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Literature DB >> 18922035

A concise synthesis of pawhuskin A.

Jeffrey D Neighbors¹, Matthew J Buller, Kelly D Boss, David F Wiemer.

Abstract

Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner-Wadsworth-Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2008 PMID： 18922035 PMCID： PMC6679901 DOI： 10.1021/np800351c

Source DB: PubMed Journal: J Nat Prod ISSN： 0163-3864 Impact factor: 4.050

11 in total

Review 1. Analgesic substances derived from natural products (natureceuticals).

Authors: Christopher R McCurdy; Stephen S Scully
Journal: Life Sci Date: 2005-10-10 Impact factor: 5.037

2. Synthesis of nonracemic 3-deoxyschweinfurthin B.

Authors: Jeffrey D Neighbors; John A Beutler; David F Wiemer
Journal: J Org Chem Date: 2005-02-04 Impact factor: 4.354

Review 3. Kappa opioids as potential treatments for stimulant dependence.

Authors: Thomas E Prisinzano; Kevin Tidgewell; Wayne W Harding
Journal: AAPS J Date: 2005-10-19 Impact factor: 4.009

Review 4. Salvinorin A analogs as probes in opioid pharmacology.

Authors: Thomas E Prisinzano; Richard B Rothman
Journal: Chem Rev Date: 2008-05 Impact factor: 60.622

5. Differential effects of protein-modifying reagents on receptor binding of opiate agonists and antagonists.

Authors: G W Pasternak; H A Wilson; S H Snyder
Journal: Mol Pharmacol Date: 1975-05 Impact factor: 4.436

6. Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest.

Authors: Brent J Yoder; Shugeng Cao; Andrew Norris; James S Miller; Fidy Ratovoson; Jeremi Razafitsalama; Rabodo Andriantsiferana; Vincent E Rasamison; David G I Kingston
Journal: J Nat Prod Date: 2007-02-28 Impact factor: 4.050

7. Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series.

Authors: Nolan R Mente; Andrew J Wiemer; Jeffrey D Neighbors; John A Beutler; Raymond J Hohl; David F Wiemer
Journal: Bioorg Med Chem Lett Date: 2006-12-12 Impact factor: 2.823

8. New geranyl stilbenes from Dalea purpurea with in vitro opioid receptor affinity.

Authors: Gil Belofsky; April N French; David R Wallace; Summer L Dodson
Journal: J Nat Prod Date: 2004-01 Impact factor: 4.050

9. BF3 x Et2O-mediated cascade cyclizations: synthesis of schweinfurthins F and G.

Authors: Nolan R Mente; Jeffrey D Neighbors; David F Wiemer
Journal: J Org Chem Date: 2008-09-17 Impact factor: 4.354

10. Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist.

Authors: Bryan L Roth; Karen Baner; Richard Westkaemper; Daniel Siebert; Kenner C Rice; SeAnna Steinberg; Paul Ernsberger; Richard B Rothman
Journal: Proc Natl Acad Sci U S A Date: 2002-08-21 Impact factor: 11.205

7 in total

1. Schweinfurthin natural products induce regression of murine melanoma and pair with anti-PD-1 therapy to facilitate durable tumor immunity.

Authors: Kathleen M Kokolus; Jeremy S Haley; Emily J Koubek; Raghavendra Gowda; Saketh S Dinavahi; Arati Sharma; David F Claxton; Klaus F Helm; Joseph J Drabick; Gavin P Robertson; Jeffrey D Neighbors; Raymond J Hohl; Todd D Schell
Journal: Oncoimmunology Date: 2018-11-11 Impact factor: 8.110

A concise synthesis of pawhuskin A.

Review 1. Analgesic substances derived from natural products (natureceuticals).

2. Synthesis of nonracemic 3-deoxyschweinfurthin B.

Review 3. Kappa opioids as potential treatments for stimulant dependence.

Review 4. Salvinorin A analogs as probes in opioid pharmacology.

5. Differential effects of protein-modifying reagents on receptor binding of opiate agonists and antagonists.

6. Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest.

7. Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series.

8. New geranyl stilbenes from Dalea purpurea with in vitro opioid receptor affinity.

9. BF3 x Et2O-mediated cascade cyclizations: synthesis of schweinfurthins F and G.

10. Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist.

1. Schweinfurthin natural products induce regression of murine melanoma and pair with anti-PD-1 therapy to facilitate durable tumor immunity.

2. Electrophilic aromatic prenylation via cascade cyclization.

3. Selective opioid growth factor receptor antagonists based on a stilbene isostere.

4. Direct conversion of benzylic and allylic alcohols to phosphonates.

5. Substitution of a triazole for the central olefin in biologically active stilbenes.

6. A selective delta opioid receptor antagonist based on a stilbene core.

7. Stilbenes as κ-selective, non-nitrogenous opioid receptor antagonists.