120681-10-9Relevant articles and documents
Non-thiol farnesyltransferase inhibitors: utilization of an aryl binding site by 5-arylacryloylaminobenzophenones.
Mitsch, Andreas,Boehm, Markus,Wissner, Pia,Sattler, Isabel,Schlitzer, Martin
, p. 2657 - 2662 (2002)
We recently described a novel aryl binding site of farnesyltransferase. The 2-naphthylacryloyl residue was developed as an appropriate substituent for our benzophenone-based AAX-peptidomimetic capable of occupying this binding site, resulting in a non-thiol farnesyltransferase inhibitor with nanomolar activity. The activity of this inhibitor is readily explained on the basis of docking studies which show the 2-naphthyl residue fitting into the aryl binding site.
Enantioselective Synthesis of 3,4-Dihydropyran-2-ones via Phase-Transfer-Catalyzed Addition-Cyclization of Acetylacetone to Cinnamic Thioesters
Destro, Dario,Bottinelli, Carlo,Ferrari, Ludovica,Albanese, Domenico C. M.,Bencivenni, Grazia,Gillick-Healy, Malachi W.,Kelly, Brian G.,Adamo, Mauro F. A.
supporting information, p. 5183 - 5192 (2020/04/10)
Herein, we present the first example of synthesis of 3,4-dihydropyran-2-ones from cinnamic thioesters via a stereoselective phase-transfer-catalyzed domino Michael-cyclization reaction with acetylacetone. The reaction proceeded under the catalysis of Cinchona-derived quaternary ammonium phenoxide that, in combination with inorganic bases, provided 3,4-dihydropyran-2-ones in yields of up to 93% and enantioselectivities of up to 88% enantiomeric excess.
Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer
Wang, Ming-Zhong,Ku, Chuen-Fai,Si, Tong-Xu,Tsang, Siu-Wai,Lv, Xiao-Meng,Li, Xiao-Wan,Li, Zheng-Ming,Zhang, Hong-Jie,Chan, Albert S. C.
, p. 98 - 105 (2018/02/07)
Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel-Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.