Synthesis, Biological Activities and Conformational Studies of Somatostatin Analogs

Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures

“…For a typical structure 6, the deviation of about 2.8 in q from the ideal 0 /180 value of a cyclohexane ring is mainly due to the bulk effect of the N(CH 3 …”

“…The three starting materials (4-CH 3 The synthesis of all compounds 1e6 began with the reagents being mixed at ice-bath temperature and subsequent warming to room temperature. For the preparation of 1, a solution of cycloheptylamine (7.6 mmol) in dry CHCl 3 (5 ml) was added to a solution of 4-CH 3 For the synthesis of 3, a solution of hexamethylene imine (8.0 mmol) in dry CHCl 3 (10 ml) was added to a solution of (4-CH 3 eC 6 H 4 C(O)NH)P(O)Cl 2 (2.0 mmol) in the same solvent (20 ml) at 273 K. After stirring for 4 h, the solvent was removed in vacuo and the solid obtained was washed with distilled water.…”

“…For the preparation of 1, a solution of cycloheptylamine (7.6 mmol) in dry CHCl 3 (5 ml) was added to a solution of 4-CH 3 For the synthesis of 3, a solution of hexamethylene imine (8.0 mmol) in dry CHCl 3 (10 ml) was added to a solution of (4-CH 3 eC 6 H 4 C(O)NH)P(O)Cl 2 (2.0 mmol) in the same solvent (20 ml) at 273 K. After stirring for 4 h, the solvent was removed in vacuo and the solid obtained was washed with distilled water. Compound 4 was obtained by applying a similar procedure as for 3 but by using 4-methylpiperidine (7.2 mmol) and CCl 3 C(O)NHP(O)Cl 2 (1.8 mmol).…”

Improvement of drug-like properties of peptides: the somatostatin paradigm

“…Additional chemical modifications used in order to produce restricted conformation and selective ligands include insertion of a peptoid residue [60,61]. Peptoid analogs of L-363,301, a cyclic analog which will be further discussed in Section 5.3, were screened for sst binding.…”

Utilizing the intramolecular Fukuyama–Mitsunobu reaction for a flexible synthesis of novel heterocyclic scaffolds for peptidomimetic drug design

“…As part of our efforts to design and synthesize compounds displaying an increased selectivity to the somatostatin subtype receptors and enhanced in vivo stability, [1][2][3][4][5] we were interested in a heterocyclic scaffold-based approach to somatostatin analogs.…”