title: Synthesis and bioactivities of novel piperazine-containing 1,5-Diphenyl-2-penten-1-one analogues from natural product lead.
abstract: A series of novel 1,5-Diphenyl-2-penten-1-one analogues (7a-h, 8a-h) with piperazine moiety have been designed and synthesized on the basis of natural product 1,5-Diphenyl-2-penten-1-one (I). All the synthesized compounds were evaluated in vitro for anti-plant pathogenic fungi activities and insecticidal activities. The results indicated that most of these analogues exhibited moderate antifungal activities and moderate to good insecticidal activities. Amongst them, the most potent 7c, 7e and 7h keep a mortality of 100% against larva of mosquito at the concentration of 1mg/L. Initial structure-activity relationship (SAR) analysis showed that, a methyl group can influence the biological activities of these compounds significantly, the compounds with N'-unsubstituted piperazine showed much better antifungal activities and larvicidal activity against mosquito than the compounds with N'-methylated piperazine. In addition, the larvicidal activity against mosquito had sharply decline when the substituent on benzene ring was changed from 4-position to 2 or 3-position.
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Gaofei
authors.initials: G
authors.lastname: Xu
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Xinling
authors.initials: X
authors.lastname: Yang
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Biaobiao
authors.initials: B
authors.lastname: Jiang
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Peng
authors.initials: P
authors.lastname: Lei
authors.affiliation: Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, 100193, China.
authors.forename: Xili
authors.initials: X
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
authors.forename: Qingmin
authors.initials: Q
authors.lastname: Wang
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Xuebo
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Yun
authors.initials: Y
authors.lastname: Ling
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000737:chemistry / Q000494:pharmacology; D009033:Culicidae / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D006801:Humans; D007313:Insecta / Q000187:drug effects; D007306:Insecticides / Q000737:chemistry* / Q000494:pharmacology*; D010422:Pentanones / Q000737:chemistry* / Q000494:pharmacology*; D010879:Piperazines / Q000737:chemistry* / Q000494:pharmacology*; D010935:Plant Diseases / Q000382:microbiology / Q000517:prevention & control; D010944:Plants / Q000382:microbiology
chemical_list: C433345:1,5-diphenyl-2-penten-1-one; D000935:Antifungal Agents; D001688:Biological Products; D007306:Insecticides; D010422:Pentanones; D010879:Piperazines
keywords: 1,5-Diphenyl-2-penten-1-one; Bioactivities; Piperazine; Stellera chamaejasme L.; Synthesis