Organoselenium compounds containing pyrazole or phenylthiazole groups: Synthesis,structure, tin(IV) complexes and antiproliferative activity |
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Authors: | Roxana A Popa Emilia Licarete Manuela Banciu Anca Silvestru |
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Institution: | 1. Centre of Supramolecular Organic and Organometallic Chemistry, Department of Chemistry, Faculty of Chemistry and Chemical Engineering, Babe?‐Bolyai University, Cluj‐Napoca, Romania;2. Department of Molecular Biology and Biotechnology, Faculty of Biology and Geology, Babe?‐Bolyai University, Cluj‐Napoca, Romania;3. Molecular Biology Centre, Institute for Interdisciplinary Research in Bio‐Nano‐Sciences, Babe?‐Bolyai University, Cluj‐Napoca, Romania |
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Abstract: | The diorganodiselenides (pzCH2CH2)2Se2 ( 1 ) and (PhtzCH2)2Se2 ( 2 ) were prepared by reacting Na2Se2 with 1‐(2‐bromoethyl)‐1H‐pyrazole and 4‐(chloromethyl)‐2‐phenylthiazole, respectively, while the reactions between 1‐(2‐bromoethyl)‐1H‐pyrazole or 4‐(chloromethyl)‐2‐phenylthiazole and the lithium organoselenolates 2‐(Et2NCH2)C6H4]SeLi and 2‐{O(CH2CH2)2NCH2}C6H4]SeLi in a 1:1 molar ratio resulted in the heteroleptic diorganoselenium(II) compounds 2‐(Et2NCH2)C6H4](R)Se (R = pzCH2CH2 ( 3 ) or PhtzCH2 ( 5 )) and 2‐{O(CH2CH2)2NCH2}C6H4](R)Se (R = pzCH2CH2 ( 4 ) or PhtzCH2 ( 6 )). The diorganotin(IV) bis(organoselenolato) derivatives of type R2Sn(SeCH2CH2pz)2 (R = 2‐(Me2NCH2)C6H4 ( 7 ) or Me ( 8 )) were obtained by reacting (pzCH2CH2)SeNa with the appropriate diorganotin(IV)dichloride in a 2:1 molar ratio. All compounds were investigated using NMR spectroscopy (1H, 13C, 77Se, 119Sn as appropriate) and ESI+ mass spectrometry. The molecular structures of 2 and 6 were determined using single‐crystal X‐ray diffraction. The formation of a 10–Se–3 hypercoordinated species was evidenced for 6 in the solid state, as a consequence of the C,N coordination behaviour of the 2‐{O(CH2CH2)2NCH2}C6H4 group. Compounds 1 , 7 and 8 were investigated for their antiproliferative activity towards the mouse colon carcinoma C26 cell line with the preliminary results showing a better activity than 5‐fluorouracil. |
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Keywords: | antiproliferative activity diorganodiselenides diorganotin(IV) bis(organoselenolato) derivatives heteroleptic diorganoselenium(II) compounds structural investigation |
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