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.
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.
Ke
Shao-Yong
SY
Shanghai Key Laboratory of Chemical Biology, Institute of Pesticides and Pharmaceuticals, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.
Qian
Xu-Hong
XH
Liu
Feng-Yi
FY
Wang
Ni
N
Yang
Qing
Q
Li
Zhong
Z
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
D000970:Antineoplastic Agents; D008996:Monoamine Oxidase Inhibitors; D010069:Oxadiazoles; D002686:Chitin; D008995:Monoamine Oxidase