69555-16-4Relevant academic research and scientific papers
Isoform-selective thiazolo[5,4-b]pyridine S1P1 agonists possessing acyclic amino carboxylate head-groups
Reed, Anthony B.,Lanman, Brian A.,Neira, Susana,Harrington, Paul E.,Sham, Kelvin K.C.,Frohn, Mike,Pickrell, Alexander J.,Tasker, Andrew S.,Gore, Anu,Fiorino, Mike,Itano, Andrea,McElvain, Michele,Middleton, Scot,Morrison, Henry,Xu, Han,Xu, Yang,Wong, Min,Cee, Victor J.
supporting information; experimental part, p. 1779 - 1783 (2012/04/04)
Replacement of the azetidine carboxylate of an S1P1 agonist development candidate, AMG 369, with a range of acyclic head-groups led to the identification of a novel, S1P3-sparing S1P1 agonist, (-)-2-amino -4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl) phenyl)-2-methylbutanoic acid (8c), which possessed good in vivo efficacy and pharmacokinetic properties. A 0.3 mg/kg oral dose of 8c produced a statistically significant reduction in blood lymphocyte counts 24 h post-dosing in female Lewis rats.
A convenient method for the enantiomeric separation of α-amino acid esters as benzophenone imine schiff base derivatives
Huang, Hu,Xu, Wen Jun,Jin, Jing-Yu,Hong, Joon Hee,Shin, Hyun-Jae,Lee, Wonjae
experimental part, p. 1015 - 1019 (2012/10/08)
A convenient liquid chromatographic method for the separation of α-amino acid esters as benzophenone Schiff base derivatives on coated chiral stationary phases (CSPs) (Chiralcel OD-H, Chiralcel OD, Chiralpak AD-H, Chiralpak AD, and Chiralpak AS) or covalently immobilized CSPs (Chiralpak IA, Chiralpak IB, and Chiralpak IC) derived from polysaccharide derivatives is described. Benzophenone imine derivatives of α-amino acid esters were readily prepared by stirring benzophenone imine and the hydrochloride salts of α-amino acid esters in 2-propanol. The chromatographic separations were conducted at a flow rate 1.0 mL/min and a detection wavelength of 254 nm; 0.5% 2-propanol/hexane (v/v) was used on CSPs. In general, the resolution of Chiralpak IC was superior to those of the other CSPs. In addition, the resolutions of other arylimine derivatives of α-amino acid esters and the effects of different mobile phases on the enantiomeric separation of α-amino acid esters as benzophenone imine derivatives on Chiralpak IC were investigated.
Palladium catalysed asymmetric alkylation of benzophenone Schiff base glycine esters in ionic liquids
Kim, Dae Hyun,Im, Jin Kyu,Kim, Dae Won,Cheong, Minserk,Kim, Hoon Sik,Mukherjee, Deb Kumar
experimental part, p. 467 - 476 (2012/03/26)
Asymmetric alkyl substitution of various benzophenone Schiff base substrates under biphasic conditions proceeded using optically active Palladium(II) complexes. The corresponding products were obtained in high yields but with moderate enantiomeric excess (ee) . Addition of specific ionic liquids to the reaction medium enhanced reactivity and selectivity for phase transfer catalytic (PTC) glycine alkylation. It has been found that there is an anionic influence of the ionic liquids that modify the steric environment around the enolate ion. A computer-assisted molecular design of enantioselective phase-transfer catalysis with the palladium complex and the ionic liquid has been done. Indian Academy of Sciences.
Ionic liquid as an efficient promoting medium for two-phase nucleophilic displacement reactions
Louren?o, Nuno M.T.,Afonso, Carlos A.M.
, p. 789 - 794 (2007/10/03)
The use of the room temperature ionic liquid (RTIL) 1-n-butyl-3-methylimidazolium hexafluorophosphate as an efficient catalyst and solvent for several representative nucleophilic substitution reactions under aqueous-RTIL phase transfer conditions was explored. Recycling and reuse of the reaction medium was demonstrated for the azide formation.
Easy and efficient generation of reactive anions with free and supported ylides as neutral Bronsted bases
Palacios, Francisco,Aparicio, Domitila,De Los Santos, Jesús M.,Baceiredo, Antoine,Bertrand, Guy
, p. 663 - 669 (2007/10/03)
The tris(dimethylamino)-C-dimethylphosphorus ylide 5 and the tris(dimethylamino)phosphorus ylide C-bound to Merrifield's resin 6 are used as strong non-nucleophilic bases in N-alkylation reactions of β-amino phosphine oxides and α-amino acid derivatives,
Reaction of dihalocarbenes with N-Alkylidene amino acid esters and nitriles. Synthesis of aziridine and pyrrole amino acid derivatives
Khlebnikov,Novikov,Nikiforova,Kostikov
, p. 91 - 99 (2007/10/03)
Conditions for preparation of functionalized geminal dihaloaziridines by reaction of dihalocarbenes with N-benzhydrylidene amino acid esters and nitriles were found. The direction of transformations of the intermediate azomethine ylides depends on the structure of the latter, as deduced from MNDO calculations.
First Michael addition reaction of α-substituted N-diphenylmethyleneglycinate with ethyl propiolate. Synthesis of α-substituted (E)-3,4-dehydroglutamic acids
Rubio, Almudena,Ezquerra, Jesus
, p. 5823 - 5826 (2007/10/02)
(E)-α-substituted 3,4-dehydro glutamic acids 4, were prepared from ethyl N-diphenylmethyleneglycinate 5 by alkylation with a suitable alkyl halide followed by a Michael type addition reaction with ethyl propiolate, giving rise to a mixture of E/Z adducts 7/8. Sequential hydrolysis of the substituted glycine synthons 7/8 afforded the titled compounds 4 as single diastereomers.
