So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Henry, Sean; Anand, Jessica P.; Brinkel, Ashley C.; McMillan, Douglas M.; Twarozynski, Jack. J.; Loo, Christian E.; Traynor, John R.; Mosberg, Henry I. researched the compound: 2-(4-(tert-Butoxycarbonyl)piperazin-1-yl)acetic acid( cas:156478-71-6 ).Synthetic Route of C11H20N2O4.They published the article 《SAR Matrices Enable Discovery of Mixed Efficacy μ-Opioid Receptor Agonist Peptidomimetics with Simplified Structures through an Aromatic-Amine Pharmacophore》 about this compound( cas:156478-71-6 ) in ACS Chemical Neuroscience. Keywords: opioid receptors peptidomimetics pharmacophore bifunctional ligands; bifunctional ligands; peptidomimetics; structure−activity relationship; δ-opioid receptor; κ-opioid receptor; μ-Opioid receptor. We’ll tell you more about this compound (cas:156478-71-6).
We previously described the development of potent μ-opioid receptor (MOR)-agonist/δ-opioid receptor (DOR)-antagonist peptidomimetic ligands as an approach toward effective analgesics with reduced side effects. In this series, a tetrahydroquinoline (THQ) or substituted Ph is employed to link two key pharmacophore elements, a dimethyltyrosine amino acid and typically an aromatic pendant. Using new and previously reported analogs, we constructed a structure-activity relationship (SAR) matrix that probes the utility of previously reported amine pendants. This matrix reveals that the MOR-agonist/DOR-antagonist properties of these ligands do not change when a tetrahydroisoquinoline (THIQ) pendant is used, despite removal of substituents on the core Ph ring. Based on this observation, we retained the THIQ pendant and replaced the Ph core with simpler aliphatic chain structures. These simpler analogs proved to be potent MOR-agonists with high variability in their effects at the DOR and the κ-opioid receptor (KOR). These data show that the amine of the THIQ pendant may be a novel pharmacophore element that favors high MOR-efficacy, whereas the aromatic ring of the THIQ pendant may produce high MOR-potency. Combined, the two pharmacophores within the THIQ pendant may be a structurally efficient means of converting opioid peptides and peptidomimetics into potent and efficacious MOR-agonists.
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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem