55685-95-5Relevant academic research and scientific papers
Synthesis of Variously Functionalized Azabicycloalkane Scaffolds by Domino Metathesis Reactions
Serra, Massimo,Peviani, Elena Giulia,Bernardi, Eric,Colombo, Lino
, p. 11091 - 11101 (2017/10/27)
7,5-Fused azabicycloalkane scaffolds, carrying a quaternary stereocenter at C3 position of the lactam ring, can act as effective reverse-turn mimics and have proven to be useful intermediates for the preparation of Arg-Gly-Asp (RGD)-based cyclopentapeptides (cRGD) with nanomolar activity as αvβ3/αvβ5 integrin antagonists. Here, we report the synthesis of new azabicycloalkane scaffolds endowed at the C6 position with a para-substituted phenethyl side chain, which could be exploited to obtain cRGD-based bioconjugates that may find promising applications in anticancer therapy. By performing a domino cross enyne metathesis/ring-closing metathesis (CEYM/RCM) in the presence of styrene derivatives, followed by catalytic hydrogenation of the diene system, we easily converted a dipeptide precursor into the desired C6-functionalized azabicycloalkane scaffolds. The presence of a suitably protected p-amino group on the styrene moiety could be exploited, after deprotection, either to directly conjugate a bioactive compound or to introduce a suitable spacer between the cRGD unit and the bioactive compound.
BEMP-promoted C(4)-alkylation of 4-alkyloxazol-5(4 H)-ones: A rapid and efficient route to α,α-dialkyl-α-amino acids
Lee, Yeon-Ju,Seo, Jeyoung,Kim, Dong-Guk,Park, Hyeung-Geun,Jeong, Byeong-Seon
, p. 701 - 704 (2013/05/09)
Rapid and efficient C(4)-alkylation of 4-alkyloxazol-5(4H)-ones has been achieved by the utilization of BEMP as base. 4,4-Dialkyloxazol-5(4H)-ones, which can easily be hydrolyzed into free α,α-dialkyl-α-amino acids, were obtained in high yields (up to 99%
Enantioselective quaternization of 4-substituted oxazol-5-(4H)-ones using recoverable Cinchona-derived dimeric ammonium salts as phase-transfer organocatalysts
Tari, Silvia,Avila, Angel,Chinchilla, Rafael,Najera, Carmen
experimental part, p. 176 - 180 (2012/05/20)
Dimeric anthracenyldimethyl-derived Cinchona ammonium salts are used as chiral organocatalysts (5 mol %) for the enantioselective 4-alkylation of 4-substituted azlactones. The corresponding adducts bearing a new quaternary center were obtained with up to
Enantiomerically enriched alpha , alpha -distributed amino acids and method
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, (2008/06/13)
Compositions and methods for the preparation of enantiomerically enriched alpha , alpha -disubstituted amino acid precursors are presented. Briefly, allylic electrophiles are alkylated with oxazolones in the presence of a base and catalytic quantities of
