Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2014, Article ID 217596, 15 pages
http://dx.doi.org/10.1155/2014/217596
Review Article

Fused Imidazopyrazoles: Synthetic Strategies and Medicinal Applications

1Chemical Industries Division, National Research Centre, Dokki, Giza 12622, Egypt
2Chemistry Department, Faculty of Science, Jazan University, Saudi Arabia
3Applied Organic Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt
4Chemistry Department, Faculty of Science, Shaqra University, Al Dawadmi, Saudi Arabia
5Chemical Engineering Department, King Saud University, P.O. Box 800, Riyadh 11421, Saudi Arabia

Received 7 June 2014; Accepted 18 July 2014; Published 14 August 2014

Academic Editor: Liviu Mitu

Copyright © 2014 Rizk E. Khidre et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. Ganapathi and A. Krishan, “Effect of 2,3-dihydro-1H-imidazo[1,2-b]pyrazole on the proliferation of mouse leukemic and normal cells in vivo,” Cancer Research, vol. 40, no. 4, pp. 1103–1108, 1980. View at Google Scholar · View at Scopus
  2. L. M. Allen and J. T. Thornthwaite, “Studies on the pharmacology and cytokinetics of 2,3-dihydro-1H-imadazo[1,2-b]pyrazole (NSC 51143) with P815 mastocytoma cells,” Cancer Research, vol. 40, no. 11, pp. 4059–4063, 1980. View at Google Scholar · View at Scopus
  3. M. C. Henry, C. D. Port, E. Rosen, and B. S. Levine, “Preclinical toxicologic study of 2,3-dihydro-1H-imidazo[1,2-b] pyrazole (IMPY) in mice, dogs, and monkeys,” Cancer Treatment Reports, vol. 64, no. 10-11, pp. 1031–1038, 1980. View at Google Scholar · View at Scopus
  4. D. D. Shoemaker, O. C. Ayers, M. E. D'Anna, and R. L. Cysyk, “Studies on the disposition of 2,3-dihydro-1H-imidazo[1,2-b]pyrazole in rodents,” European Journal of Cancer and Clinical Oncology, vol. 17, no. 4, pp. 391–396, 1981. View at Google Scholar · View at Scopus
  5. H. L. Ennis, L. Möller, J. J. Wang, and O. S. Selawry, “2,3-Dihydro-1H-imidazo[1,2-b]pyrazole. A new inhibitor of deoxyribonucleic acid synthesis,” Biochemical Pharmacology, vol. 20, no. 10, pp. 2639–2646, 1971. View at Publisher · View at Google Scholar · View at Scopus
  6. M. T. Ahmet, K. T. Douglas, J. Silver, A. J. Goddard, and D. E. Wilman, “Iron and haem complexation studies of 2,3-dihydro-1H-imidazo(1,2-b)pyrazole (IMPY, NSC 51143), a tumor cell ribonucleotide reductase inhibitor,” Anti-Cancer Drug Design, vol. 1, no. 3, pp. 189–195, 1986. View at Google Scholar · View at Scopus
  7. A. J. Goddard, R. M. Orr, J. A. Stock, and D. E. V. Wilman, “Synthesis and ribonucleotide reductase inhibitory activity of analogues of 2,3-dihydro-1H-imidazo[1,2-b]pyrazole (IMPY),” Anti-Cancer Drug Design, vol. 2, no. 3, pp. 235–245, 1987. View at Google Scholar · View at Scopus
  8. A. Krishan, K. D. Paika, and E. Frei III, “Cell cycle synchronization of human lymphoid cells in vitro by 2,3 dihydro 1H imidazo[1,2 b]pyrazole,” Cancer Research, vol. 36, no. 1, pp. 138–142, 1976. View at Google Scholar · View at Scopus
  9. A. L. Sagone Jr., J. A. Neidhart, and R. M. Husney, “Effect of 2,3-dihydro-1H-imidazo[1,2-b]pyrazole (IMPY) on the metabolism of human red cells,” Investigational New Drugs, vol. 1, no. 3, pp. 243–248, 1983. View at Google Scholar · View at Scopus
  10. A. Sato, J. A. Montgomery, and J. G. Cory, “Synergistic inhibition of leukemia L1210 cell growth in vitro by combinations of 2-fluoroadenine nucleosides and hydroxyurea or 2,3-dihydro-1H-pyrazole[2,3-a]imidazole,” Cancer Research, vol. 44, no. 8, pp. 3286–3290, 1984. View at Google Scholar · View at Scopus
  11. C. L. Vogel, J. M. Denefrio, D. C. Padgett, and M. A. Silverman, “Phase I clinical trial of weekly iv 2,3-dihydro-1H-imidazo[1,2-b]pyrazole (IMPY),” Cancer Treatment Reports, vol. 64, no. 10-11, pp. R1153–R1156, 1980. View at Google Scholar · View at Scopus
  12. J. C. Pelling and C. Shipman Jr., “Antiviral activity of 2,3-dihydro-1H-imidazo[1,2-b]pyrazole in herpes simplex virus type 1-infected mammalian cells,” Biochemical Pharmacology, vol. 25, no. 21, pp. 2377–2382, 1976. View at Publisher · View at Google Scholar · View at Scopus
  13. H. Yamanaka, Y. Ogawa, and K. Itane, “Preparation of cephem derivatives as antibacterials,” JP 05213971, 1993, http://worldwide.espacenet.com/singleLineSearch?locale=en_EP. View at Google Scholar
  14. K. Sakane, K. Kawabata, and Y. Inamoto, “Preparation of new cephem compounds,” EP 427248, 1991, http://worldwide.espacenet.com/numberSearch?locale=en_EP.
  15. H. Yamanaka, Y. Ogawa, and K. Itane, “Preparation of cephem derivatives as antibacterials,” JP 05213971, 1993, http://worldwide.espacenet.com/numberSearch?locale=en_EP.
  16. K. Sato, T. Kawagishi, and H. Kobayashi, “Silver halide color photographic material,” Tech. Rep. JP 07134380, 1995, http://worldwide.espacenet.com/numberSearch ?locale=en_EP. View at Google Scholar
  17. J. Bailey and D. N. Rogers, “Photographic color couplers, photographic materials containing them and method of forming dye images,” WO 8602467, 1986, http://worldwide.espacenet.com/numberSearch?locale=en_EP.
  18. T. Ukai, T. Ito, T. Kawagishi, and H. Takei, “Photosensitive materials containing dyes,” JP 60213937, 1985, http://worldwide.espacenet.com/numberSearch?locale=en_EP.
  19. T. Sato, T. Kawagishi, and N. Furutachi, “Producing magenta images in silver halide color photographic materials,” EP 119741, 1984, http://worldwide.espacenet.com/numberSearch?locale=en_EP.
  20. B. F. Abdel-Wahab and R. E. Khidre, “2-Chloroquinoline-3-carbaldehyde II: synthesis, reactions, and applications,” Journal of Chemistry, vol. 2013, Article ID 851297, 13 pages, 2013. View at Publisher · View at Google Scholar
  21. R. E. Khidre and B. F. Abdel-Wahab, “Application of benzoylaceteonitrile in the synthesis of pyridines derivatives,” Current Organic Chemistry, vol. 17, no. 4, pp. 430–445, 2013. View at Publisher · View at Google Scholar · View at Scopus
  22. W. M. Abdou and R. E. Khidre, “Overview of the chemical reactivity of phosphonyl carbanions toward some carbon-nitrogen systems,” Current Organic Chemistry, vol. 16, no. 7, pp. 913–930, 2012. View at Publisher · View at Google Scholar · View at Scopus
  23. B. F. Abdel-Wahab, M. F. El-Mansy, and R. E. Khidre, “Production of pyrans , pyridazines , pyrimidines , pyrazines and triazine compounds using benzoylacetonitriles as a precursor,” Journal of the Iranian Chemical Society, vol. 10, no. 6, pp. 1085–1102, 2013. View at Publisher · View at Google Scholar
  24. R. E. Khidre and B. F. Abdel-Wahab, “Synthesis of 5-membered heterocycles using benzoylacetonitriles as synthon,” Turkish Journal of Chemistry, vol. 37, no. 5, pp. 1–27, 2013. View at Google Scholar
  25. R. E. Khidre, H. A. Mohamed, and B. F. Abdel-Wahab, “Advances in the chemistry of pyrazolopyrazoles,” Turkish Journal of Chemistry, vol. 37, no. 1, pp. 1–35, 2013. View at Publisher · View at Google Scholar · View at Scopus
  26. C. Brullo, S. Spisani, R. Selvatici, and O. Bruno, “N-Aryl-2-phenyl-2,3-dihydro-imidazo[1,2-b]pyrazole-1-carboxamides 7-substituted strongly inhibiting both fMLP-OMe- and IL-8-induced human neutrophil chemotaxis,” European Journal of Medicinal Chemistry, vol. 47, no. 1, pp. 573–579, 2012. View at Publisher · View at Google Scholar · View at Scopus
  27. O. Bruno, C. Brullo, F. Bondavalli et al., “2-Phenyl-2,3-dihydro-1H-imidazo[1,2-b]pyrazole derivatives: New potent inhibitors of fMLP-induced neutrophil chemotaxis,” Bioorganic and Medicinal Chemistry Letters, vol. 17, no. 13, pp. 3696–3701, 2007. View at Publisher · View at Google Scholar · View at Scopus
  28. P. Seneci, M. Nicola, M. Inglesi, E. Vanotti, and G. Resnati, “Synthesis of mono- and disubstituted 1H-imidazo[1,2-b]pyrazoles,” Synthetic Communications, vol. 29, no. 2, pp. 311–341, 1999. View at Publisher · View at Google Scholar · View at Scopus
  29. E. Vanotti, F. Fiorentini, and M. Villa, “Synthesis of novel derivatives of 1H-imidazo[1,2-b]pyrazole as potential CNS-agents,” Journal of Heterocyclic Chemistry, vol. 31, no. 4, pp. 737–743, 1994. View at Publisher · View at Google Scholar · View at Scopus
  30. C. Parkanyi, A. O. Abdelhamid, J. C. S. Cheng, and A. S. Shawali, “Convenient synthesis of fused heterocycles from a-keto hydroximoyl chlorides and heterocyclic amines,” Journal of Heterocyclic Chemistry, vol. 21, no. 4, pp. 1029–1032, 1984. View at Publisher · View at Google Scholar
  31. H. Ohki, K. Kawabata, Y. Inamoto, S. Okuda, T. Kamimura, and K. Sakane, “Studies on 3'-quaternary ammonium cephalosporins-III. Synthesis and antibacterial activity of 3'-(3-aminopyrazolium)cephalosporins,” Bioorganic and Medicinal Chemistry, vol. 5, no. 3, pp. 557–567, 1997. View at Publisher · View at Google Scholar · View at Scopus
  32. A. O. Abdelhamid, E. K. A. Abdelall, and Y. H. Zakic, “Reactions with hydrazonoyl halides 62: synthesis and antimicrobial evaluation of some new imidazo [1,2-a]pyrimidine, imidazo [1,2-a]pyridine, imdazo [1,2-b]pyrazole, and quinoxaline derivatives,” Journal of Heterocyclic Chemistry, vol. 47, no. 2, pp. 477–482, 2010. View at Publisher · View at Google Scholar · View at Scopus
  33. A. M. Farag and K. M. Dawood, “One-pot synthesis of imidazo [1,2-b]pyrazole, imidazo[1,2-b]-1,2,4-triazole, imidazo[1,2-a]-pyridine, imidazo[1,2-a]pyrimidine, imidazo-[1,2-a]benzimidazole, and 1,2,4-triazolo-[4,3-a]benzimidazole derivatives,” Heteroatom Chemistry, vol. 8, no. 2, pp. 129–133, 1997. View at Publisher · View at Google Scholar · View at Scopus
  34. A. S. Shawali, M. Sami, S. M. Sherif, and C. Parkanyi, “Synthesis of some derivatives of imidazo[1,2-a]pyridine, pyrazolo[1,5-b]imidazole, and 4-(3H)quinazolinone from α-ketohydrazidoyl bromides,” Journal of Heterocyclic Chemistry, vol. 17, no. 5, pp. 877–880, 1980. View at Publisher · View at Google Scholar · View at Scopus
  35. J. Zhang, R. Singh, D. Goff, and T. Kinoshita, “1H- Imidazo[ 1,2-b]pyrazole-7-carbonitrile derivatives as spleen tyrosine kinase (syk) inhibitors and their preparation and use for the treatment of syk-mediated diseases,” U.S. Pat. Appl. Publ., US 20100316649 A1 20101216, 2010.
  36. A. Rahmati, M. Eskandari-Vashareh, and M. Alizadeh-Kouzehrash, “Synthesis of 3-(benzylideneamino)-2-phenyl-5H-imidazo[1,2-b]pyrazole-7- carbonitriles via a four-component condensation reaction,” Tetrahedron, vol. 69, no. 21, pp. 4199–4204, 2013. View at Publisher · View at Google Scholar · View at Scopus
  37. A. Rahmati and M. A. Kouzehrash, “Synthesis of N-alkyl-2-aryl-5 H-imidazo[1,2-b]pyrazol-3-amines by a three-component condensation reaction,” Synthesis, no. 18, Article ID N49511SS, pp. 2913–2920, 2011. View at Publisher · View at Google Scholar · View at Scopus
  38. A. O. Abdelhamid, S. S. Ghabrial, M. Y. Zaki, and N. A. Ramadan, “Facile synthesis of fused heterocycles through 2-bromobenzofurylglyoxal-2-arylhydrazones,” Archiv der Pharmazie, vol. 325, no. 4, pp. 205–209, 1992. View at Publisher · View at Google Scholar · View at Scopus
  39. P. Langer, J. Wuckelt, M. Döring, P. R. Schreiner, and H. Görls, “Regioselective anionic [3+2] cyclizations of isoxazole, pyrazole and 1,2,4-triazole dinucleophiles—efficient synthesis of 2,4-dihydroimidazo-[4,5-b]quinoxalines, 3H-imidazo[1,2-b]pyrazoles and 5H-imidazo[2,1-c]-[1,2,4]triazoles,” European Journal of Organic Chemistry, no. 12, pp. 2257–2263, 2001. View at Google Scholar · View at Scopus
  40. K.-J. Lee, H.-T. Kwon, and B.-G. Kim, “Synthesis of pyrazolo-fused heterocycles by a tandem Appel's dehydration/electrocyclization methodology,” Journal of Heterocyclic Chemistry, vol. 34, no. 6, pp. 1795–1799, 1997. View at Publisher · View at Google Scholar · View at Scopus
  41. K. Lee, D. Kim, and B. Kim, “Synthesis of pyrazole-fused heterocycles by thermal rearrangement of N-aziridinylimino ketenimines,” Journal of Heterocyclic Chemistry, vol. 40, no. 2, pp. 363–367, 2003. View at Publisher · View at Google Scholar · View at Scopus
  42. M. A. Barsy and E. A. El-Rady, “Intermolecular aza-Wittig reaction: one-step synthesis of pyrazolo[1,5-a]pyrimidine and imidazo[1,2-b]pyrazole derivatives,” Journal of Heterocyclic Chemistry, vol. 43, no. 3, pp. 523–526, 2006. View at Publisher · View at Google Scholar · View at Scopus
  43. M. Li, G. Zhao, L. Wen, W. Cao, S. Zhang, and H. Yang, “Utilization of hypervalent iodine in organic synthesis: a novel and facile two-step protocol for the synthesis of new derivatives of 1H-imidazo[1,2-b] pyrazole by the cyclocondensation involving α-tosyloxyacetophenones,” Journal of Heterocyclic Chemistry, vol. 42, no. 2, pp. 209–215, 2005. View at Publisher · View at Google Scholar · View at Scopus
  44. L. Ming, Z. Guilong, W. Lirong, and Y. Huazheng, “Hypervalent iodine in synthesis: a novel two-step procedure for the synthesis of new derivatives of 1H-imidazo[1,2-b]-pyrazole by the cyclocondensation between 5-amino-4-cyano-3-phenyl-1H-pyrazole and alpha-tosyloxyacetophenones or α-haloacetophenones,” Synthetic Communications, vol. 35, no. 4, pp. 493–501, 2005. View at Publisher · View at Google Scholar · View at Scopus
  45. A. G. A. Elagamey, S. Z. A. Sowellim, and M. N. Khodeir, “Reactions with heterocyclic amidines (V). Synthesis of some new imidazo[1,2-b] pyrazole, pyrazolo [5,1-c]-1,2,4-triazine and pyrazolo [5,1-c]-1,2,4-triazole derivatives,” Archives of Pharmacal Research, vol. 10, no. 1, pp. 14–17, 1987. View at Publisher · View at Google Scholar · View at Scopus
  46. T. Sato and M. Matsuoka, “Preparation of 1H-imidazo[1,2-b] pyrazole derivatives,” JP 07278455 A 19951024, 1995.
  47. M. H. Elnagdi, E. A. A. Hafez, H. A. El-Fahham, and E. M. Kandeel, “Reactions with heterocyclic amidines. VIII. Synthesis of some new imidazo [1,2-b] pyrazole derivatives,” Journal of Heterocyclic Chemistry, vol. 17, no. 1, pp. 73–76, 1980. View at Publisher · View at Google Scholar
  48. I. Lantos, H. Oh, C. Razgaitis, and B. Loev, “Synthesis of 6-substituted-2,3-dihydro-1H-imidazo[1,5-b]pyrazoles,” Journal of Organic Chemistry, vol. 43, no. 25, pp. 4841–4844, 1978. View at Publisher · View at Google Scholar · View at Scopus
  49. K. Liubchak, A. Tolmachev, and K. Nazarenko, “Synthesis of imidazo[4,5-c]pyrazoles via copper-catalyzed amidine cyclization,” The Journal of Organic Chemistry, vol. 77, no. 7, pp. 3365–3372, 2012. View at Publisher · View at Google Scholar · View at Scopus
  50. C. B. Vicentini, M. Manfrini, M. Mazzanti, A. Scatturin, C. Romagnoli, and D. Mares, “Synthesis of a novel series of imidazo[4,5-c]pyrazole derivatives and their evaluation as herbicidal agents,” Archiv der Pharmazie, vol. 332, no. 10, pp. 337–342, 1999. View at Google Scholar
  51. C. B. Vicentini, A. C. Veronese, P. Giori, B. Lumachi, and M. Guarneri, “A new general and efficient synthesis of imidazo[4,5-c]pyrazole derivatives,” Tetrahedron, vol. 46, no. 16, pp. 5777–5788, 1990. View at Publisher · View at Google Scholar · View at Scopus
  52. K. Pilgram, “Synthesis of 2,3-dihydro-1H-imidazo[1,2-b]pyrazoles,” Journal of Heterocyclic Chemistry, vol. 17, no. 7, pp. 1413–1416, 1980. View at Publisher · View at Google Scholar · View at Scopus
  53. J. G. Michels and G. C. Wright, “2,3-Dihydro-1H-imidazo[1,5-b]pyrazole-4,6(3aH,5H)-dione,” The Journal of Organic Chemistry, vol. 34, no. 10, pp. 3213–3215, 1969. View at Publisher · View at Google Scholar · View at Scopus
  54. T.-C. Chien, D. A. Berry, J. C. Drach, and L. B. Townsend, “Synthesis of 3-aminoimidazo[4,5-c]pyrazole nucleoside via the N-N bond formation strategy as a [5:5] fused analog of adenosine,” Nucleosides, Nucleotides and Nucleic Acids, vol. 24, no. 10–12, pp. 1971–1996, 2005. View at Publisher · View at Google Scholar · View at Scopus
  55. S. Hauptmann, H. Wilde, and M. Szymanowski, “Synthesis and dye formation from benzo [1,2-b:5,4-b′] bis (1H-imidazo[1,2-b] pyrazoles),” Zeitschrift für Chemie, vol. 28, no. 12, pp. 441–442, 1988. View at Google Scholar
  56. R. N. Butler, D. M. Colleran, D. F. O'Shea, D. Cunningham, P. McArdle, and A. M. Gilian, “New entry to the imidazo[4,5-c]pyrazole system through photochemically induced sequential transformations of substituted pyrrolo[2,3-d]-1,2,3-triazoles: X-ray crystal structure of a substituted 1,3a,6,6a-tetrahydro- imidazo[4,5-c]pyrazole,” Journal of the Chemical Society, Perkin Transactions 1, no. 22, pp. 2757–2759, 1993. View at Google Scholar · View at Scopus