Skip to main content
SpringerLink
Log in

Pyrrole Natural Products with Antitumor Properties

  • Chapter
  • First Online:
Heterocyclic Antitumor Antibiotics

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 2))

Abstract

This review examines the antitumor activity and synthetic strategies for pyrrole-containing natural products possessing the oxygenated 3,4-diaryl or 3,4-diheteroaryl substitution pattern during the period of 1995–2005. The specific pyrrole-containing natural products are discussed in an order according to their characteristic structural features, which include the dihydroisoquinoline and δ-lactone framework in some cases. The presence or absence of methoxy or hydroxy groups at appropriate positions on aromatic rings or heteroaromatic rings is discussed and such factors have been correlated to antitumor activity and multidrug resistance reversal activity for various structural classes.

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

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

DMFA:

N,N-dimethylformamide dimethylacetal

DPPA:

Diphenylphosphorylazide

ED50 :

Effective dose for 50% inhibition of cell culture growth

MDR:

Multi drug resistance

MIC:

Minimum inhibitory concentration

PTSA:

p-Toluenesulfonic acid

References

  1. Newman DJ, Cragg GM, Snader KM (2003) J Nat Prod 66:1022

    Article  PubMed  CAS  Google Scholar 

  2. Schwartsmann G, Rocha A, Mattei J, Lopes RM (2003) Expert Opin Inv Drug 12:1367

    Article  CAS  Google Scholar 

  3. Urban S, Hickfod S, Blunt J, Munro M (2000) Curr Org Chem 4:765

    Article  CAS  Google Scholar 

  4. Kuramaoto M, Arimoto H, Uemura D (2004) Mar Drugs 2:39

    Article  Google Scholar 

  5. Fernandez D, Ahaidar A, Danelon G, Cironi P, Marfil M, Perez O, Cuevas C, Albericio F, Joule J, Alvarez M (2004) Monat Chem 135:615

    CAS  Google Scholar 

  6. Yoshida W, Lee K, Carroll A, Scheuer P (1992) Helv Chim Acta 75:1721

    Article  CAS  Google Scholar 

  7. Davidson B (1993) Chem Rev 93:1771

    Article  CAS  Google Scholar 

  8. Furstner A, Weintritt H, Hupperts A (1995) J Org Chem 60:6637

    Article  Google Scholar 

  9. Banwell M, Flynn B, Hamel E, Hockless D (1997) Chem Commun 2:207

    Article  Google Scholar 

  10. Boger D, Boyce C, Labroli M, Sehon C, Jin Q (1999) J Am Chem Soc 121:54

    Article  CAS  Google Scholar 

  11. Gupton J, Krumpe K, Burnham B, Webb T, Shuford J, Sikorski J (1999) Tetrahedron 55:14515

    Article  CAS  Google Scholar 

  12. Kim S, Son S, Kang H (2001) Bull Korean Chem Soc 22:1403

    CAS  Google Scholar 

  13. Burnham B, Gupton J, Krumpe K, Webb T, Shuford J, Bowers B, Warren A, Barnes C, Hall I (1998) Arch Pharm Pharm Med Chem 331:337

    Article  CAS  Google Scholar 

  14. Gupton J, Burnham B, Byrd B, Krumpe K, Stokes C, Shuford J, Winkle S, Webb T, Warren A, Barnes C, Henry J, Hall I (1999) Pharmazie 54:691

    PubMed  CAS  Google Scholar 

  15. Gupton J, Burnham B, Krumpe K, Du K, Sikorski J, Warren A, Barnes C, Hall I (2000) Arch Pharm Pharm Med Chem 333:3

    Article  CAS  Google Scholar 

  16. Evans M, Smith D, Holub J, Argenti A, Hoff M, Daiglish G, Wilson D, Taylor B, Berkowitz J, Burnham B, Krumpe K, Gupton J, Scarlett T, Durham R, Hall I (2003) Arch Pharm Pharm Med Chem 336:1

    Article  Google Scholar 

  17. Bullington J, Wolff R, Jackson P (2002) J Org Chem 67:9439

    Article  PubMed  CAS  Google Scholar 

  18. Liu J, Yang Q, Mak T, Wong H (2000) J Org Chem 65:3587

    Article  PubMed  CAS  Google Scholar 

  19. Andersen R, Faulkner J, Cun-heng H, Van Duyne G, Clardy J (1985) J Am Chem Soc 107:5492

    Article  CAS  Google Scholar 

  20. Bailly C (2004) Cur Med Chem–Anti-Cancer Agents 4:363

    Article  CAS  Google Scholar 

  21. Dias N, Vezin H, Lansiaux A, Bailly C (2005) Top Curr Chem 253:89

    CAS  Google Scholar 

  22. Marco E, Laine W, Tardy C, Lansiaux A, Iwao M, Ishibashi F, Bailly C, Gago F (2005) 48:3796

    Google Scholar 

  23. Tardy C, Facompre M, Laine W, Baldeyrou B, Gravalos D, Francesch A, Mateo C, Pastor A, Jimenez J, Manzanares I, Cuevas C, Bailly C (2004) Bioorg Med Chem 12:1697

    Article  PubMed  CAS  Google Scholar 

  24. Facompre M, Tardy C, Bal-Mahieu C, Colson P, Perez C, Manzanares I, Cuevas C, Bailly C (2003) Cancer Res 63:7392

    PubMed  CAS  Google Scholar 

  25. Reddy M, Rao M, Rhodes D, Hansen M, Rubins K, Bushman F, Venkateswarlu Y, Faulkner J (1999) J Med Chem 42:1901

    Article  PubMed  CAS  Google Scholar 

  26. Ishibashi F, Tanabe S, Oda T, Iwao M (2002) J Nat Prod 65:500

    Article  PubMed  CAS  Google Scholar 

  27. Quesada A, Gravalos M, Puentes F (1996) Brit J Cancer 74:677

    PubMed  CAS  Google Scholar 

  28. Vanhuyse M, Kluza J, Tardy C, Otero G, Cuevas C, Bailly C, Lansiaux A (2005) Cancer Lett 221:165

    Article  PubMed  CAS  Google Scholar 

  29. Heim A, Terpin A, Steglich W (1997) Angew Chem Int Ed Engl 36:155

    Article  CAS  Google Scholar 

  30. Peschko C, Winklhofer C, Steglich W (2000) Chem Eur J 6:1147

    Article  CAS  Google Scholar 

  31. Banwell M, Flynn B, Hockless D (1997) Chem Commun 23:2259

    Article  Google Scholar 

  32. Banwell M, Flynn B, Hockless D, Longmore R, Rae D (1998) Aust J Chem 52:755

    Article  Google Scholar 

  33. Ruchirawat S, Mutarapat T (2001) Tetrahedron Lett 42:1205

    Article  CAS  Google Scholar 

  34. Ploypradith P, Jinajlueng W, Pavaro C, Ruchirawat S (2003) Tetrahedron Lett 44:1363

    Article  CAS  Google Scholar 

  35. Ploypradith P, Mahidol C, Sahakitpichna P, Wongbundit S, Ruchirawat S (2004) Angew Chem Int Ed 43:866

    Article  CAS  Google Scholar 

  36. Diaz M, Guitian E, Castedo L (2001) Synlett 7:1164

    Article  Google Scholar 

  37. Iwao M, Takeuchi T, Fujikawa N, Fukuda T, Ishibashi F (2003) Tetrahedron Lett 44:4443

    Article  CAS  Google Scholar 

  38. Handy S, Zhang Y, Bregman H (2004) J Org Chem 69:2362

    Article  PubMed  CAS  Google Scholar 

  39. Handy S, Zhang Y (2005) Org Prep Proc Int 37:411

    Article  CAS  Google Scholar 

  40. Olsen C, Parera N, Albericio F, Alvarez M (2005) Tetrahedron Lett 46:2041

    Article  CAS  Google Scholar 

  41. Cironi P, Manzanares I, Albericio F, Alvarez M (2003) Org Lett 5:2959

    Article  PubMed  CAS  Google Scholar 

  42. Marfil M, Albericio F, Alvarez M (2004) Tetrahedron 60:8659

    Article  CAS  Google Scholar 

  43. Ploypradith P, Kagan R, Ruchirawat S (2005) J Org Chem 70:5119

    Article  PubMed  CAS  Google Scholar 

  44. Kang H, Fenical W (1997) J Org Chem 62:3254

    Article  PubMed  CAS  Google Scholar 

  45. Chan G, Francis T, Thureen D, Offen P, Pierce N, Westley J, Johnson R, Faulkner J (1993) J Org Chem 58:2543

    Article  Google Scholar 

  46. Boger D, Soenen D, Boyce C, Hedrick M, Jin Q (2000) J Org Chem 65:2479

    Article  PubMed  CAS  Google Scholar 

  47. Tao H, Hwang I, Boger D (2004) Bioorg Med Chem Lett 14:5979

    Article  PubMed  CAS  Google Scholar 

  48. Gupton J, Clough S, Miller R, Lukens J, Henry C, Kanters R, Sikorski J (2003) Tetrahedron 59:207

    Article  CAS  Google Scholar 

  49. Peschko C, Steglich W (2000) Tetrahedron Lett 41:9477

    Article  CAS  Google Scholar 

  50. Namsa-aid A, Ruchirawat S (2002) Org Lett 4:2633

    Article  PubMed  CAS  Google Scholar 

  51. Hamasaki A, Zimpleman J, Hwang I, Boger D (2005) J Am Chem Soc 127:10767

    Article  PubMed  CAS  Google Scholar 

  52. Rudi A, Goldberg I, Stein Z, Frolow F, Benayahu Y, Schleyer M, Kashman Y (1994) J Org Chem 59:999

    Article  CAS  Google Scholar 

  53. Loya S, Rudi A, Kashman Y, Hizi A (1999) Biochem J 344:85

    Article  PubMed  CAS  Google Scholar 

  54. Rudi A, Evan Y, Aknin M, Kashman Y (2000) J Nat Prod 63:832

    Article  PubMed  CAS  Google Scholar 

  55. Kreipl A, Reid C, Steglich W (2002) Org Lett 4:3287

    Article  PubMed  CAS  Google Scholar 

  56. Gupton J, Miller R, Krumpe K, Clough S, Banner E, Kanters R, Du K, Keertikar K, Lauerman N, Solano J, Adams B, Callahan D, Little B, Scharf A, Sikorski J (2005) Tetrahedron 61:1845

    Article  CAS  Google Scholar 

  57. Palermo J, Rodriguez B, Florencia M, Seldes A (1996) Tetrahedron 52:2727

    Article  CAS  Google Scholar 

  58. Furstner A, Krause H, Thiel O (2002) Tetrahedron 58:6373

    Article  CAS  Google Scholar 

  59. Frode R, Hinze C, Josten I, Schmidt B, Steffan B, Steglich W (1994) Tetrahedron Lett 35:1689

    Article  Google Scholar 

  60. Hoshino T, Kojima Y, Hayashi T, Uchiyama T, Kaneko K (1993) Biosci Biotech Biochem 57:775

    Article  CAS  Google Scholar 

  61. Kashman Y, Goldshlager G, Gravalos M, Schleyer M (1999) Tetrahedron Lett 40:997

    Article  CAS  Google Scholar 

  62. Heinrich M, Steglich W, Banwell M, Kashman Y (2003) Tetrahedron 59:9239

    Article  CAS  Google Scholar 

  63. Banwell M, Bray A, Edwards A, Wong D (2002) J Chem Soc Perkin Trans 1 11:1340

    Article  CAS  Google Scholar 

  64. Warabi K, Matsunaga S, van Soest R, Fusetani N (2003) J Org Chem 68:2765

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Gottwald Science Center, University of Richmond, 23173, Richmond, VA, USA

    John T. Gupton

Authors
  1. John T. Gupton
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to John T. Gupton .

Editor information

Moses Lee

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

Gupton, J.T. Pyrrole Natural Products with Antitumor Properties. In: Lee, M. (eds) Heterocyclic Antitumor Antibiotics. Topics in Heterocyclic Chemistry, vol 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_019

Download citation

Publish with us

Policies and ethics

Search

Navigation