Synthesis and Antibacterial Activities of Sugar-containing Platinum Ethynyl Complexes

Ratan Kumar Paul, Md Faruak Ahmad, Mohammad Mizanur Rahman Khan, Muhammad Younus
2016 Journal of Bangladesh Academy of Sciences  
<p>New sugar-containing aryl ethynyl ligand [N-(4-trimethylsilylethynylphenyl)-β-D-glucopyranosylamine] <strong>2 </strong>has been prepared by the reaction of [N-(4-iodophenyl)-β-D-glucopyranosylamine] <strong>1 </strong>with trimethysilylacetylene in the presence of Pd(OAc)<sub>2</sub>/CuI catalyst, in <sup>i</sup>Pr<sub>2</sub>NH and DMF solvent mixture. The trimethylsilyl group of compound <strong>2 </strong>was deprotected using K<sub>2</sub>CO<sub>3</sub> in methanol to form terminal
more » ... form terminal ethynylene ligand [N-(β-D-glucopyranosyl)aniline-4-ethyne] <strong>3</strong>. Novel platinum mono-ethynyl complex trans-[(P(Bu)<sub>3</sub>)<sub>2</sub>PtCl(C≡C-4-C<sub>6</sub>H<sub>4</sub>-NH-D-glocose)] <strong>4 </strong>and bis-ethynyl complex trans-[(P(Bu)<sub>3</sub>)<sub>2</sub>PtCl(C≡C-4-C<sub>6</sub>H<sub>4</sub>-NH-D-glocose)2] <strong>5 </strong>were formed by the dehydrohalogenation reaction of trans-[Pt(P(Bu)<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>] with terminal ethynyl ligand <strong>3 </strong>in <sup>i</sup>Pr<sub>2</sub>NH/THF, in the presence of CuI, at 65<sup>º</sup>C. The complexes are hygroscopic in air, and are fairly soluble in methanol and CH<sub>2</sub>Cl<sub>2</sub>. The new compound <strong>2 - 5 </strong>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 <strong>4 </strong>and <strong>5 </strong>displayed good resistivity against the following bacteria: Escherichia coli, Proteus penneri, Klebsiella oxytoca and Pseudomonas aeruginosa.</p><p>Journal of Bangladesh Academy of Sciences, Vol. 40, No. 1, 65-77, 2016</p><!--[if gte mso 9]><xml> <w:WordDocument> <w:View>Normal</w:View> <w:Zoom>0</w:Zoom> <w:PunctuationKerning/> <w:ValidateAgainstSchemas/> <w:SaveIfXMLInvalid>false</w:SaveIfXMLInvalid> <w:IgnoreMixedContent>false</w:IgnoreMixedContent> <w:AlwaysShowPlaceholderText>false</w:AlwaysShowPlaceholderText> <w:Compatibility> <w:BreakWrappedTables/> <w:SnapToGridInCell/> <w:WrapTextWithPunct/> <w:UseAsianBreakRules/> <w:DontGrowAutofit/> </w:Compatibility> <w:BrowserLevel>MicrosoftInternetExplorer4</w:BrowserLevel> </w:WordDocument> </xml><![endif]--><p class="MsoNormal"><span style="font-size: 8.5pt;">New sugar-containing aryl ethynyl ligand [N-(4-trimethylsilylethynylphenyl)-</span><span style="font-size: 8.5pt; font-family: TimesNewRomanPS-ItalicMT; mso-bidi-font-family: TimesNewRomanPS-ItalicMT;">β</span><span style="font-size: 8.5pt;">-D-glucopyranosylamine] <strong>2 </strong>has been prepared by the reaction of [N-(4-iodophenyl)-</span><span style="font-size: 8.5pt; font-family: TimesNewRomanPS-ItalicMT; mso-bidi-font-family: TimesNewRomanPS-ItalicMT;">β</span><span style="font-size: 8.5pt;">-D-glucopyranosylamine] <strong>1 </strong>with trimethysilylacetylene in the presence of Pd(OAc)</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">/CuI catalyst, in </span><sup><span style="font-size: 5.5pt;">i</span></sup><span style="font-size: 8.5pt;">Pr</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">NH and DMF solvent mixture. The trimethylsilyl group of compound <strong>2 </strong>was deprotected using K</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">CO</span><sub><span style="font-size: 5.5pt;">3</span></sub><span style="font-size: 8.5pt;">in methanol to form terminal ethynylene ligand [N-(</span><span style="font-size: 8.5pt; font-family: TimesNewRomanPS-ItalicMT; mso-bidi-font-family: TimesNewRomanPS-ItalicMT;">β</span><span style="font-size: 8.5pt;">-D-glucopyranosyl)aniline-4-ethyne] <strong>3</strong>. Novel platinum mono-ethynyl complex trans-[(P(Bu)</span><sub><span style="font-size: 5.5pt;">3</span></sub><span style="font-size: 8.5pt;">)</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">PtCl(C</span><span style="font-size: 8.5pt; font-family: TimesNewRomanPSMT; mso-bidi-font-family: TimesNewRomanPSMT;">≡C</span><span style="font-size: 8.5pt;">-4-C</span><sub><span style="font-size: 5.5pt;">6</span></sub><span style="font-size: 8.5pt;">H</span><sub><span style="font-size: 5.5pt;">4</span></sub><span style="font-size: 8.5pt;">-NH-D-glocose)] <strong>4 </strong>and bis-ethynyl complex trans-[(P(Bu)</span><sub><span style="font-size: 5.5pt;">3</span></sub><span style="font-size: 8.5pt;">)</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">PtCl(C</span><span style="font-size: 8.5pt; font-family: TimesNewRomanPSMT; mso-bidi-font-family: TimesNewRomanPSMT;">≡C</span><span style="font-size: 8.5pt;">-4-C</span><sub><span style="font-size: 5.5pt;">6</span></sub><span style="font-size: 8.5pt;">H</span><sub><span style="font-size: 5.5pt;">4</span></sub><span style="font-size: 8.5pt;">-NH-D-glocose)</span><span style="font-size: 5.5pt;">2</span><span style="font-size: 8.5pt;">] <strong>5 </strong>were formed by the dehydrohalogenation reaction of trans-[Pt(P(Bu)</span><sub><span style="font-size: 5.5pt;">3</span></sub><span style="font-size: 8.5pt;">)</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">Cl</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">] with terminal ethynyl ligand <strong>3 </strong>in </span><sup><span style="font-size: 5.5pt;">i</span></sup><span style="font-size: 8.5pt;">Pr</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">NH/THF, in the presence of CuI, at 65<sup>º</sup>C. The complexes are hygroscopic in air, and are fairly soluble in methanol and CH</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">Cl</span><sub><span style="font-size: 5.5pt;">2</span></sub><span style="font-size: 8.5pt;">. The new compound <strong>2 - 5 </strong>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 <strong>4 </strong>and <strong>5 </strong>displayed good resistivity against the following bacteria: Escherichia coli, Proteus penneri, Klebsiella oxytoca and Pseudomonas aeruginosa.</span></p><p class="MsoNormal">Journal of Bangladesh Academy of Sciences, Vol. 40, No. 1, 65-77, 2016</p><!--[if gte mso 9]><xml> <w:LatentStyles DefLockedState="false" LatentStyleCount="156"> </w:LatentStyles> </xml><![endif]--><!--[if !mso]><object classid="clsid:38481807-CA0E-42D2-BF39-B33AF135CC4D" id=ieooui></object> <style> st1\:*{behavior:url(#ieooui) } </style> <![endif]--><!--[if gte mso 10]> <style> /* 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;} </style> <![endif]-->
doi:10.3329/jbas.v40i1.28326 fatcat:c622fwdozrf3jkmvk5zbkjc2wu