Synthesis of Novel Bithiophene-Substituted Heterocycles Bearing Carbonitrile Groups

REFERENCES

• (a) Fichou , D. Handbook of Oligo- and Polythiophenes ; Wiley-VCH : Weinheim , Germany , 1999 ; (b) Ong, B. S.; Wu, Y.; Liu, P.; Gardner, S. High-performance semiconducting polythiophenes for organic thin-film transistors. J. Am. Chem. Soc., 2004, 126, 3378–3379; (c) Chang, P. C.; Lee, J.; Huang, D.; Subramanian, V.; Murphy, A. R.; Frechet, J. M. J. Film morphology and thin film transistor performance of solution processed oligothiophenes. Chem. Mater. 2004, 16, 4783–4789; (d) Fichou, D. Structural order in conjugated oligothiophenes and its implications on opto-electronic devices. J. Mater. Chem. 2000, 10, 571–588; (e) Negishi, N.; Takimiya, K.; Otsubo, T.; Harima, Y.; Aso, Y. Synthesis and photovoltaic effects of oligothiophenes incorporated with two [60]fullerenes. Chem. Lett. 2004, 33, 654–655 .
   Google Scholar
• Taylor , R. In Thiophene and Its Derivatives , S. Gronowitz (Ed.); Wiley : New York , 1985 ; vol. 44 (part 1), ch. 3 .
   Google Scholar
• Tidwell , R. R. ; Boykin , D. W. Dicationic DNA minor groove binders as antimicrobial agents . In Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes , M. Demeunynck , C. Bailly , W. D. Wilson (Eds.); Wiley-VCH : New York , 2003 ; vol. 2 , 416 – 460 .
   Google Scholar
• Wilson , W. D. ; Nguyen , B. ; Tanious , F. A. ; Mathis , A. ; Hall , J. E. ; Stephens , C. E. ; Boykin , D. W. Dications that target the DNA minor groove: Compound design and preparation, DNA interactions, cellular distribution and biological activity. Curr. Med. Chem.-Anti-Cancer Agents 2005, 5, 389–408.
   PubMedGoogle Scholar
• Soeiro , M. N. C. ; de Souza , E. M. ; Stephens , C. E. ; Boykin , D. W. Aromatic diamidines as antiparasitic agents . Expert. Opin. Invest. Drugs 2005 , 14 , 957 – 972 .
   PubMed Web of Science ®Google Scholar
• Wenzler , T. ; Boykin , D. W. ; Ismail , M. A. ; Hall , J. E. ; Tidwell , R. R. ; Brun , R. New treatment option for second-stage African sleeping sickness: In vitro and in vivo efficacy of aza analogs of DB289 . Antimicrob. Agents Chemother . 2009 , 53 ( 10 ), 4185 – 4192 .
   PubMedGoogle Scholar
• White , E. W. ; Tanious , F. A. ; Ismail , M. A. ; Reszka , A. P. ; Neidle , S. ; Boykin , D. W. ; Wilson , D. W. Structure specific recognition of quadruplex DNA by organic cations: Influence of shape, substituents and charge . Biophys. Chem. 2007 , 126 , 140 – 153 .
   PubMedGoogle Scholar
• Batista , D. G. ; Pacheco , M. G. ; Kumar , A. ; Branowska , D. ; Ismail , M. A. ; Hu , L. ; Boykin , D. W. ; Soeiro , M. N. Biological, ultrastructural effect, and subcellular localization of aromatic diamidines in . Trypanosoma cruzi. Parasitology 2009 , 21 , 1 – 9 .
   Google Scholar
• Ismail , M. A. ; Boykin , D. W. ; Stephens , C. E. An efficient synthesis of 5,5′-diaryl-2,2′-bichalcophenes . Tetrahedron Lett. 2006 , 47 , 795 – 797 .
   Web of Science ®Google Scholar
• Ismail , M. A. An efficient synthesis of 5′-(4-cyanophenyl)-2,2′-bifuran-5-carbonitrile and analogues . J. Chem. Res. 2006 , 733 – 737 .
   Google Scholar
• Ismail , M. A. ; Brun , R. ; Easterbrook , J. D. ; Tanious , F. A. ; Wilson , D. W. ; Boykin , D. W. Synthesis and antiprotozoal activity of aza-analogues of furamidine . J. Med. Chem. 2003 , 46 . 4761 – 4769 .
   PubMed Web of Science ®Google Scholar
• (a) Ismail , M. A. ; Arafa , R. K. ; Wenzler , T. ; Brun , R. ; Tanious , F. A. ; Wilson , D. W. ; Boykin , D. W. Synthesis and antiprotozoal activity of novel bis-benzamidino imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydroimidazo[1,2-a]pyridines . Bioorg. Med. Chem. 2008 , 16 , 683 – 691 ; (b) Ismail , M. A. ; Brun , R. ; Wenzler , T. ; Tanious , F. A. ; Wilson , W. D. ; Boykin , D. W. Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines as antiprotozoal agents . J. Med. Chem. 2004 , 47 , 3658 – 3664 .
   PubMed Web of Science ®Google Scholar
• (a) Ismail , M. A. ; Miao , Y. ; Wilson , D. W. ; Wenzler , T. ; Brun , R. ; Boykin , D. W. Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents . Bioorg. Med. Chem. 2005 , 13 , 6718 – 6726 ; (b) Ismail , M. A. ; Brun , R. ; Wenzler , T. ; Tanious , F. A. ; Wilson , D. W. ; Boykin , D. W. Dicationic biphenyl benzimidazole derivatives as antiprotozoal agents . Bioorg. Med. Chem. 2004 , 12 , 5405 – 5413 .
   PubMed Web of Science ®Google Scholar
• Wang , C. C. Molecular mechanisms and therapeutic approaches to the treatment of african trypanosomiasis . Annu. Rev. Pharmacol. Toxicol. 1995 , 35 , 93 – 127 .
   PubMed Web of Science ®Google Scholar
• (a) El Kazzouli , S. ; Berthault , A. ; Berteina-Raboin , S. ; Mouaddib , A. ; Guillaumet , G. Solution and solid-phase functionalization of imidazo[1,2-a]pyridines . Lett. Org. Chem. 2005 , 2 , 184 – 187 ; (b) Salgado-Zamora , H. ; Velazquez , M. ; Mejia , D. ; Campos-Aldrete , M. E. ; Jimenez , R. ; Cervantes , H. Influence of the 2-aryl group on the ipso electrophilic substitution process of 2-arylimidazo[1,2-a]pyridines . Heterocyclic Commun. 2008 , 14 ( 1–2 ), 27 – 32 .
   Google Scholar
• Zhu , S. S. ; Swager , T. M. Conducting polymetallorotaxanes: Metal ion–mediated enhancements in conductivity and charge localization . J. Am. Chem. Soc. 1997 , 119 , 12568 – 12577 .
   Web of Science ®Google Scholar
• Hucke , A. ; Cava , M. P. Synthesis of mixed thiophene/furan oligomers by Stille coupling . J. Org. Chem. 1998 , 63 , 7413 – 7417 .
   PubMed Web of Science ®Google Scholar
• Bagli , J. F. ; Ferdinandi , E. Thiophene isosters of phenylethanolamines . Can. J. Chem. 1975 , 53 , 2598 – 2607 .
   Google Scholar
• Batista , R. M. F. ; Costa , S. P. G. ; Belsley , M. ; Lodeiro , C. ; Raposo , M. M. Synthesis and characterization of novel (oligo) thienyl-imidazo-phenanthrolines as versatile π-conjugated systems for several optical applications . Tetrahedron 2008 , 64 , 9230 – 9238 .
   Web of Science ®Google Scholar
• Mitsumori , T. ; Inoue , K. ; Koga , N. ; Iwamura , H. Exchange interactions between two nitronyl nitroxide or iminyl nitroxide radicals attached to thiophene and 2,2′-bithienyl rings . J. Am. Chem. Soc. 1995 , 117 , 2467 – 2478 .
   Web of Science ®Google Scholar