117997-58-7Relevant academic research and scientific papers
Grignard addition to aldonitrones. Stereochemical aspects and application to the synthesis of C2-symmetric diamino alcohols and diamino diols
Dondoni, Alessandro,Perrone, Daniela,Rinaldi, Marilisa
, p. 9252 - 9264 (2007/10/03)
A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4- diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from β- amino-α-hydroxy aldehydes followed by reduction of the resulting N- benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3- diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV- 1 protease inhibitors.
New approaches to the asymmetric synthesis of dipeptide isosteres via β-Lactam Synthon Method
Ojima, Iwao,Wang, Hong,Wang, Tao,Ng, Edward W.
, p. 923 - 926 (2007/10/03)
New and efficient synthetic routes to dipeptide isosteres with high enantiomeric purity, e.g., hydroxyethylene, dihydroxyethylene and hydroxyethylamine isosteres, have been developed via oxiranes 6 and formyloxazolines 13 derived from N-t-Boc-β-lactams 4.
Enantioselective synthesis of N-Boc-2,2-dimethyloxazolidine-5-carbaldehydes, versatile precursors of dipeptide isosteres
Pasto, Mireia,Moyano, Albert,Pericas, Miquel A.,Riera, Antoni
, p. 1233 - 1236 (2007/10/03)
Highly enantioenriched cis and trans N-Boc-2,2-dimethyl-oxazolidine-5-carbaldehydes have been efficiently prepared from N-Boc-3-amino-1,2-alkanediols, readily available in enantiopure or enantioenriched form by Sharpless epoxidation methodology. These compounds have been converted into N-Boc-(S)-γ-[(S)-1-aminoalkyl]-γ-lactones which are key intermediates of hydroxyethylene dipeptide isosteres.
STEREOSELECTIVE SYNTHESIS OF A C-TERMINAL COMPONENT OF RENIN INHIBITORS VIA ITERATIVE HOMOLOGATION
Wagner, Adalbert,Mollath, Martina
, p. 619 - 622 (2007/10/02)
A stereoselective synthesis of an aminodiol derivative (dipeptide mimic) has been developed via iterative homologation of protonated cyclohexylalaninal (Dondoni reaction).
Synthesis of the hydroxyethylene dipeptide isostere, (2S,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanoic acid n-butyl amide
Poss,Reid
, p. 1411 - 1414 (2007/10/02)
A stereoselective synthesis of the hydroxyethylene dipeptide isostere, (2S,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanoic acid-n-butyl amide from Boc-L-phenylalanine is described.
Renin inhibitors containing new P1-P1' dipeptide mimetics with heterocycles in P1'
Raddatz,Jonczyk,Minck,Rippmann,Schittenhelm,Schmitges
, p. 3525 - 3536 (2007/10/02)
A series of renin inhibitors containing new P1-P1' dipeptide mimetics are presented. The P1-P1' mimetics were obtained from (4S,5S)-3-(tert- butoxycarbonyl)-4-(cyclohexylmethyl)-5-[(ω-mesyloxy)alkyl]-2,2- dimeth
AMINO ACID DERIVATIVES
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, (2008/06/13)
The compounds of the formula STR1 wherein A, R 1, R. sup.2, R. sup.3, R 4, R 5 and R 6 are as set forth above, are described. The compounds of formula I have an inhibitory activity on the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations for the control or prevention of high blood pressure and cardiac insufficiency.
Potent, Low Molecular Weight Renin Inhibitors Containing a C-Terminal Heterocycle: Hydrogen Bonding at the Active Site
Rosenberg, Saul H.,Dellaria, Joseph F.,Kempf, Dale J.,Hutchins, Charles W.,Woods, Keith W.,et al.
, p. 1582 - 1590 (2007/10/02)
A series of low-nanomolar renin inhibitors containing novel C-terminal heterocycles has been designed by formally cyclizing the C-terminus of a glycol-based inhibitor to the second hydroxyl.Molecular modeling suggests that the heterocyclic oxygen hydrogen
