79672-56-3Relevant articles and documents
Design, Synthesis, Structure-Activity Relationship and Docking Studies of Novel Functionalized Arylvinyl-1,2,4-Trioxanes as Potent Antiplasmodial as well as Anticancer Agents
Agrawal, Prakhar,Chaudhary, Sandeep,Coghi, Paolo,Jun Yang, Li,Kam Wai Wong, Vincent,Peng, Yuzhong,Sahal, Dinkar,Sharma, Richa,Shyamlal, Bharti Rajesh K.,Tiwari, Mohit K.,Yadav, Dharmendra K.,Yadav, Lalit
, (2020/06/09)
A novel series of synthetic functionalized arylvinyl-1,2,4-trioxanes (8 a–p) has been prepared and assessed for their in vitro antiplasmodial activity against the chloroquine-resistant Pf INDO strain of Plasmodium falciparum by using a SYBR green-I fluorescence assay. Compounds 8 g (IC50=0.051 μM; SI=589.41) and 8 m (IC50=0.059 μM; SI=55.93) showed 11-fold and >9-fold more potent antiplasmodial activity, respectively, as compared to chloroquine (IC50=0.546 μM; SI=36.63). Different in silico docking studies performed on many target proteins revealed that the most active arylvinyl-1,2,4-trioxanes (8 g and 8 m) showed dihydrofolate reductase (DHFR) binding affinities on a par with those of chloroquine and artesunate. The in vitro cytotoxic potentials of 8 a–p were also evaluated against human lung (A549) and liver (HepG2) cancer cell lines along with immortalized normal lung (BEAS-2B) and liver (LO2) cell lines. Following screening, five derivatives viz. 8 a, 8 h, 8 l, 8 m and 8 o (IC50=1.65–31.7 μM; SI=1.08–10.96) were found to show potent cytotoxic activity against (A549) lung cancer cell lines, with selectivity superior to that of the reference compounds artemisinin (IC50=100 μM), chloroquine (IC50=100 μM) and artesunic acid (IC50=9.85 μM; SI=0.76). In fact, the most active 4-naphthyl-substituted analogue 8 l (IC50=1.65 μM; SI >10) exhibited >60 times more cytotoxicity than the standard reference, artemisinin, against A549 lung cancer cell lines. In silico docking studies of the most active anticancer compounds, 8 l and 8 m, against EGFR were found to validate the wet lab results. In summary, a new series of functionalized aryl-vinyl-1,2,4-trioxanes (8 a–p) has been shown to display dual potency as promising antiplasmodial and anticancer agents.
Metal chloride-promoted aldol reaction of α-dimethylsilylesters with aldehydes, ketones, and α-enones
Miura, Katsukiyo,Nakagawa, Takahiro,Hosomi, Akira
, p. 1917 - 1921 (2007/10/03)
In the presence of a catalytic amount of LiCl, α-dimethylsilylesters (α-DMS-esters) 1 smoothly reacted with various aldehydes at 30°C to give aldols in good to high yields. On the other hand, the aldol reaction with ketones was effectively promoted by MgCl2 rather than by LiCl. α-Enones also underwent the metal chloride-promoted addition of 1 at the carbonyl carbon or β-carbon. Georg Thieme Verlag Stuttgart.
Convenient access to 4,4-disubstituted 4H-chromenes. Synthesis of 4-methyl-4-(4-methoxyphenyl)-benzo[h]-4H-chromene
De Keukeleire,Saeyens
, p. 4397 - 4402 (2007/10/03)
4-Methyl-4-(4-methoxyphenyl)-benzo[h]-4H-chromene is synthesised by condensation of 4-methoxyacetophenone and ethyl acetate in strong base, followed by coupling with 1-naphthol, reduction to the epimeric lactols and elimination of water.
