76252-28-3Relevant academic research and scientific papers
Euodenine A: A small-molecule agonist of human TLR4
Neve, Juliette E.,Wijesekera, Hasanthi P.,Duffy, Sandra,Jenkins, Ian D.,Ripper, Justin A.,Teague, Simon J.,Campitelli, Marc,Garavelas, Agatha,Nikolakopoulos, George,Le, Phuc V.,De A. Leone, Priscila,Pham, Ngoc B.,Shelton, Philip,Fraser, Neil,Carroll, Anthony R.,Avery, Vicky M.,McCrae, Christopher,Williams, Nicola,Quinn, Ronald J.
, p. 1252 - 1275 (2014/03/21)
A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-κB reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-α, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.
Ultrasound-assisted convenient synthesis of hypolipidemic active natural methoxylated (E)-arylalkenes and arylalkanones
Joshi, Bhupendra P.,Sharma, Anuj,Sinha, Arun K.
, p. 3075 - 3080 (2007/10/03)
An ultrasound-assisted convenient method was developed for the conversion of toxic methoxylated cis-isomer of arylalkenes into its hypolipidemic active trans-isomer. Treatment of cis-isomer or mixture of all three isomers (1a-1j) with ammonium formate and 10% Pd/C gave arylalkanes (2a-2j), which upon oxidation with DDQ in anhydrous dioxane containing a little amount of silica gel, provided (E)-arylalkenes (3a-3g) in 42-72% yield depending upon the substituents attached at the aryl ring. The same method, upon addition of a few drops of water, provided hypolipidemic active arylalkanones (3h-3j) in 59-65% yield.
An effective system to synthesize hypolipidemic active α-asarone and related methoxylated (E)-arylalkenes
Sharma, Anuj,Joshi, Bhupendra P.,Sinha, Arun K.
, p. 2231 - 2235 (2007/10/03)
Methoxylated (E)-arylalkenes (1a-1k) were prepared in two steps by an improved Grignard reaction comprising the reverse addition of alkylmagnesium bromide to benzaldehydes (2a-2k) in anhydrous ether and toluene into arylalkanols (3a-3k) in high yield, followed by dehydration with silica gel under microwave irradiation for 3-12 min, depending upon the substituents attached to the aromatic ring to afford hypolipidemic active α-asarone (1a) and related methoxylated (E)-arylalkenes (1b-1k).
One-pot synthesis of trans-β-alkylstyrenes
Liu, Ju-Tsung,Yao, Ching-Fa
, p. 6147 - 6150 (2007/10/03)
One-pot synthesis of (E)-alkenes 5 from the reactions of aldehyde 1 and nitromethane 2 in the acetic acid solution and then with triethylborane 4 in the biphase of diethyl ether and aqueous solution in the presence of oxygen in air was reported. Various (E)-alkenes 7 could also be prepared when different kinds of secondary or tertiary alkyl iodides 6 were used under similar conditions.
Pharmacology on rat ileum of certain 2-substituted 3-(dimethylamino)-5,6-dimethoxyindenes related to 5,6-(methylenedioxy)indene calcium antagonists
Witiak,Kakodkar,Brunst,Baldwin,Rahwan
, p. 1313 - 1315 (2007/10/06)
Whereas the 2-propyl- and 2-butyl-5,6-(methylenedioxy)indene caclium antagonists reversed the spasmogenic action of several agonists including PGF(2α) and acetylcholine at 5 x 10-5 to 10-4 M on the rat ileum, the corresponding 5,6-dimethoxy analogues exhibited spasmogenic activity at higher concentration (10-4-10-3 M) and exhibited neither spasmogeric nor spasmolytic activity at lower (10-6-10-5 M) concentration. The results are compared to the methyl and 2-ethyl analogues. At 10-4 M only the butyl analogue was capable of moderate antagonism of acetylcholine and at 10-3 M all four analogues were capable of moderately antagonizing the actions of acetylcholine.
