Synthesis and binding affinities of novel SRIF-mimicking β-D-glucosides satisfying the requirement for a π-cloud at C1

被引：13

作者：

Angeles, AR

Neagu, I

Birzin, ET

Thornton, ER

Smith, AB

Hirschmann, R ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

[2] Merck Res Labs, Dept Biochem & Physiol, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 06期

关键词：

D O I：

10.1021/ol050119i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：1121 / 1124

页数：4

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