Total Synthesis of AMF-26, an Antitumor Agent for Inhibition of the Golgi System, Targeting ADP-Ribosylation Factor 1
作者： Isamu Shiina , Yuma Umezaki , Yoshimi Ohashi , Yuta Yamazaki , Shingo Dan
DOI: 10.1021/JM301695C
关键词: Chemistry 、 Golgi apparatus 、 Intramolecular force 、 Stereochemistry 、 Total synthesis 、 Bioassay 、 Conjugated system 、 Biochemistry 、 Stereoselectivity 、 Aldol reaction 、 Cell culture
摘要: An effective method for the total synthesis of 1 (AMF-26), a potentially promising new anticancer drug that disrupts Golgi system by inhibiting ADP-ribosylation factor (Arf1) activation, has been developed first time. The construction chiral linear precursor (a key to synthesis) was achieved asymmetric aldol reaction followed computer-assisted predictive stereoselective intramolecular Diels–Alder reaction. global antitumor activity totally synthetic against variety human cancer cells assessed using panel 39 cell lines (JFCR39), and it shown strongly inhibited growth several at concentrations less than 0.04 μM. Biological assays novel derivatives, 26 31, which have different side-chains C-4 positions in Δ1,2-octalin backbone, disclosed importance suitable structure side-chain containing conjugated multidouble bonds.
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