Spectroscopic characterization, crystal structure determination and interaction with DNA of novel cyano substituted benzimidazole derivative
- 155 Downloads
Novel cyano-substituted benzimidazole derivatives 3 and 4 were synthesized from 4-N,N-dimethylamino-benzaldehyde and 2-cyanomethyl-benzimidazole. 2-(1H-benzimidazol-2-yl)-3-(4-N,N-dimethylamino-phenyl)-acrylonitrile hydrochloride monohydrate 4 has been studied by 1H and 13C NMR, IR, MS, UV/Vis and fluorescence spectroscopy and confirmed by X-ray crystal structure analysis. The interaction of 4 with ct-DNA has also been investigated by fluorescence spectroscopy and melting temperature determination experiment. According to the emission spectra recorded in the absence and presence of ct-DNA at different ratios r ([compound]/[polynucleotide]), 4 showed marked decrease in the fluorescence intensity and very strong hypochromic effect. Melting temperature experiment showed weak stabilization of double helix. To determine binding mode of 4, other additional experiments are necessary. The molecules of 4 are almost planar with the dihedral angle between benzimidazole and phenyl rings of 6.99(6)°. The protonation of nitrogen atom of benzimidazole ring is followed by π-electrons delocalization in the region resulting in C–N bond distances equality [1.341(2) and 1.337(2) Å]. Both NH groups of benzimidazole ring form intermolecular hydrogen bonds, one with the oxygen atom of water molecule [N···O 2.689(2) Å] and the other with Cl− ion (N···Cl− 3.051(1) Å). Except proton acceptor, water molecule acts as double proton donor in the formation of intermolecular hydrogen bonds with Cl− ion [O···Cl− 3.126(2) and 3.169(2) Å]. In that way, infinite chains along  direction are formed.
KeywordsBenzimidazole derivatives Synthesis Spectroscopic characterization Crystal structure determination Interaction with ct-DNA
The Ministry of Science and Technology of the Republic of Croatia, Zagreb (grant Nos. 119-1193079-1332 and 125-0982464-1356) supported this work.
- 2.El-Hawash SAM, Badawey E, Kappe O (1999) Pharmazie 54:341Google Scholar
- 9.Brana MF,Castellano JM,Keilhauer G, Machuca A, Martín Y, Redondo C, Schlick E, Walker N (1994) Anticancer Drug Des 9:527Google Scholar
- 13.Hranjec M, Starčević K, Zamola B, Mutak S, Đerek M, Karminski-Zamola G (2002) J Antibiotics 55:308Google Scholar
- 15.Starčević K, Boykin DW, Karminski-Zamola G (2002) Heterocyclic Comm 8:221Google Scholar
- 16.Bailly C (2000) Curr Med Chem 7:39Google Scholar
- 17.Demeunynck M, Bailly C, Wilson WD (2002) In DNA and RNA binders. Wiley-VCH, WeinheimGoogle Scholar
- 23.Oxford Diffraction (2004) Oxford Diffraction Ltd., Xcalibur CCD system, CrysAlis Software system, Version 171.23Google Scholar
- 24.Sheldrick GM (1997) SHELXS97 and SHELXL97. University of Göttingen, GermanyGoogle Scholar
- 25.Spek AL (1990) Acta Cryst A46:34Google Scholar
- 26.Buechi J, Zwicky H, Aebi A (1960) Archiv der Pharmazie 8:759Google Scholar
© Springer Science+Business Media, LLC 2007