Display options
Cite
Zaki YH, Sayed AR, Elroby SA. Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines. Chem Cent J. 2016;10:17doi: 10.1186/s13065-016-0163-2.
Zaki, Y. H., Sayed, A. R., & Elroby, S. A. (2016). Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines. Chemistry Central journal, 1017. https://doi.org/10.1186/s13065-016-0163-2
Zaki, Yasser Hassan, et al. "Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines." Chemistry Central journal vol. 10 (2016): 17. doi: https://doi.org/10.1186/s13065-016-0163-2
Zaki YH, Sayed AR, Elroby SA. Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines. Chem Cent J. 2016 Apr 01;10:17. doi: 10.1186/s13065-016-0163-2. eCollection 2016. PMID: 27042207; PMCID: PMC4818429.
Copy Download .nbib Format: NLM
Share it on

Chem Cent J. 2016 Apr 01;10:17. doi: 10.1186/s13065-016-0163-2. eCollection 2016.

Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines.

Chemistry Central journal

Yasser Hassan Zaki, Abdelwahed Rashad Sayed, Shaaban A Elroby

Affiliations

  1. Department of Chemistry , Faculty of Science, Beni-Suef University, Beni-Suef, 62514 Egypt.
  2. Department of Chemistry, Faculty of Science, KFU, Hofuf, Saudi Arabia.
  3. Department of Chemistry , Faculty of Science, Beni-Suef University, Beni-Suef, 62514 Egypt ; Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, 21589 Saudi Arabia.

PMID: 27042207 PMCID: PMC4818429 DOI: 10.1186/s13065-016-0163-2

Abstract

BACKGROUND: Isoxazoles exhibit interesting biological activities, and the 1,3-dipolar cycloaddition(13DC) reactions play an important role in both mechanistic and synthetic organic chemistry. Pyrazoles and annulated pyrazoles exhibit some diverse biological activities. They are used as antipyretic, analgesic drugs, tranquilizing, and herbicidal agents. Pyrazoles are also used extensively as useful synthons in organic synthesis. Pyrazolo[3,4-d]pyridazines showed good antimicrobial, anti-inflammatory and analgesic activities. Several oximes are found to be hyperglycemic, anti-neoplastic, anti-inflammatory, anti-leishmanial and VEGFR-2 kinase inhibitors.

RESULTS: The present work describes an efficient synthesis protocol and molecular orbital calculations of isoxazoline and pyrrolo[3,4-d]isoxazole-4,6-dione derivatives from the reaction of hydroximoyl chloride with acrylonitrile, acrylamide, and N-arylmalemides. In addition, pyrazoles and pyrazolo[3,4-d]pyridazines are obtained via the reaction of 3-(dimethylamino)-1-(2,4-dimethyl-1,3-thiazol-5-yl)prop-2-ene-1-one with hydrazonoyl halides. Pyrazolo[1,5-a]pyrimidines were derived from condensation of either Sodium Salt of 3-Hydroxy-1-(2,4-dimethylthiazol-5-yl)prop-2-en-1-one (10) or 3-(dimethylamino)-1-(2,4-dimethyl)(1,3-thiazol-5-yl)prop-2-en-1-one (11) with aiminopyrozoles. A comparative study of the biological activity of the synthesized compounds with ampicillin and tetracycline is compiled in Table 3. Generally, all synthesized compounds showed an adequate inhibitory efficiency of growth of gram-positive and gram-negative bacteria. Structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data and a computational study.

CONCLUSIONS: In summary, new and efficient synthetic routes of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-dione derivatives, pyrazoles, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines have been achieved and the biological activity has been investigated.Graphical abstractNew and efficient synthetic routes of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-dione derivatives, pyrazolo[3,4-d]pyridazines and pyrazolo [1,5-a] pyrimidines.

Keywords: 1,3-Dipolar cycloadditions; Density functional theory; Isoxazoline; Pyrazoles; Pyrazolo[1,5-a]pyrimidine; Pyrazolo[3,4-d]pyridazines; Pyrrolo[3,4-d]isoxazole; Regioselectivity

References

  1. Acta Crystallogr Sect E Struct Rep Online. 2010 Aug 21;66(Pt 9):o2374 - PubMed
  2. J Med Chem. 1977 Mar;20(3):386-93 - PubMed
  3. Molecules. 2012 Jul 12;17(7):8449-63 - PubMed
  4. Eur J Med Chem. 2011 Feb;46(2):691-703 - PubMed
  5. J Med Chem. 1971 Jun;14(6):528-32 - PubMed
  6. Bioorg Med Chem Lett. 2013 Mar 1;23(5):1306-9 - PubMed
  7. Bioorg Med Chem. 2001 Mar;9(3):715-8 - PubMed
  8. J Pharm Sci. 1974 Jan;63(1):19-23 - PubMed
  9. Food Cosmet Toxicol. 1969 Jul;7(4):287-95 - PubMed
  10. J Am Chem Soc. 2009 Jun 17;131(23):8121-33 - PubMed
  11. Org Biomol Chem. 2014 Oct 28;12(40):7993-8007 - PubMed
  12. J Phys Chem A. 2011 Dec 1;115(47):13906-20 - PubMed

Publication Types