title: Novel ultrasound-promoted parallel synthesis of trifluoroatrolactamide library via a one-pot Passerini/hydrolysis reaction sequence and their fungicidal activities.
abstract: An ultrasound-promoted one-pot Passerini/hydrolysis reaction sequence has been developed for the synthesis of trifluoroatrolactamide derivatives using a diverse range of trifluoroacetophenones and isonitriles in acetic acid. Parallel synthesis in a centrifuge tube using a noncontact ultrasonic cell crusher was used in this study as an efficient method for the rapid generation of combinatorial trifluoroatrolactamide libraries, and subsequent biochemical evaluation of the resulting compounds indicated that they possessed excellent broad-spectrum fungicidal activities. N-(4-chlorophenyl)-2-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxypropanamide and N-(4-chlorophenyl)-3,3,3-trifluoro-2-hydroxy-2-(4-methoxyphenyl)propanamide, in particular, showed significant fungicidal activities against all of the fungal species tested in the current study.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry and ‡National Pesticide Engineering Research Center (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Shu-Jing
authors.initials: SJ
authors.lastname: Yu
authors.forename: Cong
authors.initials: C
authors.lastname: Zhu
authors.forename: Qiang
authors.initials: Q
authors.lastname: Bian
authors.forename: Can
authors.initials: C
authors.lastname: Cui
authors.forename: Xiu-Jiang
authors.initials: XJ
authors.lastname: Du
authors.forename: Zheng-Ming
authors.initials: ZM
authors.lastname: Li
authors.forename: Wei-Guang
authors.initials: WG
authors.lastname: Zhao
mesh_terms: D000813:Anilides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D020650:Combinatorial Chemistry Techniques; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000187:drug effects* / Q000254:growth & development; D006868:Hydrolysis; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D010666:Phenylpropionates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013010:Sonication; D013329:Structure-Activity Relationship
chemical_list: D000813:Anilides; D000935:Antifungal Agents; C000593128:N-(4-chlorophenyl)-2-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxypropanamide; C000593129:N-(4-chlorophenyl)-3,3,3-trifluoro-2-hydroxy-2-(4-methoxyphenyl)propanamide; D010666:Phenylpropionates