Skip to main content
SpringerLink
Log in

Synthesis and biological activity of novel 4- and 6-(1-alkyl/aryl-1H-benzimidazol-2-yl)benzene-1,3-diols

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A one-pot synthesis of new biologically active 4- and 6-(1-alkyl/aryl-1H-benzimidazol-2-yl)benzene-1,3-diols has been developed. The compounds were obtained by the reaction of aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione] with N-substituted benzene-1,2-diamines. Elemental analysis, IR, 1H NMR, 13C NMR, and mass spectral data were used to elucidate their structures. The developed method offers short reaction times, easy and quick isolation of the products, and good yields. The antiproliferative properties of the synthesized compounds were investigated against a panel of human cancer cell lines. Some of the tested compounds showed significant cytotoxic activity.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. Takahashi K, Hashimoto N, Nakama C, Kamata K, Sasaki K, Yoshimoto R, Ohyama S, Hosaka H, Mamki H, Nagata Y, Eiki J, Nishimura T (2009) Bioorg Med Chem 17:7042

    Article  CAS  Google Scholar 

  2. Oren I, Temiz O, Yalcin I, Sener E, Altanlar N (1999) Eur J Pharm Sci 7:153

    Article  CAS  Google Scholar 

  3. Penning TD, Zhu GD, Gong JC, Thomas S, Gandhi VB, Liu XS, Shi Y, Klinghofer V, Johnson EF, Park CH, Fry EH, Donawho CK, Frost DJ, Buchanan FG, Bukofzer GT, Rodriguez LE, Bontcheva-Diaz V, Bouska JJ, Osterling DJ, Olson AM, Marsh KC, Luo Y, Giranda VL (2010) J Med Chem 53:3142

    Article  CAS  Google Scholar 

  4. Zhu GD, Gandhi VB, Gong JC, Thomas S, Luo Y, Liu XS, Shi Y, Klinghofer V, Johnson EF, Frost D, Donawho C, Jarvis K, Bouska J, Marsh KC, Rosenberg SH, Giranda VL, Penning TD (2008) Bioorg Med Chem Lett 18:3955

    Article  CAS  Google Scholar 

  5. Lahue BR, Ma Y, Shipps GW, Seghezzi W, Herbst R (2009) Bioorg Med Chem Lett 19:3405

    Article  CAS  Google Scholar 

  6. Thomas HD, Calabrese CR, Batey MA, Canan S, Hostomsky Z, Kyle S, Maegley KA, Newell DR, Skalitzky D, Wang LZ, Webber SE, Curtin NJ (2007) Mol Cancer Ther 6:945

    Article  CAS  Google Scholar 

  7. Biron KK (2006) Antiviral Res 71:154

    Article  CAS  Google Scholar 

  8. Kraut EH, Fleming T, Segal M, Neidhart JA, Behrens BC, Macdonald J (1991) Invest New Drug 9:95

    CAS  Google Scholar 

  9. Penning TD, Zhu GD, Gandhi VB, Gong JC, Thomas S, Lubisch W, Grandel R, Wernet W, Park CH, Fry EH, Liu XS, Shi Y, Klinghofer V, Johnson EF, Donawho CK, Frost DJ, Bontcheva-Diaz V, Bouska JJ, Olson AM, Marsh KC, Luo Y, Rosenberg SH, Giranda VL (2008) Bioorg Med Chem 16:6965

    Article  CAS  Google Scholar 

  10. Trzebiatowski JR, Escalante Semerena JC (1997) J Biol Chem 272:17662

    Article  CAS  Google Scholar 

  11. Girard CL, Santschi DE, Stabler SP, Allen RH (2009) J Dairy Sci 92:4524

    Article  CAS  Google Scholar 

  12. Fasching M, Schmidt W, Krautler B, Stupperich E, Schmidt A, Kratky C (2000) Helv Chim Acta 83:2295

    Article  CAS  Google Scholar 

  13. Gomez-Romero P, Asensio JA, Borros S (2005) Electrochim Acta 50:4715

    Article  CAS  Google Scholar 

  14. Asensio JA, Borro S, Gomez-Romero P (2004) J Electrochem Soc 151:A304

    Article  CAS  Google Scholar 

  15. Asensio JA, Sanchez EM, Gomez-Romero P (2010) Chem Soc Rev 39:3210

    Article  CAS  Google Scholar 

  16. Asensio JA, Gomez-Romero P (2005) Fuel Cells 5:336

    Article  CAS  Google Scholar 

  17. Schwartz G, Fehse K, Pfeiffer M, Walzer K, Leo K (2006) Appl Phys Lett 89:083509

    Article  Google Scholar 

  18. He Y, Yang J, Wu BG, Risen L, Swayze EE (2004) Bioorg Med Chem Lett 14:1217

    Article  CAS  Google Scholar 

  19. Li YF, Wang GF, He PL, Huang WG, Zhu FH, Gao HY, Tang W, Luo Y, Feng CL, Shi LP, Ren YD, Lu W, Zuo JP (2006) J Med Chem 49:4790

    Article  CAS  Google Scholar 

  20. Tong YS, Bouska JJ, ElIis PA, Johnson EF, Leverson J, Liu XS, Mareotte PA, Olson AM, Osterling DJ, Przytulinska M, Rodriguez LE, Shi Y, Soni N, Stavropoulos J, Thomas S, Donawho CK, Frost DJ, Luo Y, Giranda VL, Penning TD (2009) J Med Chem 52:6803

    Article  CAS  Google Scholar 

  21. Haginoya N, Komoriya S, Osanai K, Yoshino T, Nagata T, Nagamoehi M, Muto R, Yamaguehi M, Nagahara T, Kanno H (2004) Heterocycles 63:1555

    Article  CAS  Google Scholar 

  22. Weidner-Wells MA, Ohemeng KA, Nguyen VN, Fraga-Spano S, Maeielag MJ, Werblood HM, Foleno BD, Webb GC, Barrett JF, Hlasta DJ (2001) Bioorg Med Chem Lett 11:1545

    Article  CAS  Google Scholar 

  23. Bahrami K, Khodaei MM, Naali F (2008) J Org Chem 73:6835

    Article  CAS  Google Scholar 

  24. Bahrami K, Khodaei MM, Naali F (2009) Synlett 569

  25. Zhang ZH, Li TS, Li JJ (2007) Monatsh Chem 138:89

    Article  CAS  Google Scholar 

  26. Yang DL, Fokas D, Li JZ, Yu LB, Baldino CM (2005) Synthesis 47

  27. Ridley HF, Spiekett RG, Timmis GM (1965) J Heterocycl Chem 2:453

    Article  CAS  Google Scholar 

  28. Vitale G, Corona P, Loriga M, Carta A, Paglietti G, La Colla P, Busonera B, Marongiu E, Collu D, Loddo R (2009) Med Chem 5:507

    Article  CAS  Google Scholar 

  29. Brain CT, Brunton SA (2002) Tetrahedron Lett 43:1893

    Article  CAS  Google Scholar 

  30. Evindar G, Batey RA (2003) Org Lett 5:133

    Article  CAS  Google Scholar 

  31. Zheng N, Anderson KW, Huang XH, Nguyen HN, Buehwald SL (2007) Angew Chem Int Ed 46:7509

    Article  CAS  Google Scholar 

  32. Li XF, Yang DS, Jiang YY, Fu H (2010) Green Chem 12:1097

    Article  CAS  Google Scholar 

  33. Wang LM, Sheng J, Tian H, Qian CT (2004) Synth Commun 34:4265

    Article  CAS  Google Scholar 

  34. Loupy A, Petit A, Hamelin J, Texier-Boullet F, Jaequault P, Mathe D (1998) Synthesis 1213

  35. Reddy GV, Rao V, Narsaiah B, Rao PS (2002) Synth Commun 32:2467

    Article  CAS  Google Scholar 

  36. Bougrin K, Loupy A, Petit A, Daou B, Soufiaoui M (2001) Tetrahedron 57:163

    Article  CAS  Google Scholar 

  37. Penieres G, Bonifas I, Lopez JG, Garcia JG, Alvarez C (2000) Synth Commun 30:2191

    Article  CAS  Google Scholar 

  38. Nagawade RR, Shinde DB (2006) Chin Chem Lett 17:453

    CAS  Google Scholar 

  39. Nagawade RR, Shinde DB (2007) Indian J Chem Sect B Org Chem Incl Med Chem 46:349

    Google Scholar 

  40. Matysiak J, Niewiadomy A (2006) Synth Commun 36:1621

    Article  CAS  Google Scholar 

  41. Tavman A, Birteksoz AS (2009) Rev Inorg Chem 29:255

    Article  CAS  Google Scholar 

  42. Matysiak J (2006) Bioorg Med Chem 14:2613

    Article  CAS  Google Scholar 

  43. Kreusch A, Han SL, Brinker A, Zhou V, Choi HS, He Y, Lesley SA, Caldwell J, Gu X-J (2005) Bioorg Med Chem Lett 15:1475

    Article  CAS  Google Scholar 

  44. Brough PA, Barril X, Beswick M, Dymock BW, Drysdale MJ, Wright L, Grant K, Massey A, Surgenor A, Workman P (2005) Bioorg Med Chem Lett 15:5197

    Article  CAS  Google Scholar 

  45. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990) J Natl Cancer Inst 8:1107

    Google Scholar 

  46. Nevozhay D (2007) Cheburator 0.9.0

Download references

Author information

Authors and Affiliations

  1. Institute of Industrial Organic Chemistry in Warsaw, Warsaw, Poland

    Monika M. Karpińska & Andrzej Niewiadomy

  2. Department of Chemistry, University of Life Sciences in Lublin, Akademicka 15, 20-950, Lublin, Poland

    Joanna Matysiak & Andrzej Niewiadomy

  3. Department of Experimental Oncology, Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, R. Weigla 12, 53-114, Wrocław, Poland

    Joanna Wietrzyk & Dagmara Kłopotowska

Authors
  1. Monika M. Karpińska
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Joanna Matysiak
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Andrzej Niewiadomy
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Joanna Wietrzyk
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Dagmara Kłopotowska
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Joanna Matysiak.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Karpińska, M.M., Matysiak, J., Niewiadomy, A. et al. Synthesis and biological activity of novel 4- and 6-(1-alkyl/aryl-1H-benzimidazol-2-yl)benzene-1,3-diols. Monatsh Chem 143, 269–276 (2012). https://doi.org/10.1007/s00706-011-0665-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0665-5

Keywords

Search

Navigation