Synthesis and Antibacterial Activities of Sugar-containing Platinum Ethynyl Complexes

摘要

New sugar-containing aryl ethynyl ligand [N -(4-trimethylsilylethynylphenyl)- β -D-glucopyranosylamine] 2 has been prepared by the reaction of [ N -(4-iodophenyl)- β -D-glucopyranosylamine] 1 with trimethysilylacetylene in the presence of Pd(OAc) 2 /CuI catalyst, in i Pr 2 NH and DMF solvent mixture. The trimethylsilyl group of compound 2 was deprotected using K 2 CO 3 in methanol to form terminal ethynylene ligand [ N -( β -D-glucopyranosyl)aniline-4-ethyne] 3 . Novel platinum mono-ethynyl complex trans -[(P(Bu) 3 ) 2 PtCl(C≡C-4-C 6 H 4 -NH-D-glocose)] 4 and bis-ethynyl complex trans -[(P(Bu) 3 ) 2 PtCl(C≡C-4-C 6 H 4 -NH-D-glocose)2] 5 were formed by the dehydrohalogenation reaction of trans -[Pt(P(Bu) 3 ) 2 Cl 2 ] with terminal ethynyl ligand 3 in i Pr 2 NH/THF, in the presence of CuI, at 65 o C. The complexes are hygroscopic in air, and are fairly soluble in methanol and CH 2 Cl 2 . 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 Normal 0 false false false MicrosoftInternetExplorer4 New sugar-containing aryl ethynyl ligand [N -(4-trimethylsilylethynylphenyl)- β -D-glucopyranosylamine] 2 has been prepared by the reaction of [ N -(4-iodophenyl)- β -D-glucopyranosylamine] 1 with trimethysilylacetylene in the presence of Pd(OAc) 2 /CuI catalyst, in i Pr 2 NH and DMF solvent mixture. The trimethylsilyl group of compound 2 was deprotected using K 2 CO 3 in methanol to form terminal ethynylene ligand [ N -( β -D-glucopyranosyl)aniline-4-ethyne] 3 . Novel platinum mono-ethynyl complex trans -[(P(Bu) 3 ) 2 PtCl(C ≡C -4-C 6 H 4 -NH-D-glocose)] 4 and bis-ethynyl complex trans -[(P(Bu) 3 ) 2 PtCl(C ≡C -4-C 6 H 4 -NH-D-glocose) 2 ] 5 were formed by the dehydrohalogenation reaction of trans -[Pt(P(Bu) 3 ) 2 Cl 2 ] with terminal ethynyl ligand 3 in i Pr 2 NH/THF, in the presence of CuI, at 65 o C. The complexes are hygroscopic in air, and are fairly soluble in methanol and CH 2 Cl 2 . 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 st1:*{behavior:url(#ieooui) } /* Style Definitions */ table.MsoNormalTable {mso-style-name:"Table Normal"; mso-tstyle-rowband-size:0; mso-tstyle-colband-size:0; mso-style-noshow:yes; mso-style-parent:""; mso-padding-alt:0in 5.4pt 0in 5.4pt; mso-para-margin:0in; mso-para-margin-bottom:.0001pt; mso-pagination:widow-orphan; font-size:10.0pt; font-family:"Times New Roman"; mso-ansi-language:#0400; mso-fareast-language:#0400; mso-bidi-language:#0400;}