1,3-Benzoxazole-4-carbonitrile as a novel antifungal scaffold of β-1,6-glucan synthesis inhibitors
2010; Elsevier BV; Volume: 18; Issue: 21 Linguagem: Inglês
10.1016/j.bmc.2010.08.044
ISSN1464-3391
AutoresJun‐ichi Kuroyanagi, Kazuo Kanai, Yuuichi Sugimoto, Takao Horiuchi, Issei Achiwa, Hiroshi Takeshita, Katsuhiro Kawakami,
Tópico(s)Synthesis and biological activity
ResumoSynthesis 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.
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