title: Synthesis and antifungal activity of novel indole-replaced streptochlorin analogues.
abstract: Based on examples of the successful applications in drug discovery of bioisosterism, a series of streptochlorin analogues in which indole has been replaced by other heterocycles has been designed and synthesized, as a continuation of our studies aimed at the discovery of novel streptochlorin analogues with improved antifungal activity. Biological testing showed that most of the indole-replaced streptochlorin analogues were inactive, though compound 6f had a broad spectrum of antifungal activity with significant activity against Alternaria solani. The SAR study demonstrated that indole ring is an essential moiety for the antifungal activity of streptochlorin analogues, promoting the idea of indole ring as a framework that might be exploited in the future.
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, PR China; Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China. Electronic address: mzzhang@njau.edu.cn.
authors.forename: Ming-Zhi
authors.initials: MZ
authors.lastname: Zhang
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, PR China; Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China.
authors.forename: Chen-Yang
authors.initials: CY
authors.lastname: Jia
authors.affiliation: Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom.
authors.forename: Yu-Cheng
authors.initials: YC
authors.lastname: Gu
authors.affiliation: Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom.
authors.forename: Nick
authors.initials: N
authors.lastname: Mulholland
authors.affiliation: Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom.
authors.forename: Sarah
authors.initials: S
authors.lastname: Turner
authors.affiliation: Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom.
authors.forename: David
authors.initials: D
authors.lastname: Beattie
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, PR China. Electronic address: njzhangwh@126.com.
authors.forename: Wei-Hua
authors.initials: WH
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China.
authors.forename: Guang-Fu
authors.initials: GF
authors.lastname: Yang
authors.affiliation: Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom.
authors.forename: John
authors.initials: J
authors.lastname: Clough
mesh_terms: D000528:Alternaria / Q000187:drug effects; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D010080:Oxazoles / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D007211:Indoles; D010080:Oxazoles; C526070:streptochlorin; C030374:indole
keywords: Active heterocycles; Antifungal activity; SAR; Streptochlorin analogues; Synthesis