142037-77-2Relevant academic research and scientific papers
Development of novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation
Ettari, Roberta,Pinto, Andrea,Previti, Santo,Tamborini, Lucia,Angelo, Ilenia C.,La Pietra, Valeria,Marinelli, Luciana,Novellino, Ettore,Schirmeister, Tanja,Zappalà, Maria,Grasso, Silvana,De Micheli, Carlo,Conti, Paola
, p. 7053 - 7060 (2015/11/11)
Novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation were developed; some of them possess Ki values in the micromolar range. We studied the structure-activity relationship of these derivatives and we performed docking studies, which allowed us to find out the key interactions established by the inhibitors with the target enzyme. Biological results indicate that the nature of the P2 and P3 substituents and their binding to the S2/S3 pockets is strictly interdependent.
Hydroboration-Suzuki cross coupling of unsaturated amino acids; the synthesis of pyrimine derivatives
Collier, Philip N,Campbell, Andrew D,Patel, Ian,Taylor, Richard J.K
, p. 6117 - 6125 (2007/10/03)
Hydroboration of protected allylglycines with 9-BBN followed by Suzuki cross coupling of the resulting organoboranes proceeded smoothly giving a range of new bis-homophenylalanine and related derivatives in good yields (9 examples, 53-64%). One of the Suzuki coupling products has been elaborated to give the N-Cbz-protected natural product pyrimine. The hydroboration-Suzuki coupling of vinylglycine derivatives was also studied but was less efficient than with the allylglycine derivatives: the best results were obtained using disiamylborane·DMS as the hydroborating agent.
Synthesis of α-amino acids using amino acid γ-anion equivalents: Synthesis of 5-oxo α-amino acids, homophenylalanine derivatives and pentenylglycines
Jackson, Richard F. W.,Fraser, Joanne L.,Wishart, Neil,Porter, Barry,Wythes, Martin J.
, p. 1903 - 1912 (2007/10/03)
Treatment of protected iodohomoalanine 7 with Rieke copper leads to the formation of an organocopper reagent 10 which reacts with electrophiles in moderate yield to give enantiomerically pure α-amino acid derivatives 11, 12 and 13. Alternatively, reaction of the fully protected iodohomoalanine derivative 15 with activated zinc gives the corresponding alkylzinc iodide 14, which reacts under palladium catalysis with a range of electrophiles (aryl iodides and acid chlorides) to give the corresponding adducts 19 and 22. While the reactions with aryl iodides provide acceptable yields in THF as solvent, the corresponding reactions with acid chlorides requires dimethoxyethane or, preferably, a combination of toluene and dimethylacetamide under ultrasonication, for good results. The alkylzinc iodide 14 can be transformed into a zinc-copper reagent 16 which reacts with allylic halides, and with reactive acid chlorides, to give the corresponding adducts 221, 24-26 in reasonable yields.
