%0 Journal Article
%T Synthesis, Electrochemistry and Antitumor Activity of 1¡¯H, 3¡¯H(Me)-spiro-[(aza)benzimidazoline-2¡¯, 3-(1,2-diferrocenylcyclopropenes)], 2-(1,2-Diferrocenylvinyl)benz- and Azabenzimidazoles
%A Jessica J. S¨¢nchez Garc¨ªa
%A Luis Ortiz-Frade
%A Elena Mart¨ªnez-Klimova
%A Juan C. Garc¨ªa Ramos
%A Marcos Flores-Alamo
%A Teresa Ram¨ªrez Apan
%A Elena I. Klimova
%J Open Journal of Synthesis Theory and Applications
%P 44-56
%@ 2168-1252
%D 2014
%I Scientific Research Publishing
%R 10.4236/ojsta.2014.34007
%X A new
method of synthesis of 2-(1,2-diferrocenylvinyl)benz- and azabenzimidazoles
(3a-f), (4a-f) and 1¡¯H,3¡¯H(Me)-spiro-[(aza)benzimidazoline-2¡¯,3-(1,2-diferrocenylcyclopropenes)]
(5a-f) </span><a name=\"OLE_LINK50\"></a><a name=\"OLE_LINK49\"></a><span style=\"font-size:10.0pt;font-family:&quot;\">via</span><span style=\"font-size:10.0pt;font-family:&quot;\"> reactions of diferrocenyl(methylsulfanyl)cyclopropenylium
iodide (1) with aromatic <i>o</i>-diamines
(2a-f) in the presence of Et<sub>3</sub>N (80</span><span style=\"font-size:10.0pt;font-family:&quot;\">¡ãC</span><span style=\"font-size:10.0pt;font-family:&quot;\"> - 82</span><span style=\"font-size:10.0pt;font-family:&quot;\">¡ãC</span><span style=\"font-size:10.0pt;font-family:&quot;\">) is described. The
structures of the resultant compounds are established using IR, <sup>1</sup>H
and <sup>13</sup>C NMR spectroscopy, mass spectrometry and elemental analysis.
The structure of one compound, <i>cis</i>-2-(1,2-diferrocenylvinyl)-1-methylbenzimidazole
(3b), is confirmed by X-ray diffraction analysis. </span><span style=\"font-size:10.0pt;font-family:&quot;\">The electrochemical
properties of compounds 3a, 3b, 3d and 5f a</span><span style=\"font-size:10.0pt;font-family:&quot;\">re investigated using cyclic square wave
voltammetry. Two electrochemical processes (I-II), attributed to oxidation of
the ferrocene moieties, and the values of </span><span style=\"font-size:10.0pt;font-family:&quot;\">E</span><sup><span style=\"font-size:10.0pt;font-family:&quot;\">0¡¯</span></sup><span style=\"font-size:10.0pt;font-family:&quot;\">(I), E</span><sup><span style=\"font-size:10.0pt;font-family:&quot;\">0¡¯</span></sup><span style=\"font-size:10.0pt;font-family:&quot;\">(II)</span><span style=\"font-size:10.0pt;font-family:&quot;\">, </span><span style=\"font-size:10.0pt;font-family:Symbol;\">D</span><span style=\"font-size:10.0pt;font-family:&quot;\">E</span><sup><span style=\"font-size:10.0pt;font-family:&quot;\">0¡¯</span></sup><span style=\"font-size:10.0pt;font-family:&quot;\">(II-I) and <a name=\"OLE_LINK46\"></a><a name=\"OLE_LINK45\"></a>comporportionation constant K<sub>com</sub> are reported. The bioactivities of seven compounds 3a,
3c-f, 5d, 5f are evaluated. Compound 5f is the most active compound with a
modest cytotoxic activity against six human cancer cell lines: U-251 (glioma),
PC-3 (prostate cancer), K-562 (leukemia), HCT-15 (colon cancer), MCF-7 (breast
cancer) and SKLU-1 (lung cancer).
%K Diferrocenyl(methylthio)cyclopropenylium
%K 2-(1
%K 2-Diferrocenylvinyl)(aza)benzimidazoles
%K 1¡¯H
%K 3¡¯H(Me)-spiro-[(aza)benzimidazoline-2¡¯
%K 3-(1
%K 2-diferrocenylcyclopropenes)]
%K Electrochemistry
%K Antitumor Activity
%U http://www.scirp.org/journal/PaperInformation.aspx?PaperID=50744