title: Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates.
abstract: A series of ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates were prepared through the metal-catalyzed domino reaction of alkylidene malonates and 1,4-butynediol under a one-pot reaction condition at room temperature. Their in vitro anti-proliferative activities were subsequently evaluated in A549, QGY and HeLa cells. The majority of the compounds showed potent anti-tumor activity against HeLa cells. In particular, compound 3l was the most potent compound with IC(50) value of 5.4 μM. For the first time, the X-ray structure of the anti-tumor ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates is determined.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China.
authors.forename: Tiantian
authors.initials: T
authors.lastname: Wang
authors.forename: Jia
authors.initials: J
authors.lastname: Liu
authors.forename: Hanyu
authors.initials: H
authors.lastname: Zhong
authors.forename: Huan
authors.initials: H
authors.lastname: Chen
authors.forename: Zhiliang
authors.initials: Z
authors.lastname: Lv
authors.forename: Yikai
authors.initials: Y
authors.lastname: Zhang
authors.forename: Mingfeng
authors.initials: M
authors.lastname: Zhang
authors.forename: Dongping
authors.initials: D
authors.lastname: Geng
authors.forename: Chunjuan
authors.initials: C
authors.lastname: Niu
authors.forename: Yongmei
authors.initials: Y
authors.lastname: Li
authors.forename: Ke
authors.initials: K
authors.lastname: Li
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D002264:Carboxylic Acids; D005663:Furans; D011714:Pyrans