Optically active antifungal azoles. VIII synthesis and antifungal activity of 1-[(1R,2R)-2-(2,4-difluoro- and 2-fluorophenyl)-2-hydroxy-1- methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-substituted phenyl)2(1H,3H)- imidazolones and 2-imidazolidinones

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 3, 1999, Pages 351-359

  Kitazaki, Tomoyuki ^a   Tasaka, Akihiro ^a   Tamura, Norikazu ^a   Matsushita, Yoshihiro ^a   Hosono, Hiroshi ^a   Hayashi, Ryogo ^a   Okonogi, Kenji ^a   Itoh, Katsumi ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

1,2,3 trisubstituted 2 butanol; Antifungal activity; Imidazolidinone; Imidazolone; Optically active antifungal azoles; Stereocontrolled synthesis

Indexed keywords

1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 1 METHYL 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 3 (4 TRIFLUOROMETHYLPHENYL) 2 IMIDAZOLIDINONE; 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 1 METHYL 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 3 (4 TRIFLUOROMETHYLPHENYL) 2(1H,3H) IMIDAZOLONE; 2 IMIDAZOLIDINONE DERIVATIVE; ANTIFUNGAL AGENT; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CANDIDIASIS; CRYPTOCOCCUS NEOFORMANS; DRUG SYNTHESIS; GROWTH INHIBITION; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; OPTICAL ROTATION; ORAL DRUG ADMINISTRATION;

EID: 0032943827     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.351     Document Type: Article

References (9)

1. Part VII: Tasaka A., Kitazaki T., Tsuchimori N., Matsushita Y., Hayashi R., Okonogi K., Itoh K., Chem. Pharm. Bull., 45, 321-326 (1997).
2. Kitazaki T., Tamura N., Tasaka A., Matsushita Y., Hayashi R., Okonogi K., Itoh K., Chem. Pharm. Bull., 44, 314-327 (1996).
3. a) Itoh K., Okonogi K., Tasaka A., Hayashi R., Tamura N., Tsuchimori N., Kitazaki T., Matsushita Y., Obita J., Abstr. of the 36th Interscience Conference on Antimicrobial Agents and Chemotherapy, New Orleans, F74, p. 112 (1996);
4. b) Okonogi K., Itoh K., Tasaka A., Kitazaki T., Hayashi R., Obita J., Kitamoto N., Tsuchimori N., Abstr. of the 17th Symposium on Medicinal Chemistry, Tsukuba, 1-P-35, p. 124 (1997).
5. Tasaka A., Tamura N., Matsushita Y., Teranishi K., Hayashi R., Okonogi K., Itoh K., Chem. Pharm. Bull., 41, 1035-1042 (1993).
6. Tasaka A., Tamura N., Matsushita Y., Kitazaki T., Hayashi R., Okonogi K., Itoh K., Chem. Pharm. Bull., 43, 432-440 (1995).
7. 2 was developed in our laboratories: Yoshida T., Jono K., Okonogi K., Antimicrob. Agents Chemother., 41, 1349-1351 (1997).
8. A similar result was obtained in our previous work: Tasaka A., Tsuchimori N., Kitazaki T., Hiroe K., Hayashi R., Okonogi K., Itoh K., Chem. Pharm. Bull., 43, 441-449 (1995).
9. Considerable decomposition was observed during attempted isolation of the triflate. Therefore, the concentrated eluate containing the triflate was used directly in the subsequent nucleophilic displacement reaction.