/pii/S0020169314000115 10.1016/j.ica.2014.01.001
spellingShingle Khoo, Teng Jin
Break, Mohammed Khaled
Crouse, Karen Anne
Mohamed Tahir, Mohamed Ibrahim
Ali, A. M.
Cowley, Andrew R.
Watkin, D. J.
Tarafder, M. T. H.
Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde
title Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde
title_full Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde
title_fullStr Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde
title_full_unstemmed Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde
title_short Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde
title_sort synthesis characterization and biological activity of two schiff base ligands and their nickel ii copper ii zinc ii and cadmium ii complexes derived from s 4 picolyldithiocarbazate and x ray crystal structure of cadmium ii complex derived from pyridine 2 carboxaldehyde
work_keys_str_mv AT khootengjin synthesischaracterizationandbiologicalactivityoftwoschiffbaseligandsandtheirnickeliicopperiizinciiandcadmiumiicomplexesderivedfroms4picolyldithiocarbazateandxraycrystalstructureofcadmiumiicomplexderivedfrompyridine2carboxaldehyde
AT breakmohammedkhaled synthesischaracterizationandbiologicalactivityoftwoschiffbaseligandsandtheirnickeliicopperiizinciiandcadmiumiicomplexesderivedfroms4picolyldithiocarbazateandxraycrystalstructureofcadmiumiicomplexderivedfrompyridine2carboxaldehyde
AT crousekarenanne synthesischaracterizationandbiologicalactivityoftwoschiffbaseligandsandtheirnickeliicopperiizinciiandcadmiumiicomplexesderivedfroms4picolyldithiocarbazateandxraycrystalstructureofcadmiumiicomplexderivedfrompyridine2carboxaldehyde
AT mohamedtahirmohamedibrahim synthesischaracterizationandbiologicalactivityoftwoschiffbaseligandsandtheirnickeliicopperiizinciiandcadmiumiicomplexesderivedfroms4picolyldithiocarbazateandxraycrystalstructureofcadmiumiicomplexderivedfrompyridine2carboxaldehyde
AT aliam synthesischaracterizationandbiologicalactivityoftwoschiffbaseligandsandtheirnickeliicopperiizinciiandcadmiumiicomplexesderivedfroms4picolyldithiocarbazateandxraycrystalstructureofcadmiumiicomplexderivedfrompyridine2carboxaldehyde
AT cowleyandrewr synthesischaracterizationandbiologicalactivityoftwoschiffbaseligandsandtheirnickeliicopperiizinciiandcadmiumiicomplexesderivedfroms4picolyldithiocarbazateandxraycrystalstructureofcadmiumiicomplexderivedfrompyridine2carboxaldehyde
AT watkindj synthesischaracterizationandbiologicalactivityoftwoschiffbaseligandsandtheirnickeliicopperiizinciiandcadmiumiicomplexesderivedfroms4picolyldithiocarbazateandxraycrystalstructureofcadmiumiicomplexderivedfrompyridine2carboxaldehyde
AT tarafdermth synthesischaracterizationandbiologicalactivityoftwoschiffbaseligandsandtheirnickeliicopperiizinciiandcadmiumiicomplexesderivedfroms4picolyldithiocarbazateandxraycrystalstructureofcadmiumiicomplexderivedfrompyridine2carboxaldehyde