Synthesis and characterization of 5-substituted novel isoxazolidines derived from 1,3-dipolar cycloaddition of nitrones with olefins: Studies of antibacterial and antifungal activities

Synthetic Communications

Volumn 33, Issue 9, 2003, Pages 1545-1555

  Kumar, K R Ravi ^a   Mallesha, H ^a   Rangappa, K S ^a  

^a UNIVERSITY OF MYSORE   (India)

Author keywords

Antibacterial; Antifungal; Cycloaddition; Isoxazolidines; Nitrones

Indexed keywords

2 (4 CHLOROPHENYL) 3 (4 BIPHENYL) 5 (3 CYCLOHEXENE)ISOXAZOLIDINE DERIVATIVE; 2 (4 CHLOROPHENYL) 3 (4 BIPHENYL) 5 BENZOATE ISOXAZOLIDINE DERIVATIVE; 2 (4 CHLOROPHENYL) 3 (4 BIPHENYL) 5 CYANOISOXAZOLIDINE DERIVATIVE; 2 (4 CHLOROPHENYL) 3 (4 BIPHENYL) 5 ETHYLATE ISOXAZOLIDINE DERIVATIVE; 2 (4 CHLOROPHENYL) 3 (4 BIPHENYL) 5 METHYLENE ACETATE ISOXAZOLIDINE DERIVATIVE; 2 (4 CHLOROPHENYL) 3 (4 BIPHENYL) 5 METHYLENE HYDROXYISOXAZOLIDINE DERIVATIVE; 2 (4 CHLOROPHENYL) 3 (4 BIPHENYL) 5 METHYLISOXAZOLIDINE DERIVATIVE; 2 (4 CHLOROPHENYL) 3 (4 BIPHENYL) 5 PHENYLISOXAZOLIDINE DERIVATIVE; 2 (4 METHYLPHENYL) 3 (4 BIPHENYL) 5 (CYCLOHEXENE)ISOXAZOLIDINE DERIVATIVE; 2 (4 METHYLPHENYL) 3 (4 BIPHENYL) 5 BENZOATE ISOXAZOLIDINE DERIVATIVE; 2 (4 METHYLPHENYL) 3 (4 BIPHENYL) 5 CYANOISOXAZOLIDINE DERIVATIVE; 2 (4 METHYLPHENYL) 3 (4 BIPHENYL) 5 ETHYLATE ISOXAZOLIDINE DERIVATIVE; 2 (4 METHYLPHENYL) 3 (4 BIPHENYL) 5 METHYLATE ISOXAZOLIDINE DERIVATIVE; 2 (4 METHYLPHENYL) 3 (4 BIPHENYL) 5 METHYLENE ACETATE ISOXAZOLIDINE DERIVATIVE; 2 (4 METHYLPHENYL) 3 (4 BIPHENYL) 5 METHYLENE HYDROXYISOXAZOLIDINE DERIVATIVE; 2 (4 METHYLPHENYL) 3 (4 BIPHENYL) 5 PHENYLISOXAZOLIDINE DERIVATIVE; ALKENE; C (4 BIPHENYL) N (4 CHLOROPHENYL)NITRONE; C (4 BIPHENYL) N (4 METHYLPHENYL)NITRONE; ISOXAZOLIDINE DERIVATIVE; NITRONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; BACILLUS CEREUS; BOTRYDIPLODIA THEOBROMAE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; FUNGUS; FUSARIUM MONILIFORME; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STAPHYLOCOCCUS AUREUS;

EID: 0037628692     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120018773     Document Type: Article

References (13)

1. Black, D.St.C.; Crozier, R.F.; Davis, V.C. 1,3-Dipolar cycloaddition reactions of nitrones. Synthesis 1975, 4, 205-221.
2. Banerji, A.; Sahu, A.J. Recent advances in cycloaddition reactions of nitrones. Scient. Indus. Res. 1986, 45, 355-369.
3. Torsell, K.B.G. Nitrile Oxides, Nitrone and Nitronates in Organic Synthesis; VCH: New York, Weinheim, 1988.
4. Banerji, A.; Basu, S. Cycloaddition of C,N-diarylnitrones to 2-butenolide; synthesis of 2,3,6,6a-tetrahydrofuro[3,4-d]-isoxazol-4-(3aH)-one. Tetrahedron 1992, 48, 3335-3344.
5. Mallesha, H.; Ravikumar, K.R.; Mantelingu, K.; Rangappa, K.S. Synthesis and characterization of model ultimate carcinogens/metabolites derived from lead tetracetate oxidation of arylnitrones; 2′-deoxyguanosin adducts. Synthesis 2001, 10, 1459-1461.
6. Mallesha, H.; Ravikumar, K.R.; Rangappa, K.S. Synthesis of N-acetoxy-N-benzoyl-2-aminofluorene, an ultimate carcinogens by LTA oxidation of α-phenyl-N-(2-aminofluorenyl) nitrone, and N-(2′-deoxyguanosin-8-yl)-2-aminofluorene. Synthesis 2001, 16, 2415-2418.
7. Padwa, A.; Koehler, K.F.; Rodringuez, A. Nitrone cycloaddition. A new approach to β-lactams. J. Am. Chem. Soc. 1981, 103, 4974-4975.
8. Padwa, A.; Koehler, K.F.; Rodringuez, A. New synthesis of β-lactams based on nitrone cycloaddition to nitroalkenes. J. Org. Chem. 1984, 49, 282-288.
9. Padwa, A. 1,3-Dipolar Cycloadditon Chemistry; John Wiley and Sons: New York, 1984; Vol. 1 and 2.
10. Ochiai, M.; Obayashi, M.; Morita, K. A new 1,3-dipolar cycloaddition reaction synthesis of some isoxazolidines derivatives. Tetrahedron 1967, 23, 2641-2648.
11. Mallesh, H.; Ravikumar, K.R.; Vishukumar, B.K.; Mantelingu, K.; Rangappa, K.S. Histidine as a catalyst in organic synthesis: a facile in situ synthesis of α,N-diaryl nitrones. Proc. Indian. Acad. Sci. (Chem. Sci.). 2001, 1113 (4), 291.
12. Collins, C.H.; Lyne, P.M. Microb. Methods; Butterworth: London, 1970; 414-419.
13. Mullen, G.B.; Decory, T.R.; Mitchell, J.T.; Allen, S.D.; Kinsolving, C.R.; Gergiev, V.St. Studies on antifungal agents. Novel substituted 3,5-diphenyl-3-(1H-imidazol-1-ylmethyl)-2-alkylisoxazolidine derivatives. J. Med. Chem. 1988, 31, 2008-2014.