Spiro[2.2]pentane as a dissymmetric scaffold for conformationally constrained analogues of glutamic acid: focus on racemic 1-aminospiro[2.2]pentyl-1,4-dicarboxylic acids.
In search for novel conformationally constrained analogues of L-glutamic acid, a diastereodivergent synthesis of the four 1-aminospiro[2.2]pentyl-1,4-dicarboxylic acid racemic pairs is reported along with their stereochemical assignment, conformational analysis, and preliminary biological evaluation as potential glutamate (ionotropic and metabotropic) ligands.
Pellicciari
Roberto
R
Dipartimento di Chimica e Tecnologia del Farmaco, Università di Perugia, Via del Liceo, 1, 06123 Perugia Italy. rp@unipg.it
Marinozzi
Maura
M
Camaioni
Emidio
E
del Carmen Nùnez
Maria
M
Costantino
Gabriele
G
Gasparini
Fabrizio
F
Giorgi
Gianluca
G
Macchiarulo
Antonio
A
Subramanian
Natarajan
N
D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018698:Glutamic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010420:Pentanes / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D003998:Dicarboxylic Acids; D010420:Pentanes; D013141:Spiro Compounds; D018698:Glutamic Acid