Multicomponent one-pot Biginelli reactions have been successfully performed using vegetable oil as bio-based, non-toxic, and environmentally friendly solvents. Palm oil was demonstrated to be a highly effective greener solvent as...
The
development of safer and more sustainable solvents is an important
discipline in the context of stricter regulations and environmental
protection. This work demonstrates the sustainable synthesis of a
potentially bio-based, inherently nonperoxide-forming ether solvent,
namely, 2,5-diethyl-2,5-dimethyloxolane (DEDMO), in quantitative yields
with high atom economy (97%) and reaction mass efficiency (94%) from
renewable sources. Quantum mechanical calculations of theoretical
NMR chemical shifts and DP4+ probability modeling indicated that the cis isomer of DEDMO was most plausible (with a probability
value of 99.98%); however, the actual NMR data suggested a 1:1 mixture
of cis and trans isomers for DEDMO.
The solvation properties of DEDMO have also been evaluated using Kamlet–Abboud–Taft
(KAT) parameters, Hansen solubility parameters (HSPs), and in
silico modeling COSMO-RS. The KAT parameter
relating to a combined effect of solvent polarity and polarizability
(π*) was 0.32 for DEDMO, which was lower than other quaternary
ethers such as 2,2,5,5-tetramethyloxolane (TMO) (0.35) and cineole
(0.41). In silico COSMO-RS modeling suggested that
DEDMO has similar characteristics to hydrocarbon solvents such as n-hexane or toluene. The substitution of all hydrogen atoms
at the α-position to the ethereal oxygen with an alkyl group,
such as the methyl and ethyl groups of DEDMO, inhibits its ability
to form explosive peroxides. Moreover, the steric concealment of the
ethereal oxygen of DEDMO leads to similar properties to hydrocarbon
solvents rather than traditional ether solvents. The performance of
DEDMO as a solvent is demonstrated in an enzymatic esterification,
as well as heterocyclic synthesis by means of a Biginelli reaction,
and annulation reactions. Application testing of DEDMO revealed that
its behavior was similar in solvent properties to hydrocarbon solvents;
in fact, results were typically between those of toluene and n-hexane. The presence of ethyl groups enhances its nonpolar
character, and as such, DEDMO was demonstrated to perform better than
the green quaternary ethers TMO in some reactions. Preliminary in silico toxicity predictions indicate that DEDMO is nonmutagenic,
and thus DEDMO is a potentially green hindered ether solvent for the
substitution of conventional nonpolar solvents.
A new cyclic pentapeptide, pentaminolarin (1), and a new cytochalasin, xylochalasin (2), along with thirteen known compounds (3-15) were isolated from the wood-decaying fungus Xylaria sp. SWUF08-37. The absolute configurations of 1 were determined by a combination of Marfey's method and TDDFT ECD calculation and the absolute configurations of 2 were established by TDDFT ECD calculation. Compound 12 showed moderate cytotoxicity against HeLa (IC 50 = 19.60 µg/mL), HT29 (IC 50 = 17.31 µg/mL), HCT116 (IC 50 = 14.28 µg/mL), MCF-7 (IC 50 = 15.38 µg/mL), and Vero (IC 50 = 24.97 µg/mL) cell lines by MTT assay. Compounds 1 and 2 showed slight cytotoxicity against all tested cancer cell lines.
Highly effective acid catalysed reactions of amines with dimethyl carbonate (DMC) have been conducted, with significant yields and selectivity towards carboxymethylation or methylation products. Lewis acids (FeCl3, ZnCl2, and AlCl3.6H2O),...
A new cerebroside, namely allantoside (1), and 10 known compounds (2-11) were isolated from Xylaria allantoidea SWUF76. The structure of compound 1 was determined by comprehensive spectroscopic analysis including 1D and 2D nuclear magnetic resonance (NMR) as well as high-resolution electron ionisation mass spectrometry (HREIMS) and electrospray ionisation mass spectrometry (ESIMS). Compounds 1, 4, 5, 6, 7, 8 and 11 were evaluated for cytotoxic activities against cancer cell lines (Hela, HT29, HCT116 and MCF-7) and normal Vero cell lines by MTT assay. Compounds 6 and 7 exhibited anticancer activity after 24 h of treatment. Compound 7 showed significant cytotoxicity against Hela (IC = 2.24 μg/mL), HT29 (IC = 2.51 μg/mL), HCT116 (IC = 3.50 μg/mL) and MCF-7 (IC = 3.77 μg/mL) and Vero (IC:3.65 μg/mL) cells. Compound 6 showed slight cytotoxicity against all tested cancer cell lines.
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