Synthesis and bioactivity studies of 1‐adamantanamine derivatives of peptides

Abstract

Small enkephalin-related peptides containing a 1-adamantanamine moiety coupled through an amide linkage at the C-terminus were synthesized. Several of the compounds showed high mu opioid activity and mu receptor selectivity. The new adamantanamine derivatives were also examined for antiviral activity against HIV-1 in a cell culture system. Some of them inhibited syncytia formation even when the antigen assay gave evidence for viral replication.

The Lipophilic Bullet Hits the Targets: Medicinal Chemistry of Adamantane Derivatives

“…619 C -terminally adamantane modified tri- and dipeptide fragments derived from enkephalins ( vide supra ) like 304 and 305 on the other hand were identified as functional opioid receptor agonists. 620 In electrically stimulated longitudinal muscle stripes of guinea pig ileum, an assay for μ-opioid receptors, 304 has an IC 50 = 413 ± 10 nM while 305 was more active at IC 50 = 4 ± 0.3 nM. In mouse vas defens muscle strips, a model to study δ opioid receptors, 304 was markedly less active (IC 50 = 1510 ± 340 nM), while 305 also showed nanomolar activity (K i = 42 ± 3 nM).…”

1-Adamantanamine-based triazole-appended organosilanes as chromogenic “naked-eye” and fluorogenic “turn-on” sensors for the highly selective detection of Sn2+ ions

“…29 Moreover, 1-adamantanamine has been used as an important chemical entity owing to its multitude of rich biological properties in the pharmacological chemistry field, making it a highly appealing material. 30,31 However, the optical sensing properties of 1-adamantanamine have been sparsely explored to the best of our knowledge. Encouraged by the propitious potential, we developed chemosensors 4a-d via the synchronization of 1-adamantanamine, a Schiff-base motif, a 1,2,3-triazole ring, and an organosilane moiety in a single framework to create a versatile research approach for the selective detection of Sn 2+ ions.…”

Rotation Barriers of 1‐Adamantyl‐Csp3 Bonds Measured with Dynamic NMR

“…Adamantane is a highly rigid group with a hydrophobicity similar to that of n ‐hexane, that can contribute to ligand binding with a greatly lower conformational entropy loss than an unbranched alkyl group. Thus, adamantane has been used as a fragment in drug molecules targeting different proteins, and the study of its flexibility is worth investigating. In previous studies, we have investigated the effect of the presence of adamantane ring in the conformational properties and bond rotational free energy barriers as a spiro junction, or as 1‐adamantyl and 2‐adamantyl group substituent at the one end of a Csp 3 ‐Csp 3 bond, using Dynamic NMR (DNMR) .…”