Chinese Journal of Chemistry

The cover picture shows the discovery of inhibitors targeting HIV-1 integrase-human LEDGF/p75 interaction via virtual screening. One of the most challenges for anti-HIV therapy is the rapid emergence of drug resistance. Protein-protein interaction inhibitors bring us hopes to overcome the viral resistance. We conducted a virtual screening combined with bioassays to search such inhibitors from natural product library. Several compounds were discovered to block integrase- LEDGF/p75 interaction with potent activities. These findings could be helpful for anti-HIV drug discovery. More details are discussed in the article by Tang et al. on page 2752–2758.

Nitrogen-containing heterocyclic compounds are important motifs of pharmaceuticals and functional materials, and there has been a growing interest in new synthetic methods for their preparations. In this paper, we report a direct cross-coupling reaction of indole with N-aryl tetrahydroisoquinolines in the presence of gold catalyst. The reaction is compatible with a wide range of substituted indoles, to enable the formation of various alkylated heteroarenes under very mild reaction conditions.

A series of 2-polyfluoroaryl arylacetates were synthesized by a one-pot three-component VNS_Ar-S_NAr reaction of polyfluoroarenes, ethyl 2-chloropropionate, and ortho-substituted nitrobenzenes.

Natural products were virtually screened against the LEDGF/p75 binding pocket of HIV-1 IN. Bioassays characterized 8 of 24 selected natural products as potent inhibitors. The two most potent inhibitors had IC₅₀ values of 0.56 and 0.69 µmol/L, respectively.

All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-1-ene-carboxylate (1a–1d) are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abundant (−)-shikimic acid (2) via cyclic sulfite intermediates are described in this article. The compound (3R,4R,5S)-1a was synthesized via four steps from (−)-shikimic acid in 79% overall yield. The compounds (3S,4R,5S)-1b, (3S,4S,5R)-1c and (3R,4S,5R)-1d were synthesized via seven steps from (−)-shikimic acid in 56%, 64% and 65% overall yields, respectively.

The gem-difluoromethylenated acetonide was efficiently synthesized as new precursor of HMG-CoA reductase inhibitor. Straightforward olefination via Pd-catalyzed C⁴-H activation of 1,3,5-trisubstituted pyrazoles was proceeded smoothly in the presence of Pd(OAc)₂ and AgCO₃.

A new and facile two-step synthetic strategy was developed to prepare magnetic Fe₃O₄ modified single crystalline up-conversion luminescent NaYF₄: Yb³⁺, Er³⁺ nanocrystals using Fe₃O₄ nanoparticles as the seeds. Acting as the "nuclei" in the reaction, the presence of Fe₃O₄ nanoparticles facilitates the formation of up-conversion NaYF₄: Yb³⁺, Er³⁺ nanocrystals on their surfaces through heterogeneous nucleation process. The uptake and intracellular distribution of as-prepared multifunctional nanocrystals were also investigated in cell-labelling.

A novel class of organic D-π-A dyes employing tri(triphenylamine)-substituted styrene as donor was designed and synthesized for dye-sensitized solar cells (DSSCs). The DSSC device based on TF with furan as π-linker achieved a solar-to-electricity conversion efficiency (η) of 4.52%.

A highly efficient method for readily preparing 4,5-disubstituted 2H-1,2,3-triazoles was found. Under ambient conditions, a catalyst free cycloaddition between substituted vinyl sulfones and sodium azide could be completed in a very short time. In this cycloaddition process, sulfonyl group acts as a leaving group, while its ester group was retained.

Eight peptoid chiral stationary phases (CSPs) terminated with L-proline or L-leucine amide were prepared and evaluated with 59 racemates. The influence of terminal p-methyl and p-chloro substituents on selectivity was found varied along with the terminal amino acid and peptoid chain length.

Z and E configuration 4-aryl-but-2-en-1-ols were isolated from several terrestrial plants, and (Z)-4-aryl-but-2-en-1-ols were found to have choleretic activity. Strategies have been reported to synthesize (E)-4-aryl-but-2-en-1-ols with high selectivity. However, there is no method to obtain (Z)-4-aryl-but-2-en-1-ols with high selectivity now. We developed a Suzuki-Miyaura cross-coupling reaction of 1,2-oxaborol-2(5H)-ols with benzyl bromides to synthesize (Z)-4-aryl-but-2-en-1-ols, the products were obtained in up to 94% isolated yield.

The nanoporous carbon/graphene composite (NCGC) has been prepared through a one pot hydrothermal method by using graphene oxide (GO) as raw material, phenol, formaldehyde as carbon resources and triblock copolymer F127 as template. Pt electrocatalyst taking NCGC as support shows better activity and stability than that with XC-72 as support toward methanol oxidation.

An eight-step synthetic route was developed to synthesize a series of nicotine analogs. 17 nicotine analogs were synthesized, among which compounds 10d and 10g exhibited excellent biological activities toward SY-SY5Y and RD.

Water-soluble diol-functionalized imidazolium ionic liquid 1, prepared from 2,2-bis(1-methyl-methylimidazolium)propane-1,3-diol bromide, potassium hydroxide, and malononitrile, was used as an efficient phosphine-free ligand for palladium-catalyzed arylation of aryl halides with acrylates in aqueous phase under mild conditions.

A novel colorimetric chemosensor PBIOSi had been designed and synthesized. The addition of F− to a THF solution of PBIOSi resulted in an obvious color change (from red to green) in a short time because of the specific cleavage of SiO bond in PBIOSi by F−.

Ethylenediamine (H₂NCH₂CH₂NH₂) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1–2 mol% of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3–10 h efficiently afforded various aryl nitroalkenes 1a–1y in 85%–97% yields.

A facile iron-catalyzed C(sp³)-C(sp²) bond formation through DDQ-mediated cross-dehydrogenative homo-coupling of (E)-1,2-diarylprop-1-enes for the synthesis of highly aryl-substituted cyclopentenes has been developed.

An in situ wet cell TEM set up was used to observe electrochemical deposition of nano nickel film in liquid. Interestingly, nickel particle and particle layers appeared in front of the film first and then merged with it.

Fe₃O₄@SiO₂-NH₂ nano-carrier particles with chain structure were successfully prepared. Immobilization of laccase using Fe₃O₄@SiO₂-NH₂ as carrier through covalent attachment was carried out. The optimal conditions regarding degradation efficiency was discussed. Magnetic nanoparticles immobilized laccase was easy to operate, separate and recover from the reaction system. Moreover, because of its magnetic, catalytic, and other good characteristics, the immobilized laccase had a faster degradation rate than the free laccase by the "magneto-induced effect" on the laccase; the magnetic carrier Fe₃O₄@MSS-NH₂ could promote the degradation reaction and the activity of immobilized laccase was kept almost unchanged during the course of repeated use.

According to the different desilylation conditions of trimethylsilyl group and Si(CH₃)₂ group in silacyclopentadiene unit, aryleneethynylenesiloles dendron was synthesized.

The monolayer technique combined with atomic force microscopy (AFM) was used to probe the interfacial behavior of DMPC and surfactin-C16 in the mixed monolayer. The two components are partially miscible in some cases. It is proposed that the miscibility is governed by hydrophobic interactions between surfactin-C16 and DMPC, and the ionization states and physical states of surfactin-C16 in the monolayer.

New C3,4-disubstituted bis-triazolyl glycoligands that feature a glucosyl or galactosyl scaffold incorporating dual pyrenyl groups were synthesized via the Cu^I-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (Cue-AAC). These compounds exert a major emission band corresponding to that of pyrene excimer and respond specifically to mercury with a markedly quenched fluorescence. The epimeric nature of the pyranoglycosyl scaffold is determined influential toward the selectivity of the sensors.