541506-73-4Relevant articles and documents
Synthesis and biological evaluation of new amino acids structurally related to the antitumor agent acivicin
Conti, Paola,Roda, Gabriella,Stabile, Helena,Vanoni, Maria Antonietta,Curti, Bruno,De Amici, Marco
, p. 683 - 690 (2003)
A set of racemic conformationally constrained analogues of the antitumor antibiotic acivicin (+)-1 has been prepared through a strategy based on 1,3-dipolar cycloaddition of bromonitrile oxide to suitable dipolarophiles. The bromo analogue (2) of acivicin was also synthesized and tested as a reference compound, together with its stereoisomer 3. The antitumor properties of novel amino acids 4-7 were evaluated in vitro against human tumor cell lines. Their efficacy to inhibit glutamate synthase (GltS) from Azospirillum brasilense was also assayed. None of the studied compounds, but 2, showed significant activity.
Design of novel conformationally restricted analogues of glutamic acid
Conti, Paola,De Amici, Marco,Roda, Gabriella,Vistoli, Giulio,Stensb?l, Tine Bryan,Br?uner-Osborne, Hans,Madsen, Ulf,Toma, Lucio,De Micheli, Carlo
, p. 1443 - 1452 (2003)
Stereomeric 3-carboxy-Δ2-isoxazoline-cyclopentane amino acids, which represent restricted conformations of glutamic acid, have been prepared through a strategy based on the 1,3-dipolar cycloaddition of ethoxycarbonylformonitrile oxide to a suitably protected 1-amino-cyclopent-2-enecarboxylic acid. These amino acids, assayed at iGluRs and mGluRs, proved to be inactive. The biological data have been accounted for through the comparison of their conformational profile with that of a 3-carboxy-Δ2-isoxazolinyl proline (CIP-A) and (±)-1-aminocyclopentane-1,3-dicarboxylic acid.
