Parallel synthesis of novel benzimidazoles on a soluble polymer support

Central European Journal of Chemistry

Volumn 3, Issue 2, 2005, Pages 288-294

  Chang, Ling Ju ^a   Kulkarni, Manohar V ^a   Sun, Chung Ming ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

Benzimidazoles; Liquid phase synthesis; Molecular diversity; Polymer support

Indexed keywords

EID: 27444447198     PISSN: 16443624     EISSN: 16443624     Source Type: Journal    
DOI: 10.2478/bf02475997     Document Type: Article

References (24)

1. D.J. Gravert and K.D. Janda: "Organic synthesis on soluble polymer supports; Liquid phase methodologies", Chem. Rev, Vol. 97, (1997), pp. 489-509.
2. P.H.H. Hermkens, H.C.J. Ottenheijm and D.C. Rees: "Solid phase organic reactions II", Tetrahedron, Vol. 53, (1997), pp. 5643-5678.
3. C.M. Sun: "Recent advances in Liquid-Phase Combinatorial Chemistry", Comb. Chem. High T. Scr., Vol. 3, (1999), pp. 299-318.
4. C.M. Sun: "Soluble polymer supported synthesis of heterocyclic libraries", In: L. Bellavance (Ed.): Combinatorial chemistry: Methods and Protocols in Molecular Biology Series, The Humana, New Jersey, (2002), Chapter 10, pp. 345-371.
5. A.W. White, R. Almassy, A. Hillary-Clavert, N.J. Curtin, R.J. Griffin, Z. Hostomsky, K. Maegley, D.R. Newell, S. Srinivasan and B.T. Golding: "Resistance modifying agents. 9. Synthesis and biological properties of benzimidazole inhibitors of the DNA repair enzyme poly (ADP-ribose) Polymerase", J. Med. Chem, Vol. 43, (2000), pp. 4084-4097.
6. G.J. Southan and C. Szabo: "Poly(ADP-ribose)Polymerase inhibitors", Current. Med. Chem., Vol. 10, (2003), pp. 321-340.
7. H. Goker, C. Kus, D.W. Boykin, S. Yildiz and M. Altanlar: "Synthesis of some new 2-substituted phenyl-1H- benzimidazole-5-carbonitriles and their potent activity against Candida species", Bioorg. Med. Chem. Lett., Vol. 10, (2002), pp. 2589-2596.
8. S. Ozden, H. Ertepinar and O. Geban: "QSAR study on anti-bacterial effects of benzimidazole and imidazopyridine derivatives", Collect. Czech. Commun., Vol. 60, (1995), pp. 2178-2188.
9. H. Goker, M. Tuncbilek, S. Suzen, C. Kus and N. Altanlar: "Synthesis and antimicrobial activity of some new 2-Phenyl-N-substituted carboxamido-1H-benzimidazole derivatives", Arch. Pharm (Weinheim), Vol. 334, (2001), pp. 148-152.
10. T.E. Voogd, E.L.M. Vansterkenburg, J. Wilting and L.H. Janssen: "Recent research on the biological activity of Suramin", Pharmacol. Rev., Vol. 45, (1993), pp. 177-203.
11. A. Kreimeyer, G. Muller, M. Karsack, P. Nickeland and A.R.T. Gagliardi: "Suramine analogues with a 2-phenylbenzimidazole moiety as a partial structure: Potential HIV and Angiostatic drugs", Arch. Pharm (Weinheim), Vol. 331, (1998), pp. 97-103
12. M. Pedini, G. Alunni-Bistocchi, A. Ricci, L. Bastianini and E. Lepri: "New heterocyclic derivatives of benzimidazole with germicidal activity", Farmaco, Vol. 49, (1994), pp. 823-827.
13. D. Tumelty, K. Cao and C.P. Holmes: "Traceless solid phase synthesis of substituted benzimidazoles via base-cleavable linker", Org. Lett., Vol. 3, (2001), pp. 83-86.
14. K.J. Lee and K.D. Janda: "Traceless solid-phase synthesis of 5-benzoylbenzimidazoles", Can. J. Chem., Vol. 79, (2001), pp. 1556-1561.
15. H. Akamatsu, K. Fukase and S. Kusumoto: "New efficient route for the solid phase synthesis of Benzimidazole derivatives", J. Comb. Chem., Vol. 2, (2002), pp. 475-483.
16. C.G. Blettner, W.A. Konig, G. Ruther, W. Stenzel and T. Schotten: "Paralell synthesis of poly (ethylene) glycol supported biaryl benzimidazoles and imidazopyridines", Synlett., (1999), pp. 309-312.
17. H. Matsushita, S.H. Lee, M. Joung, B. Clepham and K.D. Janda: "Smart cleavage reactions: the synthesis of benzimidazoles and benzothiazoles from polymer bound esters", Tetrahedron Lett., Vol. 45, (2004), pp. 313-317.
18. C.M. Yeh, C.L. Tung and C.M. Sun: "Combinatorial Liquid phase synthesis of Structurally Diverse Benzimidazole Libraries", J. Comb. Chem., Vol. 2, (2000), pp. 341-348.
19. Y.S. Su, M.J. Lin and C.M. Sun: "Mercury chloride assisted cyclisation towards benzimidazoles by focused microwave irradiation", Tetrahedron Lett., Vol. 46, (2005), pp. 177-180.
20. Y.C. Chi and C.M. Sun: "Soluble polymer supported synthesis of benzimidazole library", Synlett., (2000), pp. 591-594.
21. R. Jonas, M. Klockow, I. Lues, H. Prücher, H.J. Schliep and H. Wurziger: "Synthesis and biological activities of meribendan and related heterocyclic benzimidazolo-pyridazinones", Eur. J. Med. Chem., Vol. 28, (1993), pp. 129-140.
22. J.M. Smith and V. Krachňák: "A solid phase traceless synthesis of benzimidazoles with three combinatorial steps", Tetrahedron. Lett., Vol. 40, (1999), pp. 7633-7636.
23. P.L. Beaulieu, B. Haché and E. von Moos: "A Practical Oxone®-mediated, high-throughput, solution-phase synthesis of benzimidazolesfrom 1,2-phenylenediamines and aldehydes and its application to preparative scale synthesis", Synthesis, (2003), pp. 1683-1692
24. 3) for 6c is as follows δ 8.52 (s, 1H); 8.00 (dd, J = 8.7, 1.5 Hz, 1H); 7.67-7.63 (m, 3H); 7.54 (t, J = 3.3 Hz, 3H); 4.87-4.79 (m,J= 6.9 Hz, 1H); 3.96 (s, 3H); 1.66 (d, J = 6.9 Hz, 6H).