122059-33-0Relevant academic research and scientific papers
Synthesis of 4-alkoxy and 3-nitro substituted isoxazolidines by catalyzed 1,3-dipolar cycloaddition reactions of nitrones with vinyl ethers and nitro alkenes
Meske, Michael
, p. 426 - 433 (1997)
1,3-Dipolar cycloadditions of the C-phenyl-N-alkylnitrones 1,3 and the C,N-diphenylnitrone (2) with vinyl ethers 5,6 are strongly catalyzed by chiral oxazaborolidines derived from N-arylsulfonyl substituted L-α-amino acids valine and tert-butyl leucine an
High-pressure induced domino-Horner-Wadsworth-Emmons (HWE) -Michael reactions
Has-Becker,Bodmann,Kreuder,Santoni,Rein,Reiser
, p. 1395 - 1398 (2007/10/03)
A new protocol for the alkenylation of carbonyl compounds with phosphonates (Horner-Wadsworth-Emmons reaction) is described. Aldehydes react with phosphonates already at room temperature in the presence of triethylamine without further activation by Lewis-acids if high-pressure (8 kbar) is applied to the system. Based on this protocol a domino process was developed combining the HWE reaction with a Michael reaction, thus allowing the one-pot synthesis of β-amino esters, β-thio esters or β-thio nitriles.
Synthesis and Structure-Activity Relationships of 1-Acyl-4-(2-methyl-3-pyridyl)cyanomethyl)piperazines as PAF Antagonists
Carceller, Elena,Merlos, Manuel,Giral, Marta,Almansa, Carmen,Bartroli, Javier,et al.
, p. 2984 - 2997 (2007/10/02)
A second generation of (cyanomethyl)piperazines, 1-acyl-4-((2-methyl-3-pyridyl)cyanomethyl)piperazines, with increased oral activity was prepared and evaluated in vitro in PAF-induced platelet aggregation assay (PAG) and in vivo in a PAF-induced hypotension test in normotensive rats (HYP).Oral activity was ascertained through a PAF-induced mortality test in mice (MOR).Attachment of a methyl group at position 2 of our earlier pyridine derivatives resulted in an improvement of 1 order of magnitude or greater in the ID50 of the oral test.Three different types of acylsubstituents of similar potency emerge from this work: N-(diphenylmethylamino)acetyl, 3-substituted 3-hydroxy-3-phenylpropionyl, and N-substituted 3-amino-3-phenylpropionyl groups.The most interesting compounds, 26 (UR-12460, PAG IC50 = 0.040 μM, HYP, ID50 = 0.021 mg/kg iv, MOR, ID50 = 0.30 mg/kg po) and 58 (UR-12519, PAG IC50 = 0.041 μM, HYP, ID50 = 0.015 mg/kg iv, MOR, ID50 = 0.044 mg/kg po), compare favorably with WEB-2086.Compounds 26 and 58 were also tested in active anaphylactic shock (AAS) and endotoxin-induced mortality (EIM) tests.On the basis of these data, compounds 26 and 58 have been selected for further pharmacological development.
A NOVEL OXIDATIVE RING-OPENING REACTION OF ISOXAZOLIDINES: SYNTHESES OF β-AMINO KETONES AND β-AMINO ACID ESTERS FROM SECONDARY AMINES
Murahashi, Shun-Ichi,Kodera, Yoichi,Hosomi, Tatsuhide
, p. 5949 - 5952 (2007/10/02)
A novel oxidative ring-opening reaction of isoxazolidines upon treatment with an electrophile and subsequently with a base gives β-amino ketones and β-amino acid esters highly efficiently.
