120902-62-7Relevant academic research and scientific papers
Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides lewis bases: Highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids
Reyes-Rangel, Gloria,Bandala, Yamir,Garcia-Flores, Fred,Juaristi, Eusebio
, p. 529 - 540 (2013/09/12)
Chiral sulfoxides/N-oxides (R)-1 and (R,R)-2 are effective chiral promoters in the enantioselective allylation of α-keto ester N-benzoylhydrazone derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g to generate the corresponding N-benzoylhydrazine derivatives 4a, 4b, 4c, 4d, 4e, 4f, 4g, with enantiomeric excesses as high as 98%. Representative hydrazine derivatives 4a, 4b were subsequently treated with SmI2, and the resulting amino esters 5a, 5b with LiOH to obtain quaternary α-substituted α-allyl α-amino acids 6a, 6b, whose absolute configuration was assigned as (S), with fundament on chemical correlation and electronic circular dichroism (ECD) data. 2013 Wiley Periodicals, Inc.
Bicyclic cyanothiazolidines as novel dipeptidyl peptidase 4 inhibitors
Betancort, Juan M.,Winn, David T.,Liu, Ruzhang,Xu, Quansheng,Liu, Junjuan,Liao, Wensheng,Chen, Shu-Hui,Carney, David,Hanway, Denise,Schmeits, James,Li, Xinqiang,Gordon, Eric,Campbell, David A.
scheme or table, p. 4437 - 4440 (2010/04/05)
The synthesis and biochemical evaluation of novel cyanothiazolidine inhibitors of dipeptidyl peptidase 4 (DPP4) is described. Their main structural feature is a constrained bicyclic core that prevents the intramolecular formation of inactive cyclic species. The inhibitors show good to moderate biochemical potency against DPP4 and display distinct selectivity profiles towards DPP7, DPP8 and DPP9 depending on their substitution.
Constrained cyano compounds
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Page/Page column 22, (2010/02/15)
Certain constrained cyano compounds are useful as inhibitors of post-proline/alanine cleaving amino-dipeptidases. Accordingly, these compounds can be employed, alone or with another therapeutic agent, to treat diabetes (especially, Type II diabetes), hyperglycemia, Syndrome X, diabetic complications, hyperinsulinemia, obesity, atherosclerosis and related diseases, as well as various immunomodulatory diseases and chronic inflammatory bowel disease.
A rapid approach to amino-acid derivatives by [2,3]-stevens rearrangement
Arboré, Amélie P.A.,Cane-Honeysett, Daniel J.,Coldham, Iain,Middleton, Mark L.
, p. 236 - 238 (2007/10/03)
Allylation of amino-acid esters gives rise to intermediate quaternary ammonium salts, which undergo proton abstraction to give ylides and [2,3]- sigmatropic rearrangement. The resulting α-amino-acid derivatives can be subjected to N-deallylation to provid
