title: Synthesis and anti-proliferative activity of novel azazerumbone conjugates with chalcones.
abstract: The conjugation of azazerumbone ((3E,7E,11E)-5,5,8,12-tetramethylazacyclododeca-3,7,11-trien-2-one (7)) and 2,4-dihydroxychalcones was carried out for the preparation of novel target compounds 9a-g with 1-ethylene-4-methylene-1,2,3-triazole linker and 10a-f with propylene linker between amide nitrogen of azazerumbone and 4-hydroxy group of chalcone. The anti-proliferative activity of these compounds against the LU-1, Hep-G2, MCF-7 and SW480 human cancer cell lines were significantly improved compared to those of azazerumbone or zerumbone. The anti-proliferative activities of (3E,7E,11E)-1-((1-(2-(3-hydroxy-4-((E)-3-(3-methoxyphenyl)acryloyl)phenoxy)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-5,5,8,12-tetramethyl azacyclododeca-3,7,11-trien-2-one (9b) and (3E,7E,11E)-1-(3-(4-((E)-3-(3,4,5-trimethoxyphenyl)acryloyl)phenoxy)propyl)-5,5,8,12-tetramethylazacyclododeca-3,7,11-trien-2-one (10d) are nearly comparable to those of ellipticine.
authors.affiliation: Vietnam-Russia Tropical Centre, 2-Nguyen Van Huyen, Cau Giay, Hanoi, Viet Nam.
authors.forename: Vuong Van
authors.initials: VV
authors.lastname: Truong
authors.affiliation: Vietnam-Russia Tropical Centre, 2-Nguyen Van Huyen, Cau Giay, Hanoi, Viet Nam.
authors.forename: Tran Duy
authors.initials: TD
authors.lastname: Nam
authors.affiliation: Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam.
authors.forename: Truong Ngoc
authors.initials: TN
authors.lastname: Hung
authors.affiliation: Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam.
authors.forename: Nguyen Thi
authors.initials: NT
authors.lastname: Nga
authors.affiliation: Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam.
authors.forename: Pham Minh
authors.initials: PM
authors.lastname: Quan
authors.affiliation: Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam. Electronic address: chinhluuvan@gmail.com.
authors.forename: Luu Van
authors.initials: LV
authors.lastname: Chinh
authors.affiliation: College of Pharmacy and Institute of Drug Research and development, Chungnam National University, Daejeon 34134, Republic of Korea. Electronic address: jungshh@cnu.ac.kr.
authors.forename: Sang-Hun
authors.initials: SH
authors.lastname: Jung
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D047188:Chalcones / Q000138:chemical synthesis* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004611:Ellipticines / Q000494:pharmacology; D006801:Humans; D007769:Lactams / Q000138:chemical synthesis / Q000494:pharmacology*; D012717:Sesquiterpenes / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D047188:Chalcones; D004611:Ellipticines; D007769:Lactams; D012717:Sesquiterpenes; C000609110:azazerumbone; C034192:ellipticine; C403304:zerumbone
keywords: Anti-proliferative activity; Azazerumbone; Chalcone; Conjugate; Zerumbone