1,3-Benzoxazole-4-carbonitrile as a novel antifungal scaffold of β-1,6-glucan synthesis inhibitors

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• 作者：Jun-ichi Kuroyanagi ; Kazuo Kanai ; Yuuichi Sugimoto ; Takao Horiuchi ; Issei Achiwa ; Hiroshi Takeshita ; Katsuhiro Kawakami
• 关键词：Antifungal activity ; Candida species ; Bicyclic scaffold ; Fully substituted benzene
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2010
• 出版时间：1 November 2010
• 年：2010
• 卷：18
• 期：21
• 页码：7593-7606
• 全文大小：1101 K

文摘

Synthesis and in vitro antifungal evaluations of 1,3-benzoxazole-7-carbonitrile 3, 1,3-benzoxazole-4-carbonitrile 4, benzofuran 5, benzoxazine 7, and benzimidazole 8 were reported. Among them, 1,3-benzoxazole-4-carbonitrile was found to be a superior scaffold structure with moderate growth inhibition against Candida species. 1,3-Benzoxazole-4-carbonitrile 6 showed potent activity against Candida species compared to 5-desmethyl compound 4 and triazolopyridine 2. Compound 6 was efficiently prepared from versatile intermediate 24, which possessed six different substituents on the benzene ring. Conversion of benzene 24 into various 1,3-benzoxazole derivatives such as 2-aliphatic 34, 2-amino 35, and lactone 38 was demonstrated.