Synthesis and Antibacterial Activities of Sugar-containing Platinum Ethynyl Complexes

Authors

  • Ratan Kumar Paul Department of Chemistry, Pabna University of Science and Technology, Pabna-6600
  • Md Faruak Ahmad Department of Chemistry, Shahjalal University of Science and Technology, Sylhet-3114
  • Mohammad Mizanur Rahman Khan Department of Chemistry, Shahjalal University of Science and Technology, Sylhet-3114
  • Muhammad Younus Department of Chemistry, Shahjalal University of Science and Technology, Sylhet-3114

DOI:

https://doi.org/10.3329/jbas.v40i1.28326

Keywords:

Sonogashira coupling, Dehydrohalogenation, Sugar-containing platinum acetylide, Antibacterial activity

Abstract

New sugar-containing aryl ethynyl ligand [N-(4-trimethylsilylethynylphenyl)-?-D-glucopyranosylamine] 2 has been prepared by the reaction of [N-(4-iodophenyl)-?-D-glucopyranosylamine] 1 with trimethysilylacetylene in the presence of Pd(OAc)2/CuI catalyst, in iPr2NH and DMF solvent mixture. The trimethylsilyl group of compound 2 was deprotected using K2CO3 in methanol to form terminal ethynylene ligand [N-(?-D-glucopyranosyl)aniline-4-ethyne] 3. Novel platinum mono-ethynyl complex trans-[(P(Bu)3)2PtCl(C?C-4-C6H4-NH-D-glocose)] 4 and bis-ethynyl complex trans-[(P(Bu)3)2PtCl(C?C-4-C6H4-NH-D-glocose)2] 5 were formed by the dehydrohalogenation reaction of trans-[Pt(P(Bu)3)2Cl2] with terminal ethynyl ligand 3 in iPr2NH/THF, in the presence of CuI, at 65ºC. The complexes are hygroscopic in air, and are fairly soluble in methanol and CH2Cl2. The new compound 2 - 5 were characterized by FTIR and UV-Vis spectroscopy and elemental analysis. The compounds were tested for antibacterial activity using disk diffusion technique. The platinum complexes 4 and 5 displayed good resistivity against the following bacteria: Escherichia coli, Proteus penneri, Klebsiella oxytoca and Pseudomonas aeruginosa.

Journal of Bangladesh Academy of Sciences, Vol. 40, No. 1, 65-77, 2016

New sugar-containing aryl ethynyl ligand [N-(4-trimethylsilylethynylphenyl)-?-D-glucopyranosylamine] 2 has been prepared by the reaction of [N-(4-iodophenyl)-?-D-glucopyranosylamine] 1 with trimethysilylacetylene in the presence of Pd(OAc)2/CuI catalyst, in iPr2NH and DMF solvent mixture. The trimethylsilyl group of compound 2 was deprotected using K2CO3in methanol to form terminal ethynylene ligand [N-(?-D-glucopyranosyl)aniline-4-ethyne] 3. Novel platinum mono-ethynyl complex trans-[(P(Bu)3)2PtCl(C?C-4-C6H4-NH-D-glocose)] 4 and bis-ethynyl complex trans-[(P(Bu)3)2PtCl(C?C-4-C6H4-NH-D-glocose)2] 5 were formed by the dehydrohalogenation reaction of trans-[Pt(P(Bu)3)2Cl2] with terminal ethynyl ligand 3 in iPr2NH/THF, in the presence of CuI, at 65ºC. The complexes are hygroscopic in air, and are fairly soluble in methanol and CH2Cl2. The new compound 2 - 5 were characterized by FTIR and UV-Vis spectroscopy and elemental analysis. The compounds were tested for antibacterial activity using disk diffusion technique. The platinum complexes 4 and 5 displayed good resistivity against the following bacteria: Escherichia coli, Proteus penneri, Klebsiella oxytoca and Pseudomonas aeruginosa.

Journal of Bangladesh Academy of Sciences, Vol. 40, No. 1, 65-77, 2016

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Author Biography

Ratan Kumar Paul, Department of Chemistry, Pabna University of Science and Technology, Pabna-6600



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Published

2016-06-22

How to Cite

Paul, R. K., Ahmad, M. F., Khan, M. M. R., & Younus, M. (2016). Synthesis and Antibacterial Activities of Sugar-containing Platinum Ethynyl Complexes. Journal of Bangladesh Academy of Sciences, 40(1), 65–77. https://doi.org/10.3329/jbas.v40i1.28326

Issue

Vol. 40 No. 1 (2016)

Section

Articles