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Synthesis, characterization and biological activities of 3-methylbenzyl 2-(6-methyl pyridin-2-ylmethylene)hydrazine carbodithioate and its transition metal complexes

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Abstract

A tridentate nitrogen-sulfur Schiff base, 3-methylbenzyl 2-(6-methylpyridin-2-ylmethylene)hydrazine carbodithioate (6mpyS3M), was synthesized by condensation of 6-methylpyridine-2-aldehyde with S-3-methylbenzyldithiocarbazate. It crystallized in space group P 21/n. It displayed intermolecular N–H···N hydrogen bonding between the α-nitrogen and the pyridyl nitrogen. The thione sulfur is in a trans position with respect to the 6-methylpyridine fragment across the C–N bond but adopts a cis position with the 3-methylbenzyl fragment through the C–S bond. Octahedral complexes containing two 6mpyS3M ligands were prepared with Cu(II), Ni(II), Zn(II) and Cd(II). 6mpyS3M and its metal complexes were assayed against selected microbes and two breast cancer cell lines. 6mpyS3M was strongly active against both cancer cell lines. Its metal complexes showed high selectivity with Cu(II), Ni(II) and Zn(II) complexes strongly active against only one of the cancer cell lines, whereas the Cd(II) complex was strongly active only against the other. Only Cu(II) and Cd(II) complexes were active against some of the bacteria.

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Acknowledgments

We thank the Department of Chemistry, the Laboratory of Molecular and Cell Biology, Institute of Biosciences and the Molecular Genetics Laboratory, Department of Obstetrics and Gynaecology, Universiti Putra Malaysia, for the provision of laboratory facilities and the Chemical Crystallography Lab, Oxford University for providing X-ray crystallographic services. The research was funded by a grant from the Ministry of Science and Environment, Malaysia, under the Intensification of Research in Priority Areas Scheme (IRPA grant No. 09-02-04-0296) F.N.F.H. wishes to thank the Malaysian Government for a National Science Fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    Thahira B. S. A. Ravoof, Karen A. Crouse, M. Ibrahim M. Tahir & Fiona N. F. How

  2. Department of Obstetrics and Gynaecology, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    Rozita Rosli

  3. Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, OX1 3TA, Oxford, UK

    David J. Watkins

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  1. Thahira B. S. A. Ravoof
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  2. Karen A. Crouse
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  3. M. Ibrahim M. Tahir
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  4. Fiona N. F. How
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  5. Rozita Rosli
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Correspondence to Thahira B. S. A. Ravoof.

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** CCDC Code 705352.

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Ravoof, T.B.S.A., Crouse, K.A., Tahir, M.I.M. et al. Synthesis, characterization and biological activities of 3-methylbenzyl 2-(6-methyl pyridin-2-ylmethylene)hydrazine carbodithioate and its transition metal complexes. Transition Met Chem 35, 871–876 (2010). https://doi.org/10.1007/s11243-010-9406-6

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  • DOI: https://doi.org/10.1007/s11243-010-9406-6

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