Design and Synthesis of 14α-Methyl-15-aza-D-homosterols as Novel Antimycotics

Roland E. Dolle; Lawrence I. Kruse; H. S. Allaudeen

doi:10.1021/jm00164a065

Design and Synthesis of 14α-Methyl-15-aza-D-homosterols as Novel Antimycotics

Roland E. Dolle, Lawrence I. Kruse, H. S. Allaudeen

Center for Drug Discovery

Research output: Contribution to journal › Article › peer-review

35 Scopus citations

Abstract

A novel series of 14α-methyl-15-aza-D-homosterols 3-7 has been synthesized. These compounds display significant antimycotic activity in vitro (MIC = 0.8-3.1 µg/mL) that compares quite favorably to the activity observed for fluconazole (MIC = 0.8 µg/mL). Azasterols 3 and 4 were active in vivo as reflected in the increased survival time of Candida albicans infected mice. The antimycotic activity of 3-7 is hypothesized to be a consequence of the inhibition of fungal 14,15-sterol reductase.

Original language	English
Pages (from-to)	877-880
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	33
Issue number	2
DOIs	https://doi.org/10.1021/jm00164a065
State	Published - Feb 1990

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title = "Design and Synthesis of 14α-Methyl-15-aza-D-homosterols as Novel Antimycotics",

abstract = "A novel series of 14α-methyl-15-aza-D-homosterols 3-7 has been synthesized. These compounds display significant antimycotic activity in vitro (MIC = 0.8-3.1 µg/mL) that compares quite favorably to the activity observed for fluconazole (MIC = 0.8 µg/mL). Azasterols 3 and 4 were active in vivo as reflected in the increased survival time of Candida albicans infected mice. The antimycotic activity of 3-7 is hypothesized to be a consequence of the inhibition of fungal 14,15-sterol reductase.",

author = "Dolle, {Roland E.} and Kruse, {Lawrence I.} and Allaudeen, {H. S.}",

year = "1990",

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pages = "877--880",

journal = "Journal of Medicinal Chemistry",

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AU - Dolle, Roland E.

AU - Kruse, Lawrence I.

AU - Allaudeen, H. S.

PY - 1990/2

Y1 - 1990/2

N2 - A novel series of 14α-methyl-15-aza-D-homosterols 3-7 has been synthesized. These compounds display significant antimycotic activity in vitro (MIC = 0.8-3.1 µg/mL) that compares quite favorably to the activity observed for fluconazole (MIC = 0.8 µg/mL). Azasterols 3 and 4 were active in vivo as reflected in the increased survival time of Candida albicans infected mice. The antimycotic activity of 3-7 is hypothesized to be a consequence of the inhibition of fungal 14,15-sterol reductase.

AB - A novel series of 14α-methyl-15-aza-D-homosterols 3-7 has been synthesized. These compounds display significant antimycotic activity in vitro (MIC = 0.8-3.1 µg/mL) that compares quite favorably to the activity observed for fluconazole (MIC = 0.8 µg/mL). Azasterols 3 and 4 were active in vivo as reflected in the increased survival time of Candida albicans infected mice. The antimycotic activity of 3-7 is hypothesized to be a consequence of the inhibition of fungal 14,15-sterol reductase.

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ER -

Design and Synthesis of 14α-Methyl-15-aza-D-homosterols as Novel Antimycotics

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