107202-62-0Relevant academic research and scientific papers
Synthesis of chiral iodo-N,O-acetonide aminal scaffolds via an efficient cascade reaction of amino acid-derived epoxides
Paige Souder,Evans, Zachary M.,Driver, Joshua A.,Pozzo, Eric J.,Lampkins, Andrew J.
scheme or table, p. 6908 - 6910 (2012/02/15)
Novel amino acid-derived iodo-N,O-acetonide aminals were developed as chiral, non-epimerizable scaffolds to facilitate complex molecule synthesis. These scaffolds are readily prepared from commercially available amino acid derivatives in ≤6 steps, contain an orthogonally-protected β-hydroxy amine moiety, and feature a directly reactive alkyl-iodide group for facile substitution chemistry. Further, a novel ring opening/cyclization cascade reaction was developed to prepare these compounds efficiently (59-72%) from readily available epoxide derivatives.
DIAMINOPROPANOL RENIN INHIBITORS
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Page/Page column 92, (2008/06/13)
Described are diaminopropanols of which are orally active and bind to renin to inhibit its activity. They are useful in the treatment or amelioration of diseases associated with elevated levels of renin activity or in the treatment of aspartic protease me
A convenient, stereodivergent approach to the enantioselective synthesis of N-Boc-aminoalkyl epoxides
Castejon, Patricia
, p. 3019 - 3022 (2007/10/02)
An efficient, stereodivergent and enantioselective synthesis of N-Boc-aminoalkyl epoxides has been developed. Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-diols, and after a change in the nitrogen protecting group, an intramol
Aminodiol HIV Protease Inhibitors. 1. Design, Synthesis, and Preliminary SAR
Barrish, Joel C.,Gordon, Eric,Alam, Masud,Lin, Pin-Fang,Bisacchi, Gregory S.,et al.
, p. 1758 - 1768 (2007/10/02)
A series of HIV protease inhibitors containing a novel C2 symmetrical "aminodiol" core structure were prepared from amino acid starting materials.The ability of the aminodiols to inhibit HIV replication in cell culture is comparable to their ability to inhibit the isolated enzyme, a result compatible with good cell membrane penetration by this class of compounds.Optimization of the structure-activity in this series led to aminodiol 9a (Ki = 100 nM; ED50(HIV-1) = 80 nM) containing P1/P1' benzyl and P2/P2' Boc substituents.Compound 9a is a selective inhibito r of HIV protease versus other aspartyl proteases such as human renin, human cathepsin D, and porcine pepsin.In addition, 9a is equipotent against HIV-1 and HIV-2 in cell culture and demonstrates similar activity in infected T-lymphocytes and PBMCs.After iv and oral administration in rats, 9a displayed significant oral bioavailability (ca. 40percent) and a promising plasma elimination half-life (4 h).
Renin inhibitors containing C-termini derived from mercaptoheterocycles
Ashton,Cantone,Meurer,Tolman,Greenlee,Patchett,Lynch,Schorn,Strouse,Siegl
, p. 2103 - 2112 (2007/10/02)
A series of transition-state analogues having heterocyclythio C-termini has been synthesized and evaluated for inhibition of human renin. Addition of mercaptoheterocycles to a chiral Boc-amino epoxide intermediate led, after several steps, to the target [
A Synthesis of Protected Aminoalkyl Epoxides from α-Amino Acids
Luly, Jay R.,Dellaria, Joseph F.,Plattner, Jacob J.,Soderquist, Jeffrey L.,Yi, Nwe
, p. 1487 - 1492 (2007/10/02)
The synthesis of alkylamino epoxides C is presented.Key steps include the synthesis of amino aldehyde 5 by reduction (DIBAH) of ester 3 or by oxidation of N-protected amino alcohol 4, both edducts of which are derived from amino acids.A study of the olefination of aldehyde 5 with unstabilized ylides is presented, and protected allylic amino 6, obtained in good to excellent optical purity, is oxidized (MCPBA) to epoxide C.Threo selectivity is observed in the epoxidation reaction.
