Jachak, Gorakhnath R. ; Athawale, Paresh R. ; Agarwal, Heena ; Barthwal, Manoj Kumar ; Lauro, Gianluigi ; Bifulco, Giuseppe ; Reddy, D. Srinivasa (2018) Total synthesis of the potent anti-inflammatory natural product solomonamide A along with structural revision and biological activity evaluation Organic and Biomolecular Chemistry, 16 (47). pp. 9138-9142. ISSN 1477-0520
Full text not available from this repository.
Official URL: http://doi.org/10.1039/C8OB02713G
Related URL: http://dx.doi.org/10.1039/C8OB02713G
Abstract
Herein, we report total synthesis of solomonamide along with its structural revision for the first time. The natural product possesses very potent anti-inflammatory activity and it contains a macrocylic peptide having four consecutive stereocenters on unnatural amino acid component. Key features in present synthesis include the application of an Evans aldol reaction, ligand free Heck macrocylization and chemo-selective oxidations. The challenging task of fixing the stereochemistry of OH at C5-position was accomplished with the help of DFT calculations, applying a quantum-mechanical (QM)/NMR combined approach. Biological evaluation in mouse paw edema model revealed that low dose (0.3 mg/kg) of synthesized solomonamide A showed 74% reduction at 6 h which was comparable to high dose (10 mg/kg) standard drug dexamethasone effect (75% at 6h). Thus, we further confirmed the revised structure of solomonamide A
Item Type: | Article |
---|---|
Source: | Copyright of this article belongs to The Royal Society of Chemistry |
ID Code: | 121846 |
Deposited On: | 22 Jul 2021 14:29 |
Last Modified: | 22 Jul 2021 14:29 |
Repository Staff Only: item control page