749177-28-4Relevant articles and documents
Synthesis and cytotoxicity of novel simplified eleutherobin analogues as potential antitumour agents
Sosonyuk, Sergey E.,Peshich, Anita,Tutushkina, Anastasia V.,Khlevin, Dmitry A.,Lozinskaya, Natalia A.,Gracheva, Yulia A.,Glazunova, Valeria A.,Osolodkin, Dmitry I.,Semenova, Marina N.,Semenov, Victor V.,Palyulin, Vladimir A.,Proskurnina, Marina V.,Shtil, Alexander A.,Zefirov, Nikolay S.
supporting information, p. 2792 - 2797 (2019/03/12)
Mixed simplified structures containing the paclitaxel and eleutherobin pharmacophore moieties were analyzed using molecular docking techniques and synthesized based on adamantane and 8-oxabicyclo[3.2.1]octane scaffolds. The crucial role of substituents' stereochemistry in biological activity is discussed. At micromolar concentrations the selected analogues interfered with tubulin dynamics in vitro and in a living organism. Furthermore, new compounds were cytotoxic against human tumour cell lines. The simplified eleutherobin analogues may be considered as prototypes of a new class of antitumour agents.
Synthesis of the tricyclic core of eleutherobin and sarcodictyins and total synthesis of sarcodictyin A
Nicolau,Xu,Kim,Ohshima,Hosokawa,Pfefferkorn
, p. 11353 - 11354 (2007/10/03)
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189. Sarcodictyin A and Sarcodictyin B, Novel Diterpenoidic Alcohols Esterified by (E)-N(1)-Methylurocanic Acid. Isolation from the Mediterranean Stolonifer Sarcodictyon roseum
D'Ambrosio, Michele,Guerriero, Antonio,Pietra, Francesco
, p. 2019 - 2027 (2007/10/02)
The Mediterranean stolonifer Sarcodictyon roseum (=Rolandia rosea) ( Cnidaria, Anthozoa, Alcyonaria, Stolonifera, Clavulariidae) is shown to contain two novel diterpenoidic alcohols esterified by (E)-N(1)-methylurocanic acid (= (E)-3-(1-methyl-1H-imidazol-4-yl)acrylic acid).They are sarcodictyin A (= (-)-(4R,4aR,7R,10S,11S,12aR,1Z,5E,8Z)-7,10-epoxy-3,4,4a,7,10,11,12,12a-octahydro-7-hydroxy-6-(methoxycarbonyl)-1,10-dimethyl-4-(1-methylethyl)benzocyclodecen-11-yl (E)-3-(1-methyl-1H-imidazol-4-yl)acrylate; (-)-1) and sarcodictyin B (the 6-(ethoxycarbonyl analogue; (-)-2).The assignment of the structures is based on 1D- and 2D-NMR data, as well as on mainly chemical transformations of (-)-1, such as transesterification with MeONa/MeOH giving methyl (E)-N(1)-methylurocanate (3) and the free alcohol (+)-4 and reduction with LiAlH4 followed by benzoylation giving dibenzoate 7.Absolute configurations are based on Horeau's method of esterification of (+)-4.