Synthesis and binding affinities of novel SRIF-mimicking beta-D-glucosides satisfying the requirement for a pi-cloud at C1.
[reaction: see text] The synthesis of four bioactive analogues of the somatostatin (SRIF-14) mimetic, beta-d-glucoside (+)-2, in which the C1 indole side chain is replaced with indole surrogates, has been achieved. These congeners, possessing the naphthyl, benzothiophene, benzyl, and benzofuran substituents, were predicted to satisfy the electrostatic requirements of the tryptophan binding pocket of SRIF. Unlike the previously described C4 picolyl and pyrazinyl congeners, these ligands bind the hSST4 receptor.
Angeles
Angie R
AR
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Neagu
Irina
I
Birzin
Elizabeth T
ET
Thornton
Edward R
ER
Smith
Amos B
AB
Hirschmann
Ralph
R
D001665:Binding Sites; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D018716:Molecular Mimicry; D015394:Molecular Structure; D013004:Somatostatin / Q000737:chemistry*; D055672:Static Electricity; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry
D005960:Glucosides; D013004:Somatostatin; D014364:Tryptophan