Reaction of naphthoquinones with substituted nitromethanes. Facile synthesis and antifungal activity of naphtho[2,3-d]isoxazole-4,9-diones

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 1, 2010, Pages 193-195

  Santos, Maria M M ^a   Faria, Natália ^b   Iley, Jim ^c   Coles, Simon J ^d   Hursthouse, Michael B ^d   Martins, M Luz ^b   Moreira, Rui ^a  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^b INSTITUTO DE HIGIENE E MEDICINA TROPICAL   (Portugal)

^c OPEN UNIVERSITY   (United Kingdom)

^d UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Antifungal agents; Heterocycles; Isoxazoles; Quinones

Indexed keywords

2 BROMO 1,4 NAPHTHOQUINONE; 2 CHLORO 3 ETHOXY 1,4 NAPHTHOQUINONE; 2,3 DICHLORO 1,4 NAPHTHOQUINONE; 2,3 DICHLORO 5,8 DIMETHOXY 1,4 NAPHTHOQUINONE; ANTIFUNGAL AGENT; ISOXAZOLE; NAPHTHO[2,3 D]ISOXAZOLE 4,9 DIONE 3 CARBOXYLATE DERIVATIVE; NAPHTHO[2,3 D]ISOXAZOLE 4,9 DIONE DERIVATIVE; NAPHTHOQUINONE; NITROMETHYL DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGAL STRAIN; NONHUMAN; X RAY CRYSTALLOGRAPHY;

ANTIFUNGAL AGENTS; CANDIDA; ISOXAZOLES; MICROBIAL SENSITIVITY TESTS; NAPHTHOQUINONES;

CANDIDA;

EID: 72049098512     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.10.137     Document Type: Article

References (20)

1. Dewick, P. M., In Medicinal Natural Products, 2nd ed., Wiley, Chichester, UK, 2002
2. Pinho e Melo T.M.V.D. Curr. Org. Chem. 9 (2005) 925
3. Kano, H.; Ogata, M.; Yukinaga, H. U.S. Patent 3,835,168, 1974.
4. Kano, H.; Ogata, M.; Yukinaga, H. U.S. Patent 3,933,828, 1976.
5. Alguacil R., Fariña F., Martín M.V., and Paredes M.C. Tetrahedron Lett. 36 (1995) 6773
6. Stevens J., Welton T., Deville J., and Behar V. Tetrahedron Lett. 44 (2003) 8901
7. Matsuura T., Bode J.W., Hachisu Y., and Suzuki K. Synlett (2003) 1746
8. Chuang C., Wu Y., and Jiang M. Tetrahedron 55 (1999) 11229
9. Snider B.B., and Che Q. Tetrahedron 58 (2002) 7821
10. Santos D., Santos M.M.M., Viana R.J.S., Castro R.E., Moreira R., and Rodrigues C.M.P. Chem. Biol. Interact. 180 (2009) 175
11. Nitromethyl derivative (2.2 mmol) and DIEA (4.4 mmol) were added to a solution of 2,3-dichloro-1,4-naphthoquinone (2.2 mmol) in EtOH (50 mL) with molecular sieves. After reflux, under argon atmosphere, the solution was filtered and evaporated to dryness. The residue was submitted to flash chromatography (n-hexane/ethyl acetate 8:2).
12. 2O (3×). The organic extract was dried and concentrated. The residue was submitted to flash chromatography (n-hexane/ethyl acetate 8:2).
13. Fieser L.F., and Brown R.H. J. Am. Chem. Soc. 71 (1949) 3609
14. 2), 127.3 (CHAr), 127.7 (CHAr), 131.1 (CAr), 131.2 (CAr), 134.2 (CHAr), 134.4 (CHAr), 141.2 (CAr), 144.7 (CAr), 168.1 (CO), 177.4 (CO), 181.1 (CO).
15. McElvain S.M., and Engelhardt E.L. J. Am. Chem. Soc. 66 (1944) 1077
16. 3), 124.4 (CAr), 136.7 (CAr), 141.6 (CAr), 153.2 (CAr), 169.0 (CO), 182.1 (CO).
17. 5S (M+1) 340.02797, found 340.02847.
18. 4 (M+1) 304.06098, found 304.06211.
19. 2 = 0.0988 [I > 2σ (I)]. Supplementary data have been deposited with the CCDC deposition number CCDC 674974.
20. 50 values were determined by probit analysis of % cell reproduction versus concentration of test compounds or ampB using the statistical analysis program provided by SPSS (Chicago, IL, USA).