4515-23-5Relevant articles and documents
Synthesis and anticonvulsant evaluation of (R)-and (S)-3-carbobenzyloxy- amino-1-oxysuccinimides
Lee, Do-Hun
, p. 5948 - 5950 (2013/07/26)
A series of (R)-and (S)-3-carbobenzyloxy-amino-1-oxysuccinimides (5a-d) [(S)-3-carbobenzyloxy-amino-1-benzoyloxysuccinimde, (R)-3-carbobenzyloxy-amino- 1-acetyloxysuccinimde, (R)-3-carbobenzyloxy-amino-1,4-nitrobenzoyloxysuccinimde, (R)-3-carbobenzyloxyamino-1,4-fluorobenzoyloxysuccinimde] were synthesized and investigated their anticonvulsant activities in maximal electric shock seizure test and pentylenetetrazole induced seizure test.
One-pot syntheses of dissymmetric diamides based on the chemistry of cyclic monothioanhydrides. Scope and limitations and application to the synthesis of glycodipeptides
Crich, David,Sasaki, Kaname,Rahaman, Md Yeajur,Bowers, Albert A.
body text, p. 3886 - 3893 (2009/10/20)
(Chemical Equation Presented) Opening cyclic monothioanhydrides by amines provides a convenient entry into amido thioacids that can be trapped in situ by 2,4-dinitrobenzenesulfonamides, by electron-deficient azides, or by amines in the presence of Sanger's reagent leading, in each case, to dissymmetric diamides in what can be considered a one-pot, three-component coupling sequence. The use of monothiomaleic anhydride and bifunctional nucleophiles such as amino thiols provides access to heterocyclic amides. The low reactivity of cyclic monothioanhydrides toward alcohols enables the use of methanol as solvent and obviates the need for the protection of alcohols in the various reaction components. Reaction of N-benzyloxycarbonyl-L-aspartic monothioanhydride with unprotected glycosyl amines, followed by capture of the thioacid intermediate with N-sulfonyl amino acid derivatives results in a three-component convergent synthesis of glycosylated peptides.
Cyclic thioanhydrides: Linchpins for multicomponent coupling reactions based on the reaction of thioacids with electron-deficient sulfonamides and azides
Crich, David,Bowers, Albert A.
, p. 5323 - 5325 (2008/09/17)
(Chemical Equation Presented) Reaction of cyclic thioanhydrides with amines affords amides functionalized with thioacids, which can be trapped in situ with electrondeficient azides or, preferably, 2,4-dinitrobenzenesulfonamides. In this manner the cyclic thioanhydride serves as a linchpin in a three-component coupling sequence. The use of thiomaleic anhydride and a afunctional nucleophile extends the process to heterocycle synthesis, while a cyclic thioanhydride prepared from aspartic acid directly provides N-functionalized asparagine derivatives.