Synthesis and antibacterial activity of new spiro[thiadiazoline-(pyrazolo[3,4-d]pyrimidine)] derivatives

Journal of Chemistry

Volumn 2015, Issue , 2015, Pages

  El Fal, Mohammed ^a   Ramli, Youssef ^b   Zerzouf, Abdelfettah ^c   Talbaoui, Ahmed ^a   Bakri, Youssef ^a   Essassi, El Mokhtar ^a  

^a FACULTÉ DES SCIENCES   (Morocco)

^b MOHAMMED V UNIVERSITY   (Morocco)

^c MOHAMMED V UNIVERSITY IN RABAT   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84930653024     PISSN: 20909063     EISSN: 20909071     Source Type: Journal    
DOI: 10.1155/2015/982404     Document Type: Article

References (32)

1. P. Dinér, J. P. Alao, J. Söderlund, P. Sunnerhagen, and M. Grotli, "Preparation of 3-substituted-1-isopropyl-1 H-pyrazolo[3, 4-d]pyrimidin-4-amines as RET kinase inhibitors", Journal of Medicinal Chemistry, vol. 55, no. 10, pp. 4872-4876, 2012.
2. L. L. Yang, G. B. Li, H. X. Yan et al., "Discovery of N6-phenyl-1H-pyrazolo[3, 4-d]pyrimidine-3, 6-diamine derivatives as novel CK1 inhibitors using common-feature pharmacophore model based virtual screening and hit-to-lead optimization", European Journal of Medicinal Chemistry, vol. 56, pp. 30-38, 2012.
3. J.-H. Chern, K.-S. Shia, T.-A. Hsu et al., "Design, synthesis, and structure-activity relationships of pyrazolo[3, 4-d]pyrimidines: a novel class of potent enterovirus inhibitors", Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 10, pp. 2519-2525, 2004.
4. T. A. Bektemirov, E. V. Chekunova, I. A. Korbukh, N. Bulychev Yu, N. G. Yakunina, and M. N. Preobrazhenskaya, "Antiviral activity of substituted 6-methylmercaptopyrazolo (3, 4-d) pyrimidines and their ribosides", Acta Virologica, vol. 25, no. 5, pp. 326-329, 1981.
5. 3-Mediated human glioblastoma cell proliferation", Journal of Medicinal Chemistry, vol. 53, no. 10, pp. 3954-3963, 2010.
6. 2A-antagonistischer Wirkung", Die Pharmazie, vol. 60, no. 10, pp. 732-735, 2005.
7. S.-A. Poulsen and R. J. Quinn, "Synthesis and structure-activity relationship of pyrazolo[3, 4-d]pyrimidines: potent and selective adenosine A1 receptor antagonists", Journal of Medicinal Chemistry, vol. 39, no. 21, pp. 4156-4161, 1996.
8. C. M. Niswender, E. P. Lebois, Q. Luo et al., "Synthesis and antitubercular evaluation of some novel pyrazolo[3, 4-d]pyrimidine derivatives", Medicinal Chemistry Research, vol. 21, pp. 1887-1891, 2012.
9. B. S. Holla, M. Mahalinga, M. S. Karthikeyan, P. M. Akberali, and N. S. Shetty, "Synthesis of some novel pyrazolo[3, 4-d]pyrimidine derivatives as potential antimicrobial agents", Bioorganic and Medicinal Chemistry, vol. 14, no. 6, pp. 2040-2047, 2006.
10. D. Bhambi, V. K. Salvi, J. L. Jat, S. Ojha, and G. L. Talesara, "Synthesis and antimicrobial activity of some new indole containing isoxazolines and phthalimidoxy derivatives of thiazolidinone and thiohydantoin", Journal of Sulfur Chemistry, vol. 28, no. 2, pp. 155-163, 2007.
11. R. A. M. Fatty, A. M. Gaafar, and A. M. S. Youssef, "A simple and efficient synthesis of new substituted benzothienopyridazine spiro-derivatives of pyrazolone, pyrimidinone and diazepinone", Journal of Chemical and Pharmaceutical Research, vol. 3, pp. 222-228, 2011.
12. N. N. Gajera and M. C. Patel, "Synthesis, characterization and biological screening of new spirochromanones", Journal of Chemical and Pharmaceutical Research, vol. 4, no. 7, pp. 3377-3382, 2012.
13. B. S. Rane, S. V. Deshmukh, M. G. Ghagare, R. V. Rote, and M. N. Jachak, "Synthesis of spiro-pyrimido [4, 5-b]quinoline and study of their antimicrobial activities", Journal of Chemical and Pharmaceutical Research, vol. 4, no. 7, pp. 3562-3567, 2012.
14. J. R. Yerrabelly, V. Chakravarthula, H. Yerrabelly et al., "Unusual tandem ring closing metathesis. Claisen rearrangement enroute to spiro annulation of O-allyl biscoumarins", Tetrahedron Letters, vol. 56, no. 17, pp. 2180-2182, 2015.
15. K. De, A. Bhaumik, B. Banerjee, and C. Mukhopadhyay, "An expeditious and efficient synthesis of spiro-pyrazolo[3, 4-b]pyridines catalysed by recyclablemesoporous aluminosilicate nanoparticles in aqueous-ethanol", Tetrahedron Letters, vol. 56, no. 13, pp. 1614-1618, 2015.
16. S. Abouricha, E. M. Rakib, N. Benchat, M. Alaoui, H. Allouchi, and B. El Bali, "Facile synthesis of new spirothiadiazolopyridazines by 1, 3-dipolar cycloaddition", Synthetic Communications, vol. 35, no. 16, pp. 2213-2221, 2005.
17. E. V. Budarina, N. N. Labeish, V. K. Bel'Skii, and V. A. Galishev, "Hetrocyclic thiones and their analogs in reactions of 1, 3-dipolar addition: v. Reactions of 2, 3, 3-triphenyl-1-thioxophthalimidine with nitrile imines", Russian Journal of Organic Chemistry, vol. 41, no. 5, pp. 758-761, 2005.
18. E. M. Essassi, C. Ahoya, R. Bouhfid et al., "Synthesis and antibacterial activity of new spiro[thiadiazoline-quinoxaline] derivatives", Arkivoc, vol. 2011, no. 2, pp. 217-226, 2011.
19. K. Al Mamari, H. Ennajih, H. Zouihri, R. Bouhfid, S. W. Ng, and E. M. Essassi, "Synthesis of novel dispiro-oxindoles via 1, 3-dipolar cycloaddition reactions of azomethine ylides", Tetrahedron Letters, vol. 53, no. 18, pp. 2328-2331, 2012.
20. Y.-X. Zhang, L. Ding, X.-Y. Liu et al., "Spiro-fused Nphenylcarbazolebased host materials for blue phosphorescent organic light-emitting diodes", Organic Electronics, vol. 20, pp. 112-118, 2015.
21. P. Das, A. O. Omollo, L. J. Sitole et al., "Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents", Tetrahedron Letters, vol. 56, no. 14, pp. 1794-1797, 2015.
22. J. Naga Siva Rao and R. Raghunathan, "A facile synthesis of glyco 3-nitrochromane hybrid pyrrolidinyl spiro heterocycles via [3+2] cycloaddition of azomethine ylides", Tetrahedron Letters, vol. 56, no. 17, pp. 2276-2279, 2015.
23. M. El Fal, Y. Ramli, E. M. Essassi, M. Saadi, and L. El Ammari, "The crystal structure of 1, 5-dibenzyl-1H-pyrazolo-[3, 4-d]pyrimidine-4 (5H)-thione", Acta Crystallographica E, vol. 71, pp. o95-o96, 2015.
24. M. El Fal, Y. Ramli, E. M. Essassi, M. Saadi, and L. El Ammari, "Crystal structure of 4-allylsulfanyl-1H-pyrazolo[3, 4-d]pyrimidine", Acta Crystallographica E, vol. 70, p. o1038, 2014.
25. M. El Fal, Y. Ramli, E. M. Essassi, M. Saadi, and L. El Ammari, "Crystal structure of 1-ethylpyrazolo[3, 4-d]pyrimidine-4 (5H) - thione", Acta Crystallographica Section E: Structure Reports Online, vol. 70, no. 9, pp. o1005-o1006, 2014.
26. A. Alsubari, Y. Ramli, E. M. Essassi, and H. Zouihri, "5-(Pyridin-4-ylmeth-yl)-1Hpyrazolo-[3, 4-d]pyrimidin-4 (5H) - one", Acta Crystallographica Section E: Structure Reports Online, vol. 67, part 8, Article ID o1926, 2011.
27. M. El Fal, Y. Ramli, E. M. Essassi, M. Saadi, and L. El Ammari, "4-benzylsulfanyl-1H-pyrazolo[3, 4-d]pyrimidine", Acta Crystallographica Section E, vol. 69, no. 11, p. o1650, 2013.
28. M. El Fal, Y. Ramli, E. M. Essassi, M. Saadi, and L. El Ammari, "Crystal structure of 1-methyl-4-methylsulfanyl-1Hpyrazolo[3, 4-d]pyrimidine", Acta Crystallographica, vol. E70, Article ID o1281, 2014.
29. I. El Ouali, B. Hammouti, A. Aouniti et al., "Thermodynamic characterisation of steel corrosion in HCl in the presence of 2-phenylthieno (3, 2-b) quinoxaline", Journal of Materials and Environmental Science, vol. 1, no. 1, pp. 1-8, 2010.
30. M. Z. A. Badr, G. M. El-Naggar, H. A. H. El-Sherief, A. E. S. Abdel-Rahman, and M. F. Aly, "Reaction of quinoxaline derivatives with nucleophilic reagents", Bulletin of the Chemical Society of Japan, vol. 56, no. 1, pp. 326-330, 1983.
31. O. S. Moustafa, "Synthesis and some reactions of Quinoxalinecarboazides", Journal of the Chinese Chemical Society, vol. 47, pp. 351-357, 2000.
32. J. Sirot, Bactériologie Médicale, Flammarion, Paris, France, 2nd edition, 1990.