Non-peptide δ opioid agonists and antagonists (Part II)

Dondio, Giulio; Ronzoni, Silvano; Petrillo, Paola

doi:10.1517/13543776.9.4.353

Cited by 42 publications

(26 citation statements)

References 46 publications

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“…However, it was shown to be a δ-agonist only 3-fold less potent than SL-3111 and possibly more selective. It is difficult to compare these results with those for BW-and SNC80-related compounds because similar changes in the piperazine ring have not been made, though a recent report on patent applications 20 not yet granted indicates that another class of compounds, the diarylalkenylamines, may be related. Unfortunately nothing has appeared in the peer-reviewed literature, and further discussion is thus not possible at this time.…”

Section: Resultsmentioning

confidence: 99%

Exploring the Structure−Activity Relationships of [1-(4-tert-Butyl-3‘-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), A High-Affinity and Selective δ-Opioid Receptor Nonpeptide Agonist Ligand

et al. 1999

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SL-3111 [1-(4-tert-butyl-3'-hydroxy)benzhydryl-4-benzylpiperazine] is a de novo designed, high-affinity and selective nonpeptide peptidomimetic agonist of the delta-opioid receptor. In a previous report we had described the unique biological characteristics of this ligand and also a need for further structural evaluation.(6) To pursue this, we have introduced a completely different heterocyclic template (2 and 3), which, based on molecular modeling studies, may present the required structural features to properly orient the pharmacophore groups. We also have made more subtle changes to the original piperazine scaffold (5 and 11). The biological activities of these compounds revealed an important participation of the scaffold in the ligand-receptor interaction. To further explore functional diversity on the scaffold, we have maintained the original piperazine ring and introduced four different functionalities at position 2 of the heterocyclic ring (15a-d; a = CH(2)-O-CH(2)-Ph; b = Me; c = CH(2)Ph; d = CH(2)OH). The biological activities observed for these compounds showed a very interesting trend in terms of the steric effects of the groups introduced at this position. A decrease of almost 2000-fold in affinity and potency at the delta-receptor was observed for 15c compared with 15b. This difference may be explained if we postulate that the bioactive conformation of these peptidomimetics is close to the minimal energy conformations calculated in our study. On the basis of these findings we have realized the importance of this position to further explore and simplify the structure of future generations of peptidomimetic ligands.

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Section: Resultsmentioning

confidence: 99%

Exploring the Structure−Activity Relationships of [1-(4-tert-Butyl-3‘-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), A High-Affinity and Selective δ-Opioid Receptor Nonpeptide Agonist Ligand

et al. 1999

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“…3,138 The interest in a pure subtype selective opioid receptor antagonist is increased by reports that these types of compounds may have use in the treatment of obesity, psychosis, depression, and irritable bowel syndrome. [139][140][141][142] Receptor selectivity can be determined for opioid receptor ligands using displacement of opioid receptor subtype selective radioligands from receptor sites in membrane preparations prepared from animal brain tissue. More recently, cloned µ, δ, and κ receptors have been used to determine selectivity.…”

Section: 3) Analogues Nonselective For the Monoamine Transportermentioning

confidence: 99%

2002 Medicinal Chemistry Division Award Address: Monoamine Transporters and Opioid Receptors. Targets for Addiction Therapy

Carroll

2003

J. Med. Chem.

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“…Additionally, δ receptor agonists have been reported to stimulate respiration, act as anti‐diarrheals, and elicit immunomodulatory, anti‐depressant‐like, and gastroprotective effects 2. 3…”

Section: Introductionmentioning

confidence: 99%

A Divergent Enantioselective Synthesis of 9‐J₁‐Phytoprostane and 9‐A₁‐Phytoprostane Methyl Ester

et al. 2014

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The first syntheses of 9‐J1‐phytoprostane and 9‐A1‐phytoprostane methyl ester were achieved enantioselectively using a divergent approach from a common intermediate sulfone 4. The divergence was accomplished using a sigmatropic rearrangement (swap protocol) to give sulfone 5 in 47 % overall yield. The two upper side‐chains, with a stereodefined E double bond, were installed using consolidated Julia–Lythgoe olefination reactions of sulfones 4 and 5, with the same enantiopure α‐protected aldehyde 6.

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Non-peptide δ opioid agonists and antagonists (Part II)

Cited by 42 publications

References 46 publications

Exploring the Structure−Activity Relationships of [1-(4-tert-Butyl-3‘-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), A High-Affinity and Selective δ-Opioid Receptor Nonpeptide Agonist Ligand

Exploring the Structure−Activity Relationships of [1-(4-tert-Butyl-3‘-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), A High-Affinity and Selective δ-Opioid Receptor Nonpeptide Agonist Ligand

2002 Medicinal Chemistry Division Award Address: Monoamine Transporters and Opioid Receptors. Targets for Addiction Therapy

A Divergent Enantioselective Synthesis of 9‐J₁‐Phytoprostane and 9‐A₁‐Phytoprostane Methyl Ester

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Non-peptide δ opioid agonists and antagonists (Part II)

Cited by 42 publications

References 46 publications

Exploring the Structure−Activity Relationships of [1-(4-tert-Butyl-3‘-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), A High-Affinity and Selective δ-Opioid Receptor Nonpeptide Agonist Ligand

Exploring the Structure−Activity Relationships of [1-(4-tert-Butyl-3‘-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), A High-Affinity and Selective δ-Opioid Receptor Nonpeptide Agonist Ligand

2002 Medicinal Chemistry Division Award Address: Monoamine Transporters and Opioid Receptors. Targets for Addiction Therapy

A Divergent Enantioselective Synthesis of 9‐J1‐Phytoprostane and 9‐A1‐Phytoprostane Methyl Ester

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A Divergent Enantioselective Synthesis of 9‐J₁‐Phytoprostane and 9‐A₁‐Phytoprostane Methyl Ester