1,2,4-Triazolo mercapto and aminonitriles as potent antifungal agents

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 15, 2003, Pages 2601-2605

  Collin, Xavier ^a   Sauleau, Armelle ^a   Coulon, Joël ^b  

^a School of Pharmacy   (France)

^b Laboratoire de Chimie Physique et Microbiologie pour l'Environnement   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; NITRILE; THIOL DERIVATIVE; TRIAZOLE DERIVATIVE;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CANDIDA TROPICALIS; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; MICROBIOLOGICAL EXAMINATION; NONHUMAN; SACCHAROMYCES CEREVISIAE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CANDIDA; CANDIDA ALBICANS; CANDIDA TROPICALIS;

EID: 0038309147     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00378-0     Document Type: Article

References (20)

1. Heindel N.D., Reid J.R. J. Heterocycl. Chem. 17:1980;1087.
2. Holla B.S., Kalluraya B., Sridhar K.R., Drake E., Thomas L.M., Bhandary K.K., Levine M.J. Eur. J. Med. Chem. 29:1994;301.
3. Ghannoum M.A., Eweiss N.F., Bahajaj A.A., Qureshi M.A. Microbios. 37:1983;151.
4. Demirayak S., Benkli K., Güven K. Eur. J. Med. Chem. 35:2000;1037.
5. Rabodinirina M., Piens M.A., Monier M.F., Guého E., Fiere D., Mojon M. Eur. J. Clin. Microbiol. Infect. Dis. 13:1994;152.
6. Hood S., Denning D.W. J. Antimicrob. Chemother. 37:1996;71.
7. Alexander B.D. Perfect Drugs. 54:1997;657.
8. Sauleau A., Sauleau J. Phosphorus, Sulfur Silicon. 167:2000;219.
9. Reid J.R., Heindel N.D. J. Heterocycl. Chem. 13:1976;925.
10. Martin M.V. J. Antimicrob. Chemother. 44:1999;429.
11. Robert-Dernuet S. Antibiotiques et Antibiogrammes. 1995;322.
12. Beuchet P., Dherbomez M., Elkiel G., Charles G., Letourneux Y. Bioorg. Med. Chem. Lett. 9:1999;1599.
13. 3); 27.8 (d, J=54 Hz, CH); 120.1, (m, CN); 126.4 (t, J=7 Hz i-Ph); 127.8 (dt, J=162 Hz, 6.5 Hz, o-Ph); 128.5 (dd, J=160 Hz, 7 Hz, m-Ph); 129.8 (dt, J=161 Hz, 7 Hz, p-Ph); 150.3 (d, J=3 Hz, C-Ph); 154.4 (s, C-S).
14. 2); 109.9 (t, J=8 Hz, C-CN); 118.7 (m, CN); 126.7 (t, J=7 Hz, i-Ph); 127.7 (dt, J=163 Hz and 5 Hz, o-Ph);128.4 (dd, J=161 Hz and 7 Hz, m-Ph); 129.6 (dt, J=161 Hz and 7 Hz, p-Ph); 129.9 (dd, J=165 Hz and 5 Hz, m-Ph-CN); 132.2 (dd, J=168 Hz and 6 Hz, o-Ph-CN); 143.8 (m, p-Ph-CN); 152.7 (t, C-Ph);154.2, (s, C-S).
15. 6): 125.0 (dd, J=166 Hz and 6 Hz); 126.1 (t, i-Ph); 127.9 (d, J=163 Hz, o-Ph); 128.5 (dd, 161 Hz and 6 Hz, m-Ph); 129.8 (dd, J=165 Hz and 7 Hz); 130.1 (dt, J=162 Hz and 8 Hz, p-Ph); 130.9 (dt, J=162 Hz and 8 Hz, p-Ph tetrazole); 132.9 (t, J=7 Hz, i-Ph tétrazole); 146.3 (s C-Ph); 149.7 (s, C-S); 154.8 (s, S-C(=N)-N).
16. 2); 7.90 (s, 1H, NH amide); 8.00 (m, 2H, o-Ph).
17. 2); 6.95 (s, 1H NH amide); 7.45 (s, 1H, NH amide); 7.55 (m, 3H, m- and p-Ph); 8.00 (m, 2H, o-Ph).
18. 2); 109.6 (dm, J=174 Hz and 4 Hz, ββ′ pyrrole); 117.1 (t, J=8 Hz, CN); 122.0 (dm, J=194 Hz and 4 Hz, αα′ pyrrole); 124.5 (t, J=8.5 Hz, i-Ph); 126.2 (dt, J=162 Hz and 7 Hz, o-Ph); 128.9 (dd, J=163 Hz and 7 Hz, m-Ph); 130.8 (dt, J=163 Hz and 7 Hz, p-Ph); 150.2 (t, J=5.5 Hz, C-Ph); 153.4 (t, J=3.6 Hz, C-S).
19. 2).
20. 2); 7.60 (d, 2H, m-Ph); 8.04 (d, 2H, o-Ph).