Skip to main content
SpringerLink
Log in

The Chemistry of Bioactive Mesoionic Heterocycles

  • Chapter
  • First Online:
Bioactive Heterocycles VII

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 16))

Abstract

This review focuses on the latest developments in biologically interesting mesoionic compounds, such as sydnones, sydnonimines, 1,2,3,4-oxatriazolium-5-aminates, and 1,3,4-thiadiazolium-2-aminides, mainly since 2000.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Fischer E, Besthorn E (1882) Liebigs Ann Chem 212:316

    Article  Google Scholar 

  2. Bieber TI (1955) Chem Ind (London) 910

    Google Scholar 

  3. Kier LB, Roche EB (1967) J Pharm Sci 56:149

    Article  CAS  Google Scholar 

  4. Ollis WD, Ramsden CA (1976) Adv Heterocycl Chem 19:1

    Article  CAS  Google Scholar 

  5. Newton CG, Ramsden CA (1982) Tetrahedron 38:2965

    Article  CAS  Google Scholar 

  6. Azarifar D, Ghasemnejad-Bosra H (2006) Synthesis 1123

    Google Scholar 

  7. Shpak AV, Appolonova SA, Semenov VA (2005) J Chromatogr Sci 43:11

    CAS  Google Scholar 

  8. Grynberg N, Gomes R, Shinzato T, Echevarria A, Miller J (1992) Anticancer Res 12:1025

    CAS  Google Scholar 

  9. Dunkley CS, Thoman CJ (2003) Bioorg Med Chem 13:2899

    Article  CAS  Google Scholar 

  10. Halila GC, de Oliveira MB, Eshevarria A, Belem AC, Rocha ME, Carnieri EG, Martinez GR, Noleto GR, Cadena SM (2007) Chem Biol Interact 169:160

    Article  CAS  Google Scholar 

  11. Moustafa MA, Nasr MN, Gineinah MM, Bayoumi WAH (2004) Arch Pharm (Weinheim) 337:164

    Article  CAS  Google Scholar 

  12. Moustafa MA, Gineinah MM, Nasr MN, Bayoumi WAH (2004) Arch Pharm (Weinheim) 337:427

    Article  CAS  Google Scholar 

  13. Shih MH, Ke FY (2004) Bioorg Med Chem 12:4633

    Article  CAS  Google Scholar 

  14. Shih MH, Su YS, Wu CL (2007) Chem Pharm Bull 55:1126

    Article  CAS  Google Scholar 

  15. Shih MH, Tsai CH, Wang YC, Shieh MY, Lin GL, Wei CY (2007) Tetrahedron 63:2990

    Article  CAS  Google Scholar 

  16. Shih MH, Wu CL (2005) Tetrahedron 61:10917

    Article  CAS  Google Scholar 

  17. Shih MH, Yeh MY (2003) Tetrahedron 59:4103

    Article  CAS  Google Scholar 

  18. Miller MR, Megson IL (2007) Br J Pharmacol 151:305

    Article  CAS  Google Scholar 

  19. McGrowder D, Ragoobirsingh D, Brown P (2006) Int J Pharmacol 2:366

    Article  CAS  Google Scholar 

  20. Wiley JW (2007) Neurogastroenterol Motil 19:541

    Article  CAS  Google Scholar 

  21. Choi KM, Gibbons SJ, Roeder JL et al (2007) Neurogastroenterol Motil 19:585

    Article  CAS  Google Scholar 

  22. Wang PG, Xian M, Tang X, Wu X, Wen Z, Cai T, Janczuk AJ (2002) Chem Rev 102:1091

    Article  CAS  Google Scholar 

  23. Gryglewski RJ, Marcinkiewicz E, Robak J, Michalska Z, Madej J (2002) Curr Pharm Des 8:167

    Article  CAS  Google Scholar 

  24. Gasco A, Schoenafinger K (2005) The NO-releasing heterocycles. In: Wang PG, Cai TB, Taniguchi N (eds) Nitric oxide donors. Wiley-VCH, Weinheim, pp 131–175

    Chapter  Google Scholar 

  25. Herman AG, Moncada S (2005) Eur Heart J 26:1945

    Article  CAS  Google Scholar 

  26. Miller MR, Megson IL (2007) Br J Pharmacol 151:305

    Article  CAS  Google Scholar 

  27. Wang PG, Xian M, Tang X, Wu X, Wen Z, Cai T, Janczuk AJ (2002) Chem Rev 102:1091

    Article  CAS  Google Scholar 

  28. Brookes P, Walker J (1957) J Chem Soc 4409

    Google Scholar 

  29. Kankaanranta H, Knowles RG, Vuorinen P, Kosonen O, Holm P, Moilanen E (1997) Mol Pharmacol 51:882

    CAS  Google Scholar 

  30. Schrammel A, Pfeiffer S, Schmidt K, Koesling D, Mayer B (1998) Mol Pharmacol 54:207

    CAS  Google Scholar 

  31. Cai TB, Lu D, Tang X, Zhang Y, Landerholm M, Wang PG (2005) J Org Chem 70:3518

    Article  CAS  Google Scholar 

  32. Vinatier V, Soulere L, Hoffmann P (2006) Nitric Oxide 15:363

    Article  CAS  Google Scholar 

  33. Pitsikas N, Rigamonti AE, Cella SG, Sakellaridis N, Muller EE (2005) Neurobiol Aging 26:259

    Article  CAS  Google Scholar 

  34. Pitsikas N, Sakellaridis N (2007) Eur J Pharmacol 571:174

    Article  CAS  Google Scholar 

  35. Martinet W, Croons V, Timmermans JP, Herman AG, De Meyer GRY (2007) Br J Pharmacol 152:493

    Article  CAS  Google Scholar 

  36. Herman AG, Moncada S (2005) Eur Heart J 26:1945

    Article  CAS  Google Scholar 

  37. Lee CS, Kim YJ, Han ES (2007) Life Sci 80:1759

    Article  CAS  Google Scholar 

  38. Meij JTA, Haselton CL, Hillman KL, Muralikrishnan D, Ebadi M, Yu L (2004) Mol Pharmacol 66:1043

    Article  CAS  Google Scholar 

  39. Lee CS, Han ES, Park ES, Bang H (2005) Brain Res 1036:18

    Article  CAS  Google Scholar 

  40. Siegemund M, Bommel JV, Sinaasappel M, Schwarte LA, Studer W, Girard T (2007) Acta Anaesthesiol Scand 51:693

    Article  CAS  Google Scholar 

  41. Patel KP, Li YF, Hirooka Y (2001) Exp Biol Med 226:814

    CAS  Google Scholar 

  42. Schwenke DO, Pearson JT, Tsuchimochi H, Mori H, Shirai M (2005) Clin Exp Pharmacol Physiol 32:952

    Article  CAS  Google Scholar 

  43. Schwenke DO, Pearson JT, Tsuchimochi H, Kangawa K, Shirai M (2007) Clin Exp Pharmacol Physiol 34:88

    Article  CAS  Google Scholar 

  44. Bryan-Lluka LJ, Papacostas MH, Paczkowski FA, Wanstall JC (2004) Br J Pharmacol 143:63

    Article  CAS  Google Scholar 

  45. Marcos E, Adnot S, Pham MH, Nosjean A, Raffestin B, Hamon M, Eddahibi S (2003) Am J Respir Crit Care Med 168:487

    Article  Google Scholar 

  46. Luchowski P, Urbanska EM (2007) Eur J Pharmacol 563:130

    Article  CAS  Google Scholar 

  47. Rabkin SW, Klassen SS (2007) Nitric Oxide 16:339

    Article  CAS  Google Scholar 

  48. Rabkin SW (2007) Autophagy 3:347

    CAS  Google Scholar 

  49. Ferry-Dumazet H, Mamani-Matsuda M, Dupouy M, Belloc F, Thiolat D, Marit G, Arock M, Reiffers J, Mossalayi MD (2002) Leukemia 16:708

    Article  CAS  Google Scholar 

  50. Lau A, Arundine M, Sun HS, Jones M, Tymianski M (2006) J Neurosci 26:11540

    Article  CAS  Google Scholar 

  51. Hall ED, Detloff MR, Johnson K, Kupina NC (2004) J Neurotrauma 21:9

    Article  Google Scholar 

  52. Finnegan WG, Henry RA (1965) J Org Chem 30:567

    Article  CAS  Google Scholar 

  53. Masuda K, Kamiya T, Kashiwa K (1971) Chem Pharm Bull 19:559

    CAS  Google Scholar 

  54. Gryglewski RJ, Marcinkiewicz E, Robak J, Michalska Z, Madej J (2002) Curr Pharm Des 8:167

    Article  CAS  Google Scholar 

  55. Corell T, Pedersen SB, Lissau B, Moilanen E, Metsa-Ketela T, Kankaanranta H, Vuorinen P, Vapaatalo H, Rydell E, Andersson R et al. (1994) Pol J Pharmacol 46:553

    CAS  Google Scholar 

  56. Holm P, Kankaanranta H, Metsa-Ketela T, Moilanen E (1998) J Pharmacol 346:97

    CAS  Google Scholar 

  57. Kankaanranta H, Rydell E, Petersson AS, Holm P, Moilanen E, Corell T, Karup G, Vuorinen P, Pedersen SB, Wennmalm A, Metsa-Ketela T (1996) Br J Pharmacol 117:401

    CAS  Google Scholar 

  58. Kosonen O, Kankaanranta H, Vuorinen P, Moilanen E (1997) Eur J Pharmacol 337:55

    Article  CAS  Google Scholar 

  59. Kosonen O, Kankaanranta H, Lahde M, Vuorinen P, Ylitalo P, Moilanen E (1998) J Pharm Exp Ther 286:215

    CAS  Google Scholar 

  60. Kosonen O, Kankaanranta H, Malo-Ranta U, Ristimaki A, Moilanen E (1998) Br J Pharmacol 125:247

    Article  CAS  Google Scholar 

  61. Laursen BE, Stankevicius E, Pilegaard H, Mulvany M, Simonsen U (2006) Cardiovasc Drug Rev 24:247

    Article  CAS  Google Scholar 

  62. Gryglewski RJ, Marcinkiewicz E, Robak J, Michalska Z, Madej J (2002) Curr Pharm Des 8:167

    Article  CAS  Google Scholar 

  63. Vilpo JA, Vilpo LM, Vuorinen P, Moilanen E, Metsa-Ketela T (1997) Anticancer Drug Des 12:75

    CAS  Google Scholar 

  64. Lahteenmaki T, Sievi E, Vapaatalo H (1998) Br J Pharmacol 125:402

    Article  CAS  Google Scholar 

  65. Pacher P, Beckman JS, Liaudet L (2007) Physiol Rev 87:315

    Article  CAS  Google Scholar 

  66. Taylor EL, Rossi AG, Shaw CA, Dal Rio FP, Haslett C, Megson IL (2004) Br J Pharmacol 143:179

    Article  CAS  Google Scholar 

  67. Taylor EL, Li JT, Tupper JC, Rossi AG, Winn RK, Harlan JM (2007) Biochem Pharmacol 74:1039

    Article  CAS  Google Scholar 

  68. Wang JP (2003) Eur J Pharmacol 458:243

    Article  CAS  Google Scholar 

  69. Hsu MF, Chen YS, Huang LJ, Tsao LT, Kuo SC, Wang JP (2006) Eur J Pharmacol 535:43

    Article  CAS  Google Scholar 

  70. Kojima S, Uchida K, Sasaki K, Sunagawa M, Ohno Y, Kamikawa Y (2006) Eur J Pharmacol 550:162

    Article  CAS  Google Scholar 

  71. Sitmo M, Rehn M, Diener M (2007) Am J Physiol Gastrointest Liver Physiol 293:G886

    Article  CAS  Google Scholar 

  72. Grynberg N, Santos AC, Echevarria A (1997) Anticancer Drugs 8:88

    Article  CAS  Google Scholar 

  73. Senff-Ribeiro A, Echevarria A, Silva EF, Sanches Veiga SS, Oliveira MBM (2003) Melanoma Res 13:465

    Article  CAS  Google Scholar 

  74. Senff-Ribeiro A, Echevarria A, Silva EF, Franco CRC, Veiga SS, Oliveira MBM (2004) Br J Cancer 91:297

    CAS  Google Scholar 

  75. Senff-Ribeiro A, Echevarria A, Silva EF, Veiga SS, Oliveira MB (2004) Anticancer Drugs 15:269

    Article  CAS  Google Scholar 

  76. Cadena SMSC, Carnieri EGS, Echevarria A, De Oliveira MBM (1998) FEBS Lett 440:46

    Article  CAS  Google Scholar 

  77. Cadena SMSC, Carnieri EGS, Echevarria A, De Oliveira MBM (2002) Cell Biochem Function 20:31

    Article  CAS  Google Scholar 

  78. Cardoso JC, Cadena SMSC, Zampronio A, Arruda AMS, Carnieri EGS, Echevarria A, Constantin J, Bracht A, Oliveira MBM (2004) Drug Dev Res 61:207

    Article  CAS  Google Scholar 

  79. da Silva EF, Canto-Cavalheiro MM, Braz VR, Cysne-Finkelstein LL, Leonor L, Echevarria A (2002) Eur J Med Chem 37:979

    Article  Google Scholar 

  80. Rodrigues RF, da Silva EF, Echevarria A, Fajardo-Bonin R, Amaral VF, Leon LL, Canto-Cavalheiro MM (2007) Eur J Med Chem 42:1039

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama-shi, Ehime 790-8578, Japan

    Masami Kawase

  2. Meikai University School of Dentistry, 1-1 Keyakidai, Sakado, Saitama 350-0238, Japan

    Hiroshi Sakagami

  3. Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

    Noboru Motohashi

Authors
  1. Masami Kawase
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hiroshi Sakagami
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Noboru Motohashi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Masami Kawase .

Editor information

Noboru Motohashi

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Kawase, M., Sakagami, H., Motohashi, N. (2007). The Chemistry of Bioactive Mesoionic Heterocycles. In: Motohashi, N. (eds) Bioactive Heterocycles VII. Topics in Heterocyclic Chemistry, vol 16. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_096

Download citation

Publish with us

Policies and ethics

Search

Navigation