85654-07-5Relevant articles and documents
Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates
Hong, Kai,Morken, James P.
supporting information, p. 9252 - 9254 (2013/07/26)
We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)s
Catalytic intermolecular hetero-dehydro-diels-alder cycloadditions: Regioand diasteroselective synthesis of 5,6-dihydropyridin-2-ones
Fernandez-Garcia, Jesus Manuel,Fernandez-Rodriguez, Manuel A.,Aguilar, Enrique
supporting information; experimental part, p. 5172 - 5175 (2011/12/04)
A novel catalyzed intermolecular heterodehydro-Diels-Alder reaction between push-pull 1,3-dien-5-ynes and aldimines or silylaldimines is reported. The sequence is promoted both by gold(I) or silver(I) catalysts and leads to the diastereo- and regioselective formation of 5,6- dihydropyridin-2-ones.
Asymmetric synthesis of propargylamides via 3,3′-disubstituted binaphthol-modified alkynylboronates
Wu, T. Robert,Chong, J. Michael
, p. 15 - 18 (2007/10/03)
(Chemical Equation Presented) Alkynylboronates derived from 3,3′-disubstituted-2,2′-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective s
3,4-dihydro-1-isoquinolinamines: A novel class of nitric oxide synthase inhibitors with a range of isoform selectivity and potency
Beaton, Haydn,Hamley, Peter,Nicholls, David J,Tinker, Alan C,Wallace, Alan V
, p. 1023 - 1026 (2007/10/03)
3-Phenyl-3,4-dihydro-1-isoquinolinamine is a weak inhibitor of iNOS and nNOS. Structural variation of 5a results in inhibitors with a range of potency and selectivity for the NOS enzymes, including a potent and very selective iNOS inhibitor 5j.
A trans-stereoselective synthesis of 3-halo-4-alkyl(aryl)-NH-azetidin-2-ones
Bandini, Elisa,Favi, Gianfranco,Martelli, Giorgio,Panunzio, Mauro,Piersanti, Giovanni
, p. 1077 - 1079 (2007/10/03)
Conrotatory ring closure of 1-halo-3-aza-4-alkyl-1,3-dienes in refluxing toluene gives rise to 3-halo-4-aryl-2-azetidinones in satisfactory yields. Dehalogenation of the resulting β-lactams by tris(trimethylsilyl)silane furnished 3-unsubstituted azetidino
Lithium perchlorate mediated three component reaction for the preparation of primary amines
Saidi, Mohammad R.,Javanshir, Shahrzad,Mojtahedi, Mohammad M.
, p. 330 - 331 (2007/10/03)
In the presence of lithium perchlorate in diethyl ether, LPDE, a three- component reaction between aldehydes, sodium hexamethyldisilazane or lithium hexamethyldisilazane, LHMDS, and different nucleophiles proceeds smoothly to afford primary amines in good yields.
Convenient Access to Primary Amines by Employing the Barbier-Type Reaction of N-(Trimethylsilyl)imines Derived from Aromatic and Aliphatic Aldehydes
Gyenes, Ferenc,Bergmann, Kathryn E.,Welch, John T.
, p. 2824 - 2828 (2007/10/03)
A new versatile preparation of primary amines via benzylation of aromatic and aliphatic aldimines is described. Sonochemical and traditional methods for generation of the reactive intermediates are compared and contrasted. Competitive reactions were analyzed via free energy relationships to support the proposed alkylative mechanism.
GPIIb/IIIa integrin antagonists with the new conformational restriction unit, trisubstituted β-amino acid derivatives, and a substituted benzamidine structure
Hayashi, Yoshio,Katada, Jun,Harada, Takeo,Tachiki, Akira,Iijima, Kiyoko,Takiguchi, Yoshimi,Muramatsu, Michiko,Miyazaki, Hiroshi,Asari, Tohru,Okazaki, Takeo,Sato, Yoshimi,Yasuda, Emiko,Yano, Mako,Uno, Isao,Ojima, Iwao
, p. 2345 - 2360 (2007/10/03)
Ethyl N-[3-(2-fluor-4-(thiazolidin-3-y](imino)methyl)benzoyl)amino-2,2- dimethylpentanoyl]piperidine-4-acetate 40 (NSL-96184) is a highly potent and orally active fibrinogen receptor antagonist, which is characterized by the presence of the trisubstituted β-amino acid residue, 3-ethyl-2,2-dimethyl- β-alanine. This compound was developed on the basis of the SAR study of N- [3-N-4-amidinobenzoyl)amino-2,2-dimethyl-3-phenylpropionyl]piperidine-4- acetic acid 1 (NSL-95301) with the derivatization focused on the central trisubstituted β-amino acid unit as well as the basic amidinobenzoyl unit, and the esterification of the carboxyl group for prodrug composition. Compound 1, which was reported in our previous study, was discovered by the application of combinatorial chemistry. The molecular modeling study suggests that the trisubstituted β-amino acid unit is responsible for fixing the molecule to its active conformation. Compound 40 showed an excellent profile in the in vitro and in vivo studies for its human platelet aggregation inhibitory activity and oral availability in guinea pigs. This oral availability largely depends on the modification of the amidino group with a cyclic secondary amine, i.e., thiazolidine in 40. In in vivo studies, the onset of the antiplatelet action of 40 is very fast after oral administration, whereas its duration of action is relatively short. These results suggest that 40 has an excellent therapeutic potential, especially for antithrombotic treatment in the acute phase. 3-Substituted-2,2-dimethyl- β-amino acid residues would serve as new and useful linear templates to restrict the conformational flexibility of peptidomimetics.
N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents
Vidal, Joelle,Damestoy, Stephanie,Guy, Laure,Hannachi, Jean-Christophe,Aubry, Andre,Collet, Andre
, p. 1691 - 1709 (2007/10/03)
This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.
Pharmacological studies of 1-(p-chlorophenyl)propanol and 2-(1-hydroxy-3-butenyl)phenol: Two new non-narcotic analgesics designed by molecular connectivity
Garcia-March,Garcia-Domenech,Galvez,Anton-Fos,De Julian-Ortiz,Giner-Pons,Recio-Iglesias
, p. 10 - 15 (2007/10/03)
Molecular topology has been applied to the design of new analgesic drugs. Linear discriminant analysis and connectivity functions were used to design two potentially suitable drugs which were synthesized and tested for analgesic properties by the acetic acid-induced abdominal constriction test in mice and the tail-flick test in rats. In mice, the compound 1-(p-chlorophenyl)propanol showed higher analgesic activity, both intraperitoneally and orally, than acetylsalicylic acid. 2-(1-Hydroxy-3-butenyl)phenol exhibited a lesser protective effect (70% of that shown by acetylsalicylic acid). In rats, acetylsalicylic acid gave the greatest protection against pain when administered intraperitoneally, while 1-(p-chlorophenyl)propanol was the most active orally. The 2-(1-hydroxy-3-butenyl)phenol, both intraperitoneally and orally, showed the least protective effect. These results demonstrated the peripheral analgesic properties of the selected compounds, thus confirming the validity of the molecular design method.