Synthesis and antifungal activity of a novel series of 13-(4-isopropylbenzyl)berberine derivatives = 새로운 13-(4-아이소프로필벤질)버버린 유도체의 합성과 항진균 활성

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Title
Synthesis and antifungal activity of a novel series of 13-(4-isopropylbenzyl)berberine derivatives = 새로운 13-(4-아이소프로필벤질)버버린 유도체의 합성과 항진균 활성
Author(s)
K D Park; S J Cho; Jae Sun Moon; Sung Uk Kim
Bibliographic Citation
Bioorganic & Medicinal Chemistry Letters, vol. 20, no. 22, pp. 6551-6554
Publication Year
2010
Abstract
By replacing the methyl group of 13-(4-isopropylbenzyl)berberine 2 with various acyl, alkyl, and benzyl groups via the demethylated intermediate, 13-(4-isopropylbenzyl)berberrubine 4, a novel series of 9-O-alkyl-13-(4- isopropylbenzyl)berberine derivatives was synthesized and examined for antifungal activities against various human pathogenic fungi. The introduction of various alkyl groups led to enhanced antifungal activity but that of acyl groups resulted in decrease of the activity. Among them, 9-O-butyl-13-(4- isopropylbenzyl)berberine 6d exhibited the most potent antifungal activities against Cryptococcus neoformans, Candida species (MIC = 0.25-1 μg/ml), and Aspergillus species (MIC = 2-4 μg/ml). The compound was found to be relatively safe up to 900 mg/kg in oral administration to mice.
Keyword
13-(4-Isopropylbenzyl)berberineAntifungal activityBerberine derivativesHuman pathogenic fungi
ISSN
0960-894X
Publisher
Elsevier
DOI
http://dx.doi.org/10.1016/j.bmcl.2010.09.045
Type
Article
Appears in Collections:
Division of Biomaterials Research > Plant Systems Engineering Research > 1. Journal Articles
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