Skip to main content
SpringerLink
Log in

Synthesis and biological evaluation of 5-substituted benzo[b]thiophene derivatives as anti-inflammatory agents

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

Abstract

5-Aminobenzo[b]thiophene-2-carboxylic acid was converted to the corresponding 5-(2-chloroacetamido)benzo[b]thiophene-2-carboxylic acid by reaction with chloroacetyl chloride. This acetamido product was treated with different alkyl, cycloalkyl, aryl, and heterocyclic amines to afford a series of C5-substituted benzo[b]thiophenes. These compounds were found to possess potent anti-inflammatory 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
Scheme 3
Fig. 1

Similar content being viewed by others

References

  1. Vane JR (1971) Nat New Biol 231:232

    CAS  Google Scholar 

  2. Vane JR, Botting RM (1998) Inflamm Res 47:S78

    Article  CAS  Google Scholar 

  3. Perini R, Fiorucci R, Wallace JL (2004) Can J Gastroenterol 18:229

    Google Scholar 

  4. Penning TD, Tally JJ, Bertenshaw SR, Carter JS, Collins PW, Doctor S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC (1997) J Med Chem 40:1347

    Article  CAS  Google Scholar 

  5. Prasit P, Wang Z, Brideau C, Chan CC, Charleson S, Cromlish W, Ethier D, Evans JF, Ford-Hutchinson AW, Gauthier JY, Gordon R, Guay J, Gresser M, Kargman S, Kennedy B, Leblanc Y, Léger S, Mancini J, O’Neill GP, Quellet M, Percival MD, Perrier H, Riendeau D, Rodger I, Tagari P, Therien M, Vickers P, Wong E, Xu LJ, Young RN, Zamboni R, Boyce S, Rupniak N, Forrest M, Visco D, Patrick D (1999) Bioorg Med Chem Lett 9:1773

    Article  CAS  Google Scholar 

  6. Hsiao CN, Kolasa T (1992) Tetrahedron Lett 33:2629

    Article  CAS  Google Scholar 

  7. Jordan VC (2003) J Med Chem 46:1081

    Article  CAS  Google Scholar 

  8. Sall DJ, Bastian JA, Briggs SL, Buben JA, Chirgadze NY, Clawson DK, Denney ML, Giera DD, Gifford-Moore DS, Harper RW, Hauser KL, Klimkowski VJ, Kohn TJ, Lin HS, Mc Cowan JR, Palkowitz AD, Smith GF, Takeuchi K, Thrasher KJ, Tinsley JM, Utterback BG, Yan SC, Zhang M (1997) J Med Chem 40:3489

    Article  CAS  Google Scholar 

  9. Johnson MG, Bronson DD, Gillespie JE, Gifford-Moore DS, Kalter K, Lynch MP, McCowan JR, Redick CC, Sall DJ, Smith GF, Foglesong RJ (1999) Tetrahedron 55:11641

    Article  CAS  Google Scholar 

  10. Chou YL, Davey DD, Eagen KA, Griedel BD, Karanjawala R, Phillips GB, Sacchi KL, Shaw KJ, Wu SC, Lentz D, Liang AM, Trinh L, Morrissey MM, Kochanny MJ (2003) Bioorg Med Chem Lett 13:507

    Article  CAS  Google Scholar 

  11. Maignan S, Guilloteau JP, Choi-Sledeski YM, Becker MR, Ewing WR, Pauls HW, Spada AP, Mikol V (2003) J Med Chem 46:685

    Article  CAS  Google Scholar 

  12. Shrader WD, Young WB, Sprengeler PA, Sangalang JC, Elrod K, Carr G (2001) Bioorg Med Chem Lett 11:1801

    Article  CAS  Google Scholar 

  13. Qiao JX, Cheng X, Modi DP, Rossi KA, Luettgen JM, Knabb RM, Jadhav PK, Wexler RR (2005) Bioorg Med Chem Lett 15:29

    Article  CAS  Google Scholar 

  14. Fenwick AE, Garnier B, Gribble AD, Ife RJ, Rawlings AD, Witherington J (2001) Bioorg Med Chem Lett 11:195

    Article  CAS  Google Scholar 

  15. Fakhr I M, Radwan MA, El-Batran S, Abd El-Salam OM, El-Shenawy SM (2008) Eur J of Med Chem (in press)

  16. Martin-Smith M, Reid ST (1960) J Chem Soc 938

  17. Zambias RA, Hammond ML (1991) Synth Commun 21:959

    Article  CAS  Google Scholar 

  18. Perez-Silanes S, Martinez-Esparza J, Oficialdequi AM, Villanueva H, Orus L, Monge A (2001) J Heterocyclic Chem 38:1025

    Article  CAS  Google Scholar 

  19. Winter CA, Risley EA, Nuss GW (1962) Proc Soc Exp Biol Med 111:544

    CAS  Google Scholar 

  20. Obukowicz MG, Welsch DJ, Salsgiver WJ, Martin-Berger CL, Chinn KS, Duffin KL, Raz A, Needleman P (1998) J Pharmacol Exp Ther 287:157

    CAS  Google Scholar 

  21. Rani P, Srivastava VK, Kumar A (2004) Eur J Med Chem 39:449

    Article  CAS  Google Scholar 

  22. Paget GE, Barnes JM (1964) Evaluation of drug activities pharmacometics. Academic Press, New York, p 1

    Google Scholar 

  23. Souza SM, Aquino LC, Milach AC Jr, Bandeira MA, Nobre ME, Viana GS (2007) Phytother Res 21:220

    Article  CAS  Google Scholar 

  24. Robert A, Nezamis JE, Lancaster C, Hanchar AJ (1979) Gastroenterology 77:433

    CAS  Google Scholar 

  25. Mózsik G, Morón F, Jávor T (1982) Prostaglandins Leukot Med 9:71

    Article  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the Central Services Unit (National Research Center, Cairo, Egypt) for obtaining the spectral data.

Author information

Authors and Affiliations

  1. Applied Organic Chemistry Department, National Research Centre, Dokki, Cairo, Egypt

    Mohamed A. A. Radwan & Marwa A. Shehab

  2. Pharmacology Department, National Research Centre, Dokki, Cairo, Egypt

    Siham M. El-Shenawy

Authors
  1. Mohamed A. A. Radwan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marwa A. Shehab
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Siham M. El-Shenawy
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohamed A. A. Radwan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Radwan, M.A.A., Shehab, M.A. & El-Shenawy, S.M. Synthesis and biological evaluation of 5-substituted benzo[b]thiophene derivatives as anti-inflammatory agents. Monatsh Chem 140, 445–450 (2009). https://doi.org/10.1007/s00706-008-0067-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-008-0067-5

Keywords

Search

Navigation