scholarly journals Back Cover: Flexible Total Synthesis of 11‐Deoxylandomycins and Their Non‐Natural Analogues by Way of Asymmetric Metal Catalysis (Angew. Chem. Int. Ed. 6/2020)

2020 ◽  
Vol 59 (6) ◽  
pp. 2524-2524
Author(s):  
Juyeol Lee ◽  
Jihun Kang ◽  
Sukhyun Lee ◽  
Young Ho Rhee
Keyword(s):  
Total Synthesis ◽  
Metal Catalysis ◽  
Back Cover ◽  
Natural Analogues

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 Back Cover: Total Synthesis of (−)‐Salinosporamide A via a Late Stage C−H Insertion (Angew. Chem. Int. Ed. 30/2019)

2019 ◽  
Vol 58 (30) ◽  
pp. 10376-10376
Author(s):  
Hadi Gholami ◽  
Aman Kulshrestha ◽  
Olivia K. Favor ◽  
Richard J. Staples ◽  
Babak Borhan
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Back Cover ◽  
Salinosporamide A

scholarly journals Back Cover: A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (−)-Thebaine (Angew. Chem. Int. Ed. 34/2018)

2018 ◽  
Vol 57 (34) ◽  
pp. 11080-11080
Author(s):  
Alexander Lipp ◽  
Dorota Ferenc ◽  
Christoph Gütz ◽  
Mario Geffe ◽  
Nina Vierengel ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Back Cover

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.

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