Antibacterial evaluation of novel N-arylimino-1,2,3-dithiazoles and N-arylcyanothioformamides

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 5, 1996, Pages 529-532

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

^a UNIVERSITÉ DE LA ROCHELLE   (France)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 DITHIAZOLE DERIVATIVE; ANTIINFECTIVE AGENT; FORMAMIDE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; STRUCTURE ACTIVITY RELATION;

EID: 0029971645     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00062-5     Document Type: Article

References (14)

1. Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1995, 2097; Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1995, 1419.
2. Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1995, 2097; Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1995, 1419.
3. English, R.F., Ph. D. Thesis, University of London, 1989. Rees, C. W. J. Heterocycl. Chem. 1992, 29, 639.
4. English, R.F., Ph. D. Thesis, University of London, 1989. Rees, C. W. J. Heterocycl. Chem. 1992, 29, 639.
5. Moore, J. E. US Pat., 4 059 590/1977 (Chem. Abstr. 1978, 88, 50874).
6. Mayer, R.; Förster, E.; Matauschek, B. D. German Pat., DD 212 387/1984 (Chem. Abstr. 1985, 102, 113064).
7. Besson, T.; Rees, C. W. J. Chem. Soc., Perkin Trans 1 1995, 1659.
8. Appel, R.; Janssen, H.; Siray, M; Knoch, F. Chem. Ber. 1985, 118, 1632.
9. All compounds were prepared according methods previously described in ref. 2,3 and 6 and were fully characterised by spectroscopy and elemental analysis. N-(4-Chloro-5H-1,2,3-dithiazol-5-ylidene)aniline derivatives 2; general procedure. To a solution of the substituted aniline in dichloromethane was added 4,5-dichloro-1,2,3-dithiazolium chloride 1 (1 equiv.). The mixture was stirred at room temperature for 2 h after which pyridine (2 equiv.) was added to give a red solution. This was stirred for a further 2 h, filtered and the product isolated by flash column chromatography with light petroleum-dichloromethane as the eluent. N-(Cyanothioformyl)anilines derivatives 3; general procedure. A solution of the N-arylimine 2 and triphenylphosphine in undried dichloromethane was stirred at room temperature. The reaction was followed by TLC and when complete the product was purified by flash chromatography (eluent: light petroleum-dichloromethane) to give the title compounds.
10. Lab.coll.: Laboratory collection.
11. All the bacteria were grown on agar plates (37°C, 24 h), except S. pyogenes which was grown on 5% sheep blood agar plates.
12. Barry, A.L.; Thornsberry, C. In Susceptibility tests: Diffusion test procedures; Balows, A.; Hausler, W.J.; Herrmann, K.L.Jr.;. Isenberg, H.D.; Shadomy, H.J. (Ed.): Manual of clinical microbiology, 5th ed. American Society for Microbiology, Washington, D.C., 1991; p. 1117-1125.
13. MICs were determinated by the macrodilution broth method. 13 The tested compounds were first dissolved in DMF. The concentration of DMF was always 1% in Mueller-Hinton broth, that did not affect the growth of any of the microorganisms employed.
14. Sahm, D.F. and Washington, J.A. In Antibacterial susceptibility tests: Dilution methods; Balows, A.; Hausler, W.J.; Herrmann, K.L.Jr.; Isenberg, H.D.; Shadomy, H.J. (Ed.); Manual of clinical microbiology, 5th ed. American Society for Microbiology, Washington, D.C., 1991; p. 1105-1116.