212890-35-2

Upstream product

• 1774-47-6 trimethylsulfoxonium iodide 
• 127001-03-0 (2R)-2',4'-Difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone 
• 135270-08-5 4-[(2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propionyl]morpholine 
• 110-87-2 3,4-dihydro-2H-pyran 
• 126918-16-9 (R)-1-(2,4-difluorophenyl)-2-hydroxypropan-1-one 
• 161457-73-4 (R)-1-(2,4-Difluoro-phenyl)-2-trimethylsilanyloxy-propan-1-one 
• 161457-74-5 (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(2,4-difluoro-phenyl)-propan-1-one 

Downstream Products

• 844879-56-7 (3R)-2-(2,4-difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-1-(1H-1,2,4-triazol-1-yl)2-butanol 
• 912812-70-5 (2R,3R)-2-(2,4-difluorophenyl)-3-(5-nitro-1H-indazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 912812-72-7 (2R,3R)-3-(5-amino-1H-indazol-1-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 912810-58-3 (2R,3R)-2-(2,4-difluorophenyl)-3-(3-methyl-5-nitro-1H-indazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 912811-29-1 (2R,3R)-2-(2,4-difluorophenyl)-3-(4-fluoro-3-methyl-1H-indazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 

Relevant academic research and scientific papers

Discovery of novel indazole-linked triazoles as antifungal agents

The in vitro and in vivo activities of a series of (2R, 3R)-2-(2,4-difluorophenyl)-3-(substituted indazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol as potential antifungal agents are described. In particular, the analog 12j having 5-bromo substitution on the indazole ring exhibited significant antifungal activity against a variety of fungal cultures (Candida spp. and Aspergillus spp.). In addition, oral administration of 12j showed its excellent efficacy against Candida albicans in a murine infection model and the significantly improved survival rates of the infected mice.

ANTIFUNGAL AZOLE DERIVATIVES HAVING A FLUOROVINYL MOIETY AND PROCESS FOR THE PREPARATION THEREOF

An azole derivative of formula (I) having a fluorovinyl moiety or a pharmaceutically acceptable salt thereof is superior to the conventional antifungal drugs in antifungal activity against a wide spectrum of pathogenic fungi, and has advantageously low toxicity.

Optically active azole derivatives, their production and use

A process for preparing a compound of the formula (IV) or a salt thereof, , wherein R1 is an optionally substituted aliphatic or aromatic hydrocarbon residue or an optionally substituted aromatic heterocyclic group, one of Y and Z is a nitrogen atom and t

A rational approach to chiral α-hydroxy aryl ketones from chiral aryl epoxides via regioselective, stereo retentive oxidative epoxide opening: Its application to the synthesis of antifungal Sch 42427/SM 9164

A new, mild method for the direct conversion of chiral aryl epoxides to hydroxy-protected chiral α-hydroxy aryl ketones with complete retention of the chiral center and good regioselectivity has been established. An application of this new reaction to the synthesis of antifungal Sch 42427/SM 9164 is also described.

Optically active antifungal azoles. I. Synthesis and antifungal activity of (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2- butanol and its stereoisomers

(2R,3R)-2-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2- butanol [(2R,3R)-7] and its stereoisomers [(2S,3R)-, (2S,3S)- and (2R,3S)-7] were prepared from the optically active oxiranes 6 by a newly developed ring- opening reaction and evaluated for antifungal activity. The thiol (2R,3R)-7 showed extremely potent antifungal activity in vitro and in vivo. The optically active oxirane (2R,3S)-6, a useful intermediate for the synthesis of sulfur-containing antifungal azoles 5, was synthesized from methyl (R)- lactate [(R)-8] via eight steps in a stereocontrolled manner. The key step in the synthesis is the Grignard reaction of an amide derivative [(R)-12a] of (R)-lactic acid with 2,4-difluorophenyl-magnesium bromide (13).