325151-61-9Relevant academic research and scientific papers
A short and efficient total synthesis of the bromotyrosine-derived alkaloid psammaplysene A
Xu, Jingjing,Wang, Kai,Wu, Jinlong
, p. 13747 - 13749 (2018/04/25)
Psammaplysene A, an inhibitor of FOXO1a-mediated nuclear export, has been synthesized by a concise and improved route from tyrosine-derived acid and amine fragments which were easily constructed using commercially available p-hydroxybenzaldehyde and tyramine as starting material, respectively. The strategy provides an efficient access of psammaplysene analogues that can be explored for potential pharmaceutical or biological activities.
Synthetic analogs of stryphnusin isolated from the marine sponge: Stryphnus fortis inhibit acetylcholinesterase with no effect on muscle function or neuromuscular transmission
Moodie, Lindon W. K.,?u?ek, Monika C.,Frange?, Robert,Andersen, Jeanette H.,Hansen, Espen,Olsen, Elisabeth K.,Cergolj, Marija,Sep?i?, Kristina,Hansen, Kine ?.,Svenson, Johan
, p. 11220 - 11229 (2016/12/07)
The marine secondary metabolite stryphnusin (1) was isolated from the boreal sponge Stryphnus fortis, collected off the Norwegian coast. Given its resemblance to other natural acetylcholinesterase antagonists, it was evaluated against electric eel acetylcholinesterase and displayed inhibitory activity. A library of twelve synthetic phenethylamine analogs, 2a-7a and 2b-7b, containing tertiary and quaternary amines respectively were synthesized to investigate the individual structural contributions to the activity. Compound 7b was the strongest competitive inhibitor of both acetylcholinesterase and butyrylcholinesterase with IC50 values of 57 and 20 μM, respectively. This inhibitory activity is one order of magnitude higher than the positive control physostigmine, and is comparable with several other marine acetylcholinesterase inhibitors. The physiological effect of compound 7b on muscle function and neuromuscular transmission was studied and revealed a selective mode of action at the investigated concentration. This data is of importance as the interference of therapeutic acetylcholinesterase inhibitors with neuromuscular transmission can be problematic and lead to unwanted side effects. The current findings also provide additional insights into the structure-activity relationship of both natural and synthetic acetylcholinesterase inhibitors.
Aplysamine-1 and related analogs as histamine H3 receptor antagonists
Swanson, Devin M.,Wilson, Sandy J.,Boggs, Jamin D.,Xiao, Wei,Apodaca, Richard,Barbier, Ann J.,Lovenberg, Timothy W.,Carruthers, Nicholas I.
, p. 897 - 900 (2007/10/03)
Aplysamine-1 (1), a marine natural product, was synthesized and screened for in vitro activity at the human and rat histamine H3 receptors. Aplysamine-1 (1) was found to possess a high binding affinity for the human H3 receptor (Ki = 30 ± 4 nM). Synthetic analogs of 1, including des-bromoaplysamine-1 (10) and dimethyl-{2-[4-(3-piperidin-1-yl- propoxy)-phenyl]-ethyl}-amine (13), were potent H3 antagonists.
Turbotoxins A and B, novel diiodotyramine derivatives from the Japanese gastropod Turbo marmorata
Kigoshi, Hideo,Kanematsu, Kengo,Yokota, Kyoko,Uemura, Daisuke
, p. 9063 - 9070 (2007/10/03)
Bioassay-guided separation of the aqueous ethanol extract of the viscera of the Japanese gastropod Turbo marmorata resulted in the isolation of two toxins, turbotoxins A and B. Their structures were determined by spectral analysis and confirmed by organic synthesis to be diiodotyramine derivatives. Turbotoxins A and B exhibited acute toxicity against ddY mice, with LD99 values of 1.0 and 4.0 mg/kg, respectively. The structure-toxicity relationships of turbotoxins were examined, and it was proved that the iodine atoms and trimethylammonium groups are important for its acute toxicity. Turbotoxin A inhibits acetylcholinesterase with an IC50 of 28 μM. (C) 2000 Elsevier Science Ltd.
