Flexible Total Synthesis of 11‐Deoxylandomycins and Their Non‐Natural Analogues by Way of Asymmetric Metal Catalysis

2019 ◽  
Vol 132 (6) ◽  
pp. 2369-2373
Author(s):  
Juyeol Lee ◽  
Jihun Kang ◽  
Sukhyun Lee ◽  
Young Ho Rhee
Keyword(s):  
Total Synthesis ◽  
Metal Catalysis ◽  
Natural Analogues

scholarly journals The Combined Effect of Branching and Elongation on the Bioactivity Profile of Phytocannabinoids. Part I: Thermo-TRPs

Biomedicines ◽  
2021 ◽  
Vol 9 (8) ◽  
pp. 1070
Author(s):  
Daiana Mattoteia ◽  
Aniello Schiano Moriello ◽  
Orazio Taglialatela-Scafati ◽  
Pietro Amodeo ◽  
Luciano De Petrocellis ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Total Synthesis ◽  
Inflammatory Diseases ◽  
Alkyl Substituent ◽  
Binding Modes ◽  
Metabotropic Receptors ◽  
Inflammatory Agent ◽  
Structure Activity ◽  
Natural Analogues ◽  
Bioactivity Profile

The affinity of cannabinoids for their CB1 and CB2 metabotropic receptors is dramatically affected by a combination of α-branching and elongation of their alkyl substituent, a maneuver exemplified by the n-pentyl -> α,α-dimethylheptyl (DMH) swap. The effect of this change on other cannabinoid end-points is still unknown, an observation surprising since thermo-TRPs are targeted by phytocannabinoids with often sub-micromolar affinity. To fill this gap, the α,α-dimethylheptyl analogues of the five major phytocannabinoids [CBD (1a), Δ8-THC (6a), CBG (7a), CBC (8a) and CBN (9a)] were prepared by total synthesis, and their activity on thermo-TRPs (TRPV1-4, TRPM8, and TRPA1) was compared with that of one of their natural analogues. Surprisingly, the DMH chain promoted a shift in the selectivity toward TRPA1, a target involved in pain and inflammatory diseases, in all investigated compounds. A comparative study of the putative binding modes at TRPA1 between DMH-CBC (8b), the most active compound within the series, and CBC (8a) was carried out by molecular docking, allowing the rationalization of their activity in terms of structure–activity relationships. Taken together, these observations qualify DMH-CBC (8b) as a non-covalent TRPA1-selective cannabinoid lead that is worthy of additional investigation as an analgesic and anti-inflammatory agent.

scholarly journals Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

2016 ◽  
Vol 12 ◽  
pp. 1000-1039 ◽  
Author(s):  
Bin Yu ◽  
Hui Xing ◽  
De-Quan Yu ◽  
Hong-Min Liu
Keyword(s):  
Clinical Trials ◽  
Natural Products ◽  
Drug Discovery ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Biological Activities ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric

Oxindole scaffolds are prevalent in natural products and have been recognized as privileged substructures in new drug discovery. Several oxindole-containing compounds have advanced into clinical trials for the treatment of different diseases. Among these compounds, enantioenriched 3-hydroxyoxindole scaffolds also exist in natural products and have proven to possess promising biological activities. A large number of catalytic asymmetric strategies toward the construction of 3-hydroxyoxindoles based on transition metal catalysis and organocatalysis have been reported in the last decades. Additionally, 3-hydroxyoxindoles as versatile precursors have also been used in the total synthesis of natural products and for constructing structurally novel scaffolds. In this review, we aim to provide an overview about the catalytic asymmetric synthesis of biologically important 3-substituted 3-hydroxyoxindoles and 3-hydroxyoxindole-based further transformations.

Catalytic approaches to assemble cyclobutane motifs in natural product synthesis

2018 ◽  
Vol 5 (2) ◽  
pp. 254-259 ◽  
Author(s):  
Meng Wang ◽  
Ping Lu
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Total Synthesis ◽  
Natural Product ◽  
Transition Metal Catalysis ◽  
Natural Product Synthesis ◽  
Metal Catalysis ◽  
New Strategies

New strategies based on transition-metal catalysis or organocatalysis have provided new perspectives into the total synthesis of cyclobutane-containing natural products.

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