804566-95-8

Basic information

• Product Name: 11-bromoundecanyl-2-cyanoethyl fluconazole phosphate
• Synonyms: 11-bromoundecanyl-2-cyanoethyl fluconazole phosphate
• CAS NO: 804566-95-8
• Molecular Weight: 672.51
• Mol File: 804566-95-8.mol

Chemical Properties

• CAS DataBase Reference: 11-bromoundecanyl-2-cyanoethyl fluconazole phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 11-bromoundecanyl-2-cyanoethyl fluconazole phosphate(804566-95-8)
• EPA Substance Registry System: 11-bromoundecanyl-2-cyanoethyl fluconazole phosphate(804566-95-8)

Safety Data

• Hazardous Substances Data: 804566-95-8(Hazardous Substances Data)

Upstream product

• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 86386-73-4 fluconazole 
• 804567-08-6 diisopropyl-phosphoramidous acid 11-bromo-undecyl ester 2-cyano-ethyl ester 

Relevant articles and documents

AZOLE DERIVATIVES AND METHODS FOR MAKING THE SAME

The present invention is broadly directed to azole derivatives that exhibit antifungal activity and methods for making the same. In one aspect, the invention includes carboxylic acid and phosphate ester derivatives of fluconazole that exhibit antifunga

Carboxylic acid and phosphate ester derivatives of fluconazole: Synthesis and antifungal activities

Carboxylic acid and phosphate ester derivatives of fluconazole were synthesized and evaluated in vitro against Cryptococcus neoformans, Candida albicans, and Aspergillus niger. Two classes of fluconazole derivatives, (a) carboxylic acid esters and (b) fatty alcohol and carbohydrate phosphate esters, were synthesized and evaluated in vitro against Cryptococcus neoformans, Candida albicans, and Aspergillus niger. All carboxylic acid ester derivatives of fluconazole (1a-l), such as O-2-bromooctanoylfluconazole (1g, MIC = 111 μg/mL) and O-11-bromoundecanoylfluconazole (1j, MIC = 198 μg/mL), exhibited higher antifungal activity than fluconazole (MIC ≥ 4444 μg/mL) against C. albicans ATCC 14053 in SDB medium. Several fatty alcohol phosphate triester derivatives of fluconazole, such as 2a, 2b, 2f, 2g, and 2h, exhibited enhanced antifungal activities against C. albicans and/or A. niger compared to fluconazole in SDB medium. For example, 2-cyanoethyl-ω-undecylenyl fluconazole phosphate (2b) with MIC value of 122 μg/mL had at least 36 times greater antifungal activity than fluconazole against C. albicans in SDB medium. Methyl-undecanyl fluconazole phosphate (2f) with a MIC value of 190 μg/mL was at least 3-fold more potent than fluconazole against A. niger ATCC 16404. All compounds had higher estimated lipophilicity and dermal permeability than those for fluconazole. These results demonstrate the potential of these antifungal agents for further development as sustained-release topical antifungal chemotherapeutic agents.