Antimicrobial evaluation of 3,1-benzoxazin-4-ones, 3,1-benzothiazin-4-ones, 4-alkoxyquinazolin-2-carbonitriles and N-arylimino-1,2,3-dithiazoles

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 19, 1996, Pages 2343-2348

  Besson, Thierry ^a   Rees, Charles W ^b   Cottenceau, Gilles ^a   Pons, Anne Marie ^a  

^a UNIVERSITÉ DE LA ROCHELLE   (France)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4H 3,1 BENZOXAZIN 4 ONE DERIVATIVE; AMPHOTERICIN B; ANTIFUNGAL AGENT; FLUCONAZOLE; FLUCYTOSINE; QUINAZOLINE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA; CONTROLLED STUDY; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM;

EID: 0030575612     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00423-4     Document Type: Article

References (19)

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11. 8. All compounds were fully characterised by spectroscopy and elemental analysis. 4-Oxo-4H-3,1-benzoxazine-2-carbonitrile derivatives 4 and 4-oxo-4H-benzo-3,1-thiazine-2-carbonitrile derivatives 5 were prepared from N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-anthranilic acid according methods previously described in ref. 2-6. 4-Substituted-quinazoline-2-carbonitriles (e.g. 6 and 7). General procedure from imines 2. (a) Conventional heating: a stirred mixture of nitriles 2b and 2g (1 mmol) and sodium hydride (NaH, 1 mmol) in the alcohol (5 ml) was heated at reflux for 40 h. The product was purified by column chromatography. (b) Microwave experiments: the reaction mixture was placed in microwave oven (Synthewave S402 Prolabo® microwave reactor (monomode system) which has a quartz reactor, variable speed rotation, visual control, irradiation monitored by PC computer, infrared measurement and continuous feedback temperature control by PC) in an open vessel. The irradiation was programmed for 2 h with a delay of 10-15 seconds to obtain reflux. The product was purified as described above.
12. 9. Lab.coll: Laboratory collection; ATCC: American Type Culture Collection; DSM: Deutsche Sammlung von Mikroorganismen,und Zellkulturen GmbH; CIP: Collection Institut Pasteur.
13. 10. All the bacteria were grown on nutrient agar plates (35 °C, 24 h), except S. pyogenes which was grown on 5% sheep blood agar plates.
14. 11 The tested compounds were first dissolved in DMF. The concentration of DMF was always 1% in the Mueller-Hinton broth, which did not affect the growth of any of the bacteria employed.
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16. 13. Yeasts were grown on Sabouraud dextrose agar plates (37° C, 24 h).
17. 14. The tested compounds were first dissolved in DMF. The concentration of DMF was always 1% in RPMI 1640 (with L-glutamine) buffered to pH 7.0 with 0.165 M MOPS buffer which did not affect the growth of any of the yeasts employed.
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