title: Novel 4H-1,3,4-oxadiazin-5(6H)-ones with hydrophobic and long alkyl chains: design, synthesis, and bioactive diversity on inhibition of monoamine oxidase, chitin biosynthesis and tumor cell.
abstract: A new series of nitrogen-containing heterocycles 4H-1,3,4-oxadiazin-5(6H)-ones derivatives with hydrophobic and long chains were designed and synthesized by direct cyclization reaction of N'-alkylation substituted aroylhydrazines with chloroacetyl chloride. The preliminary assays showed that some of the compounds displayed moderate to good inhibitory activities toward monoamine oxidase (MAO) at the concentration of 10(-5)-10(-3)M, and antitumor activities against human lung cancer A-549 and human prostate cancer PC-3 cell lines at muM level, which might provide new scaffold for anticancer agents. Furthermore, compounds 5i and 5m exhibited significant inhibitory activity on chitin biosynthesis, which might represent a novel class of highly potential inhibitors of chitin synthesis.
authors.affiliation: Shanghai Key Laboratory of Chemical Biology, Institute of Pesticides and Pharmaceuticals, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.
authors.forename: Shao-Yong
authors.initials: SY
authors.lastname: Ke
authors.forename: Xu-Hong
authors.initials: XH
authors.lastname: Qian
authors.forename: Feng-Yi
authors.initials: FY
authors.lastname: Liu
authors.forename: Ni
authors.initials: N
authors.lastname: Wang
authors.forename: Qing
authors.initials: Q
authors.lastname: Yang
authors.forename: Zhong
authors.initials: Z
authors.lastname: Li
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002686:Chitin / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D015195:Drug Design; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008175:Lung Neoplasms / Q000473:pathology; D008297:Male; D008995:Monoamine Oxidase / Q000187:drug effects; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D011471:Prostatic Neoplasms / Q000473:pathology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D008996:Monoamine Oxidase Inhibitors; D010069:Oxadiazoles; D002686:Chitin; D008995:Monoamine Oxidase