250137-79-2Relevant academic research and scientific papers
PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OF DISEASES RELATED TO NEUROTROPHINES
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Page 30, (2008/06/13)
The present invention refers to pharmaceutical preparations including as active compounds 3-aza-bicyclo[3.2.1]octane derivatives of general formula (I) and/or their dimers of general formula (II) and (III) acting as agonists of human neurotrophines. Therefore, such compounds of formula (I), (II) and (III) are useful for treatment of diseases in which the neurotrophine functions are involved in defect, particularly of Nerve Growth Factor (NGF), such as neurodegenerative diseases of central nervous system (CNS), acquired immundeficiency due to a reduced NGF biodisponibility, or morbous conditions in which the stimulus of neoangiogenesis process is convenient.
Oligomers of enantiopure bicyclic γ/δ-amino acids (BTAa). 1. Synthesis and conformational analysis of 3-Aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic acid oligomers (PolyBTG)
Machetti, Fabrizio,Ferrali, Alessandro,Menchi, Gloria,Occhiato, Ernesto G.,Guarna, Antonio
, p. 3987 - 3990 (2007/10/03)
(Matrix Presented) A series of dimeric through pentameric oligomers of a bicyclic γ/δ-amino acid (BTG) were synthesized using peptide coupling methods in solution with PyBroP or HATU. The analysis of 1H NMR and CD spectra suggests that these ol
Synthesis and reactivity of bicycles derived from tartaric acid and α- amino acids: A novel class of conformationally constrained dipeptide isosteres based upon enantiopure 3-aza-6,8-dioxabicyclo[3.2.1] octane-7- carboxylic acid
Guarna, Antonio,Guidi, Antonio,Machetti, Fabrizio,Menchi, Gloria,Occhiato, Ernesto G.,Scarpi, Dina,Sisi, Sauro,Trabocchi, Andrea
, p. 7347 - 7364 (2007/10/03)
3-Aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic acids (named BTAa) derived from (R,R)-, (S,S)-, or meso-tartaric acid and natural (L), unnatural (D), or unusual α-amino acids are described as conformationally constrained dipeptide isosteres. The general strategy developed for their preparation has required the transformation of the amino acids into the corresponding N- benzylamino alcohols, followed by the PyBroP-promoted condensation with the monomethyl ester of the suitable 2,3-di-O-isopropylidenetartaric acid. Oxidation of the hydroxy group to aldehyde and subsequent acid-catalyzed trans-acetalization with the two hydroxy groups of the tartaric acid moiety provided 3-aza-2-oxo-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic acid methyl esters [named BTAa(O)] in good yield and, in most cases, as single enantiopure diastereoisomers. This strategy has been applied to the preparation of BTAa(O) starting from (R,R)-, (S,S)-, or meso-tartaric acid and glycine, L- and D-phenylalanine, L- and D-alanine, and (±)- phenylglycine. In the cases of glycine, L- and D-phenylalanine, and L- and D- alanine, the selective reduction by BH3·DMS of the amide group succeeding to the cyclization step, or the reduction of both amide and ester functions followed by reoxidation of the hydroxy to carboxylic group, provided in good yield the 3-aza-3-benzyl-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic acids (or their methyl ester)BTAa, having the side chain of the amino acid precursors at position 4. The stability and rigidity of the bicyclic skeleton, the complete control of all the stereocenters, the possibility of introducing the side chains of L- or D-amino acids, and the demonstrated compatibility with the conditions required for solid-phase peptide synthesis make the BTAa compounds potential dipeptide isosteres useful for the synthesis of modified peptides.
