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Literature DB >> 28910112

Modular Approach to pseudo-Neoclerodanes as Designer κ-Opioid Ligands.

Alexander M Sherwood¹, Samuel E Williamson¹, Rachel S Crowley¹, Logan M Abbott¹, Victor W Day¹, Thomas E Prisinzano¹.

Abstract

Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of functionality about the target molecule to provide access to molecular features on salvinorin A otherwise unattainable by semisynthesis. Using this approach, a potent pseudo-neoclerodane κ-opioid receptor ligand (2) has been realized.

Entities: Chemical Gene Species

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Year: 2017 PMID： 28910112 PMCID： PMC5632227 DOI： 10.1021/acs.orglett.7b02684

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

36 in total

1. Enantioselective allyltitanation. Efficient synthesis of the C1-C14 polyol subunit of amphotericin B.

Authors: S BouzBouz; J Cossy
Journal: Org Lett Date: 2000-12-14 Impact factor: 6.005

2. The 2-methoxy methyl analogue of salvinorin A attenuates cocaine-induced drug seeking and sucrose reinforcements in rats.

Authors: Aashish S Morani; Amy Ewald; Katherine M Prevatt-Smith; Thomas E Prisinzano; Bronwyn M Kivell
Journal: Eur J Pharmacol Date: 2013-11-04 Impact factor: 4.432

3. Structure-based design, synthesis, and biochemical and pharmacological characterization of novel salvinorin A analogues as active state probes of the kappa-opioid receptor.

Authors: Feng Yan; Ruslan V Bikbulatov; Viorel Mocanu; Nedyalka Dicheva; Carol E Parker; William C Wetsel; Philip D Mosier; Richard B Westkaemper; John A Allen; Jordan K Zjawiony; Bryan L Roth
Journal: Biochemistry Date: 2009-07-28 Impact factor: 3.162

4. Chemotype-selective modes of action of κ-opioid receptor agonists.

Authors: Eyal Vardy; Philip D Mosier; Kevin J Frankowski; Huixian Wu; Vsevolod Katritch; Richard B Westkaemper; Jeffrey Aubé; Raymond C Stevens; Bryan L Roth
Journal: J Biol Chem Date: 2013-10-11 Impact factor: 5.157

5. Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist.

Authors: Thomas A Munro; Mark A Rizzacasa; Bryan L Roth; Beth A Toth; Feng Yan
Journal: J Med Chem Date: 2005-01-27 Impact factor: 7.446

6. Identification of the molecular mechanisms by which the diterpenoid salvinorin A binds to kappa-opioid receptors.

Authors: Feng Yan; Philip D Mosier; Richard B Westkaemper; Jeremy Stewart; Jordan K Zjawiony; Timothy A Vortherms; Douglas J Sheffler; Bryan L Roth
Journal: Biochemistry Date: 2005-06-21 Impact factor: 3.162

7. Synthesis and in vitro pharmacological studies of C(4) modified salvinorin A analogues.

Authors: David Y W Lee; Minsheng He; Leelakrishna Kondaveti; Lee-Yuan Liu-Chen; Zhongze Ma; Yulin Wang; Yong Chen; Jian-Guo Li; Cecile Beguin; William A Carlezon; Bruce Cohen
Journal: Bioorg Med Chem Lett Date: 2005-10-01 Impact factor: 2.823

8. Addressing Structural Flexibility at the A-Ring on Salvinorin A: Discovery of a Potent Kappa-Opioid Agonist with Enhanced Metabolic Stability.

Authors: Alexander M Sherwood; Rachel Saylor Crowley; Kelly F Paton; Andrew Biggerstaff; Benjamin Neuenswander; Victor W Day; Bronwyn M Kivell; Thomas E Prisinzano
Journal: J Med Chem Date: 2017-04-19 Impact factor: 7.446

Review 5. Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide.

Authors: Soumen Chakraborty; Susruta Majumdar
Journal: Biochemistry Date: 2020-09-22 Impact factor: 3.162

5 in total

Modular Approach to pseudo-Neoclerodanes as Designer κ-Opioid Ligands.

1. Enantioselective allyltitanation. Efficient synthesis of the C1-C14 polyol subunit of amphotericin B.

2. The 2-methoxy methyl analogue of salvinorin A attenuates cocaine-induced drug seeking and sucrose reinforcements in rats.

3. Structure-based design, synthesis, and biochemical and pharmacological characterization of novel salvinorin A analogues as active state probes of the kappa-opioid receptor.

4. Chemotype-selective modes of action of κ-opioid receptor agonists.

5. Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist.

6. Identification of the molecular mechanisms by which the diterpenoid salvinorin A binds to kappa-opioid receptors.

7. Synthesis and in vitro pharmacological studies of C(4) modified salvinorin A analogues.

8. Addressing Structural Flexibility at the A-Ring on Salvinorin A: Discovery of a Potent Kappa-Opioid Agonist with Enhanced Metabolic Stability.

9. Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers.

10. Stereochemical study of a transannular Michael reaction cascade.

Review 1. A review of salvinorin analogs and their kappa-opioid receptor activity.

Review 2. Chemical syntheses of the salvinorin chemotype of KOR agonist.

3. Dynamic Strategic Bond Analysis Yields a Ten-Step Synthesis of 20-nor-Salvinorin A, a Potent κ-OR Agonist.

4. Formal Total Synthesis of Salvinorin A.

Review 5. Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide.