- Aliphatic amino carboxylic and amino phosphonic acids, amino nitriles and amino tetrazoles as cellular rescue agents
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Novel compounds of the formula I are described: wherein: R1=(CH2)mCH3 where m is 0 or an integer in the range from 1 to 16, or an alkenyl, alkynyl, alkoxy, alkylthio, or alkyl sulfinyl group having from 2 to 17 carbon atoms, R2=H, CH3 or CH2CH3 R3=H or CH3 R4=H or CH3 R5=lower alkyl having from 1 to 5 carbon atoms n is an integer in the range from 1 to 3, and X is carboxyl (COOH) or carbalkoxy (COOR5), cyano (C≡N), phosphonic acid (PO3H2), phosphonate ester (PO3[R5]2) or 5-tetrazole, and pharmaceutically acceptable salts thereof. Preferably, the compounds are optically pure enantiomers of the R- or S-configuration in which R3=R4=R5=H, R2=CH3 and R1 is a saturated aliphatic chain of one to five carbon atoms. The compounds are useful as cellular rescue agents.
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Page/Page column 8
(2008/06/13)
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- Rearrangement of Azidomalonic Esters
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Dimethyl azidomalonate (4) is photolyzed under loss of nitrogen and rearrangement of one methoxycarbonyl group to form the mixture of Z and E isomers of the α,β-unsaturated amino acid esters 8 and 9.On photolysis of isopropyl- and isobutylazidomalonates 10 migration of the alkyl group is observed exclusively.The (alkylimino)malonates 14 so formed have been hydrogenated and hydrolyzed to give the N-alkylglycine derivatives 16.
- Frank, Juergen,Stoll, Gerhard,Musso, Hans
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p. 1990 - 1996
(2007/10/02)
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- Synthesis of Strombine. A New Method for Monocarboxymethylation of Primary Amines
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Many common methods for monocarboxymethylation of primary amines give various amounts of dialkylated by-products.In this work the reaction of two equivalents of glyoxilic acid with representative primary aliphatic and aromatic amines, as well as with amino acids and a dipeptide, is shown to give only the N-(carboxymethyl)-N-formyl derivative of the amine under mild conditions in carboxylic acid solvents.Hydrolysis then produces the monocarboxymethylated primary amine in good to exellent overall yield.Proof that the intermediate product is not obtained via the Leuckart reaction is given.
- Kihlberg, Jan,Bergman, Rolf,Wickberg, Boerje
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p. 911 - 916
(2007/10/02)
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