Regioselective synthetic approaches towards 1,2,8,9-tetraazadispiro[4.1.4.2]trideca-2,9-dien-6-ones of potential antimicrobial properties

European Journal of Medicinal Chemistry

Volumn 44, Issue 6, 2009, Pages 2447-2451

  Girgis, Adel S ^a   Barsoum, Flora F ^b   Samir, Ahmed ^c  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b CAIRO UNIVERSITY   (Egypt)

^c Cairo University   (Egypt)

Author keywords

1,2,8,9 Tetraazadispiro 4.1.4.2 trideca 2,9 dien 6 ones; 1,3 Dipolar cycloaddition reactions; 2,5 Bis(arylmethylidene)cyclopentanones; Antimicrobial properties; Nitrilimines

Indexed keywords

1,3 DIPHENYL 4 (4 FLUOROPHENYL) 7 [(4 FLUOROPHENYL)METHYLIDENE] 1,2 DIAZASPIRO[4.4]NON 2 EN 6 ONE; 1,3 DIPHENYL 4 (4 METHYLPHENYL) 7 [(4 METHYLPHENYL)METHYLIDENE] 1,2 DIAZASPIRO[4.4]NON 2 EN 6 ONE; 1,3,4,8,10,11 HEXAPHENYL 1,2,8,9 TETRAAZADISPIRO[4.1.4.2]TRIDECA 2,9 DIEN 6 ONE; 1,8 BIS(4 METHYLPHENYL) 3,4,10,11 TETRAPHENYL 1,2,8,9 TETRAAZADISPIRO[4.1.4.2]TRIDECA 2,9 DIEN 6 ONE; 3,4 DIPHENYL 1 (4 METHYLPHENYL) 7 (PHENYLMETHYLIDENE) 1,2 DIAZASPIRO[4.4]NON 2 EN 6 ONE; 4,11 BIS(4 CHLOROPHENYL) 1,3,8,10 TETRAPHENYL 1,2,8,9 TETRAAZADISPIRO[4.1.4.2]TRIDECA 2,9 DIEN 6 ONE; 4,11 BIS(4 CHLOROPHENYL) 1,8 BIS(4 METHYLPHENYL) 3,10 DIPHENYL 1,2,8,9 TETRAAZADISPIRO[4.1.4.2]TRIDECA 2,9 DIEN 6 ONE; 4,11 BIS(4 FLUOROPHENYL) 1,3,8,10 TETRAPHENYL 1,2,8,9 TETRAAZADISPIRO[4.1.4.2]TRIDECA 2,9 DIEN 6 ONE; 4,11 BIS(4 FLUOROPHENYL) 1,8 BIS(4 METHYLPHENYL) 3,10 DIPHENYL 1,2,8,9 TETRAAZADISPIRO[4.1.4.2]TRIDECA 2,9 DIEN 6 ONE; 7 (PHENYLMETHYLIDENE) 1,3,4 TRIPHENYL 1,2 DIAZASPIRO[4.4]NON 2 EN 6 ON; ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; INFRARED SPECTROMETRY; KLEBSIELLA PNEUMONIAE; NONHUMAN; PROTEUS VULGARIS; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS AGALACTIAE; X RAY DIFFRACTION;

ANTI-INFECTIVE AGENTS; CANDIDA ALBICANS; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; KLEBSIELLA PNEUMONIAE; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEUS VULGARIS; PYRAZOLES; SPIRO COMPOUNDS; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STREPTOCOCCUS AGALACTIAE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 64249088346     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.01.008     Document Type: Article

References (34)

1. Daly J.W., Karle I.L., Myers C.W., Tokuyama T., Waters J.A., and Witkop B. Proc. Natl. Acad. Sci. U.S.A. 68 (1971) 1870-1875
2. Perron F., and Albizati K.F. Chem. Rev. 89 (1989) 1617-1661
3. Okita T., and Isobe M. Tetrahedron 50 (1994) 11143-11152
4. Rosenmund P., Hosseini-Merescht M., and Bub C. Liebigs Ann. Chem. (1994) 151-158
5. Kornet M.J., and Thio A.P. J. Med. Chem. 19 (1976) 892-898
6. J.J. Kulagowski, PCT Int. Appl. WO0047,562 (Cl. C07D221/20), Aug. 17, 2000;
7. Chem. Abstr. 133 (2000) 177116
8. Fisera L., Sauter F., Froehlich J., Feng Y., Ertl P., and Mereiter K. Monatsh. Chem. 125 (1994) 553-563
9. Jayashankaran J., Manian R.D.R.S., and Raghunathan R. Tetrahedron Lett. 45 (2004) 7303-7305
10. Subramaniyan G., Raghunathan R., and Castro A.M.M. Tetrahedron 59 (2003) 335-340
11. Strauss A., and Otto H.H. Helv. Chim. Acta 80 (1997) 1823-1830
12. Stverkova S., Zak Z., and Jonas J. Liebigs Ann. Chem. (1995) 477-480
13. Baba N., and Soufiaoui M. Tetrahedron Lett. 31 (1990) 1709-1712
14. Palaska E., Aytemir M., Uzbay I.T., and Erol D. Eur. J. Med. Chem. 36 (2001) 539-543
15. Parmar S.S., Pandey B.R., Dwivedi C., and Harbison R.D. J. Pharm. Sci. 63 (1974) 1152-1155
16. Soni N., Pande K., Kalsi R., Gupta T.K., Parmar S.S., and Barthwal J.P. Res. Commun. Chem. Pathol. Pharmacol. 56 (1987) 129-132
17. Jeong T.S., Kim K.S., Kim J.R., Cho K.H., Lee S., and Lee W.S. Bioorg. Med. Chem. Lett. 14 (2004) 2719-2723
18. Stirrett K.L., Ferreras J.A., Jayaprakash V., Sinha B.N., Ren T., and Quadri L.E.N. Bioorg. Med. Chem. Lett. 18 (2008) 2662-2668
19. Ali M.A., and Shaharyar M. Bioorg. Med. Chem. 15 (2007) 1896-1902
20. Ali M.A., Shaharyar M., and Siddiqui A.A. Eur. J. Med. Chem. 42 (2007) 268-275
21. Shaharyar M., Siddiqui A.A., and Ali M.A. Bioorg. Med. Chem. Lett. 16 (2006) 4571-4574
22. Bonacorso H.G., Wentz A.P., Lourega R.V., Cechinel C.A., Moraes T.S., Coelho H.S., Zanatta N., Martins M.A.P., Höerner M., and Alves S.H. J. Fluorine Chem. 127 (2006) 1066-1072
23. Girgis A.S., Ibrahim Y.A., Ahmed-Farag I.S., and Mishriky N. J. Chem. Res., Synop. (2000) 508-509
24. Fathi T., Ciamala K., Dinh An N., and Vebrel J. Can. J. Chem. 72 (1994) 1424-1428
25. Girgis A.S., Ibrahim Y.A., Mishriky N., Lisgarten J.N., Potter B.S., and Palmer R.A. Tetrahedron 57 (2001) 2015-2019
26. Girgis A.S. J. Chem. Res. (2006) 127-129
27. Clinical and Laboratory Standards Institute (Formerly NCCLS). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria Grow Aerobically. Approved Standard M7-A4 (2005), Clinical and Laboratory Standards Institute, Wayne, Pennsylvania, USA
28. Cornubert R., and De Demo M. Compt. Rend 194 (1932) 1587-1589
29. Maccioni A., and Marongiu E. Ann. Chim. (Rome) 48 (1958) 557-564
30. Hopkin S.E., Muir M., and Theocharis C.R. J. Chem. Soc. Perkin Trans. 2 (1991) 1131-1135
31. Huisgen R., Seidel M., Wallbillich G., and Kunpfer H. Tetrahedron 17 (1962) 3-29
32. Hegarty A.F., Kearney J.A., and Scott F.L. J. Chem. Soc. Perkin Trans. 2 (1973) 1422-1430
33. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., and Spagna R. J. Appl. Crystallogr. 32 (1999) 115-119
34. Mackay S., Gilmore C.J., Edwards C., Stewart N., and Shankland K. maXus Computer Program for the Solution and Refinement of Crystal Structures (1999), Bruker Nonius, MacScience, & The University of Glasgow, The Netherlands, Japan