112897-08-2Relevant academic research and scientific papers
Identification and Total Synthesis of an Unstable Anticancer Macrolide Presaccharothriolide Z Produced by Saccharothrix sp. A1506
Ikeda, Hiroaki,Kakeya, Hideaki,Kuranaga, Takefumi,Nakagawa, Yusuke,Tamura, Miho,Terada, Sakahiro
supporting information, p. 7106 - 7111 (2021/09/14)
Saccharothriolides A-F are 10-membered microbial macrolides proposed to be generated from their precursors presaccharothriolides X-Z. Previously, we isolated presaccharothriolide X, and its unique natural prodrug-like properties have intrigued us. However
Synthesis and biological evaluation of truncated α-tubulin-binding pironetin analogues lacking alkyl pendants in the side chain or the dihydropyrone ring
Pa?os, Julián,Díaz-Oltra, Santiago,Sánchez-Peris, María,García-Pla, Jorge,Murga, Juan,Falomir, Eva,Carda, Miguel,Redondo-Horcajo, Mariano,Díaz, J. Fernando,Barasoain, Isabel,Marco, J. Alberto
, p. 5809 - 5826 (2013/09/12)
The preparation of several new truncated analogues of the natural dihydropyrone pironetin is described. They differ from the natural product mainly in the suppression of some of the alkyl pendants in either the side chain or the dihydropyrone ring. Their cytotoxic activity and their interactions with tubulin have been investigated. It has been found that all analogues are cytotoxic towards two either sensitive or resistant tumoral cell lines with similar IC50 values in each case, thus strongly suggesting that, like natural pironetin, they also display a covalent mechanism of action. Their cytotoxicity is, however, lower than that of the parent compound. This indicates that all alkyl pendants are necessary for the full biological activity, with the ethyl group at C-4 seemingly being particularly relevant. Most likely, the alkyl groups cause a restriction in the conformational mobility of the molecule and reduce the number of available conformations. This makes it more probable that the molecule preferentially adopts a shape which fits better into the binding point in α-tubulin.
Iridium-catalyzed allylation of chiral β-stereogenic alcohols: Bypassing discrete formation of epimerizable aldehydes
Schmitt, Daniel C.,Dechert-Schmitt, Anne-Marie R.,Krische, Michael J.
supporting information, p. 6302 - 6305 (2013/02/25)
The cyclometalated π-allyliridium 3,4-dinitro-C,O-benzoate complex modified by (R)- or (S)-Cl,MeO-BIPHEP promotes the transfer hydrogenative coupling of allyl acetate to β-stereogenic alcohols with good to excellent levels of catalyst-directed diastereose
Stereoselective total synthesis of arenastatin A, a spongean cytotoxic depsipeptide
Kotoku, Naoyuki,Narumi, Fuminori,Kato, Tomoya,Yamaguchi, Miho,Kobayashi, Motomasa
, p. 7147 - 7150 (2008/03/11)
A highly stereoselective total synthesis of arenastatin A, an extremely potent cytotoxic cyclic depsipeptide from marine sponge, was developed. The desired 7,8-β-epoxide in arenastatin A was constructed by asymmetric sulfur ylide-mediated epoxidation in g
Two Routes to Chiral Dithianes, Useful Synthons for the Preparation of Functionalised Spiroketals
Kermadec, Dominique de,Prudhomme, Michelle
, p. 7335 - 7336 (2007/10/02)
Two routes are described leading to chiral precursors for the synthesis of new substituted spiroketals.The stabilities of the methoxymethyl, tert-butyldimethylsilyl and tert-butyldiphenylsilyl hydroxyl protecting groups were tested in these reaction seque
