152885-90-0Relevant academic research and scientific papers
Catalytic asymmetric allylation of aldehydes using the chiral (salen)chromium(III) complexes
Kwiatkowski, Piotr,Cha?adaj, Wojciech,Jurczak, Janusz
, p. 5116 - 5125 (2007/10/03)
The enantioselective addition of allylstannanes to glyoxylates and glyoxals, as well as simple aromatic and aliphatic aldehydes, catalyzed by chiral (salen)Cr(III) complexes, has been studied. The reaction proceeded smoothly for the reactive 2-oxoaldehydes and allyltributyltin in the presence of small amounts (1-2 mol %) of (salen)Cr(III)BF4 (1b) under mild, undemanding conditions. However, in the case of other simple aldehydes, the use of high-pressure conditions is required to obtain good yields. Classic chromium catalyst 1b, easily prepared from the commercially available chloride complex 1a, affords homoallylic alcohols usually in good yield and with enantiomeric purity of 50-79% ee. The stereochemical results are rationalized on the basis of the proposed model.
Non-peptide Renin Inhibitors Containing 2-(((3-Phenylpropyl)phosphoryl)oxy)alkanoic Acid Moieties as P2-P3 Replacements
Raddatz, Peter,Minck, Klaus-Otto,Rippmann, Friedrich,Schmitges, Claus-Jochen
, p. 486 - 497 (2007/10/02)
A series of novel renin inhibitors containing 2-(((3-phenylpropyl)phosphoryl)oxy)alkanoic acid moieties as P2-P3 surrogates are presented.The P2-P3 mimetics were obtained from (ω-phenylalkyl)phosphinic acids 1a-c and 2-hydroxyalkanoic acid benzyl esters 2a-f by N,N'-dicyclohexylcarbodiimide-mediated coupling and subsequent oxidation with sodium metaperjodate.Ester cleavage of these derivatives and coupling with P1-P'1 transition-state mimetics I-VII provided highly selective compounds with inhibitory potencies in the lower nanomolar range.Small renin inhibitors, such as analogues 8c and 8h with molecular weights of 539 and 537, respectively, could be prepared.These compounds exhibited IC50 values of about 20 nM against human plasma renin.Compound 7i was examined in vivo for its hypotensive effect.In salt-depleted cynomolgus monkeys, 7i inhibited plasma renin activity almost completely and lowered blood pressure after oral adiministration of a dose of 30 mg/kg.
