183962-51-8Relevant articles and documents
Asymmetric synthesis of α-cycloalkylalkyl substituted methanamines
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, (2008/06/13)
This invention relates to process for asymmetrically producing enantiomerically pure α-cycloalkylalkyl substitututed methanamines from α-pinene. One key step of the process of this invention utilizes the oxidation product of α-pinene, hydroxy pinanone, as a chiral auxiliary to direct the stereoselective alkylation of the corresponding ketimine. This invention also relates to key intermediates useful in the processes referred to herein.
Benzoxazolamines and Benzothiazolamines: Potent, Enantioselective Inhibitors of Leukotriene Biosynthesis with a Novel Mechanism of Action
Lazer, Edward S.,Miao, Clara K.,Wong, Hin-Chor,Sorcek, Ronald,Spero, Denice M.,et al.
, p. 913 - 923 (2007/10/02)
A series of benzoxazolamine and benzothiazolamine analogs that inhibit leukotriene (LT) biosynthesis are described.The initial lead, (S)-N-(benzothiazol-2-yl)phenylalanine ethyl ester (5a), was discovered in a screening program for inhibition of Ca-ionophore-A23187-induced LTB4 release in human polymorphonuclear leukocytes (IC50 0.23 μM).Through structural modification, it was determined that hydrophobic substituents in the 5-position and replacement of the phenyl ring of phenylalanine with a cyclohexyl group greatly enhance potency.Several ester bioisosteres that retain potency and enantiomeric selectivity are described.Lead optimization culminated in (S)-N--5-methyl-2-benzoxazolamine (43b), IC50 0.001 μM.The compounds described are not inhibitors of 5-lipoxygenase but, rather, act at the level of arachidonic acid release.
THE RESOLUTION OF RACEMIC AMINES BY THE FORMATION OF DIASTEREOMERIC AMIDES WITH AMINO ACIDS
Miao, Clara K.,Sorcek, Ronald,Nagel, Juergen H.
, p. 87 - 91 (2007/10/03)
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