Synthesis and antifungal activities of myristic acid analogs

Keykavous Parang; Edward E. Knaus; Leonard I. Wiebe; Soroush Sardari; Mohsen Daneshtalab; Ferenc Csizmadia

Synthesis and antifungal activities of myristic acid analogs

Keykavous Parang, Edward E. Knaus, Leonard I. Wiebe, Soroush Sardari, Mohsen Daneshtalab, Ferenc Csizmadia

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

Abstract

Myristic acid analogs that are putative inhibitors of N-myristoyl transferase were tested in vitro for activity against yeasts (Saccharomyces cerevisiae, Candida albicans, Cryptococcus neoformans) and filamentous fungi (Aspergillus niger). Several (±)-2-halotetradecanoic acids including (±)-2-bromotetradecanoic acid (14c) exhibited potent activity against C. albicans (MIC = 39 μM), C. neoformans (MIC = 20 μM), S. cerevisiae (MIC = 10 μM), and A. niger (MIC <42 μM) in RPMI 1640 media. Improved synthetic methods have been developed for the synthesis of 12-fluorododecanoic acid (12a) and 12-chlorododecanoic acid (12c). Three novel fatty acids, 12-chloro-4-oxadodecanoic acid (8a), 12-phenoxydodecanoic acid (12i), and 11-(4-iodophenoxy)-undecanoic acid (13d) were also synthesized and tested.

Original language	English (US)
Pages (from-to)	475-482
Number of pages	8
Journal	Archiv der Pharmazie
Volume	329
Issue number	11
State	Published - Nov 1996
Externally published	Yes

Keywords

antifungal activity
myristic acid
myristoyl CoA:protein N-myristoyltransferase (NMT)
structure-activity relationships

ASJC Scopus subject areas

Drug Discovery
Organic Chemistry
General Chemistry
Pharmacology

Cite this

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title = "Synthesis and antifungal activities of myristic acid analogs",

abstract = "Myristic acid analogs that are putative inhibitors of N-myristoyl transferase were tested in vitro for activity against yeasts (Saccharomyces cerevisiae, Candida albicans, Cryptococcus neoformans) and filamentous fungi (Aspergillus niger). Several (±)-2-halotetradecanoic acids including (±)-2-bromotetradecanoic acid (14c) exhibited potent activity against C. albicans (MIC = 39 μM), C. neoformans (MIC = 20 μM), S. cerevisiae (MIC = 10 μM), and A. niger (MIC <42 μM) in RPMI 1640 media. Improved synthetic methods have been developed for the synthesis of 12-fluorododecanoic acid (12a) and 12-chlorododecanoic acid (12c). Three novel fatty acids, 12-chloro-4-oxadodecanoic acid (8a), 12-phenoxydodecanoic acid (12i), and 11-(4-iodophenoxy)-undecanoic acid (13d) were also synthesized and tested.",

keywords = "antifungal activity, myristic acid, myristoyl CoA:protein N-myristoyltransferase (NMT), structure-activity relationships",

author = "Keykavous Parang and Knaus, {Edward E.} and Wiebe, {Leonard I.} and Soroush Sardari and Mohsen Daneshtalab and Ferenc Csizmadia",

year = "1996",

month = nov,

language = "English (US)",

volume = "329",

pages = "475--482",

journal = "Archiv der Pharmazie",

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T1 - Synthesis and antifungal activities of myristic acid analogs

AU - Parang, Keykavous

AU - Knaus, Edward E.

AU - Wiebe, Leonard I.

AU - Sardari, Soroush

AU - Daneshtalab, Mohsen

AU - Csizmadia, Ferenc

PY - 1996/11

Y1 - 1996/11

N2 - Myristic acid analogs that are putative inhibitors of N-myristoyl transferase were tested in vitro for activity against yeasts (Saccharomyces cerevisiae, Candida albicans, Cryptococcus neoformans) and filamentous fungi (Aspergillus niger). Several (±)-2-halotetradecanoic acids including (±)-2-bromotetradecanoic acid (14c) exhibited potent activity against C. albicans (MIC = 39 μM), C. neoformans (MIC = 20 μM), S. cerevisiae (MIC = 10 μM), and A. niger (MIC <42 μM) in RPMI 1640 media. Improved synthetic methods have been developed for the synthesis of 12-fluorododecanoic acid (12a) and 12-chlorododecanoic acid (12c). Three novel fatty acids, 12-chloro-4-oxadodecanoic acid (8a), 12-phenoxydodecanoic acid (12i), and 11-(4-iodophenoxy)-undecanoic acid (13d) were also synthesized and tested.

AB - Myristic acid analogs that are putative inhibitors of N-myristoyl transferase were tested in vitro for activity against yeasts (Saccharomyces cerevisiae, Candida albicans, Cryptococcus neoformans) and filamentous fungi (Aspergillus niger). Several (±)-2-halotetradecanoic acids including (±)-2-bromotetradecanoic acid (14c) exhibited potent activity against C. albicans (MIC = 39 μM), C. neoformans (MIC = 20 μM), S. cerevisiae (MIC = 10 μM), and A. niger (MIC <42 μM) in RPMI 1640 media. Improved synthetic methods have been developed for the synthesis of 12-fluorododecanoic acid (12a) and 12-chlorododecanoic acid (12c). Three novel fatty acids, 12-chloro-4-oxadodecanoic acid (8a), 12-phenoxydodecanoic acid (12i), and 11-(4-iodophenoxy)-undecanoic acid (13d) were also synthesized and tested.

KW - antifungal activity

KW - myristic acid

KW - myristoyl CoA:protein N-myristoyltransferase (NMT)

KW - structure-activity relationships

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M3 - Article

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AN - SCOPUS:0029728832

SN - 0365-6233

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JF - Archiv der Pharmazie

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ER -

Synthesis and antifungal activities of myristic acid analogs

Abstract

Keywords

ASJC Scopus subject areas

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