6413-10-1Relevant articles and documents
Synthesis, activity and mechanism for double-ring conjugated enones
Chen, Guangying,Huang, Gangliang,Liu, Jian,Zhou, Shiyang
, (2021)
The relationship between TLR4 and inflammation-related diseases has been paid more and more attention. The studies have shown that TLR4/NF-κB signaling pathway plays an important role in the transmission of inflammatory signals. A large number of pro-inflammatory factors, chemokines, adhesion factors, TLR4 and its ligands interact with each other, and jointly promote the development of diseases. In this work, 8 target compounds were synthesized to screen the inhibitory activity of TLR4 in vitro. The results of TLR4 inhibition test in vitro showed that the double-ring conjugated enones had a good inhibitory activity, and the IC50 value of compound 4f was 0.56 ± 0.10 μM, and it was superior to the positive control methotrexate. To further study the anti-inflammatory effect and mechanism of double-ring conjugated enones by using LPS induced rat synovial cell inflammation model. The results of the mechanism test showed that compound 4f could effectively promote the apoptosis of rat synovial cells, and the mechanism might be related to the up-regulation of the expression of apoptosis-related protein Caspase-3. In addition, compound 4f could significantly inhibit the increase of inflammatory factors TNF-α, IL-1β and IL-6 in rat synovial cells induced by LPS, showing a good anti-inflammatory activity. In the TLR4/NF-κB signaling pathway test of rat synovial cells, compound 4f can effectively regulate the expression levels of TLR4, MyD88, NF-κB and IκB related proteins in TLR4/NF-κB signaling pathway, which may be due to its inhibition of LPS-induced inflammation in rat synovial cells. At the same time, it inhibits the abnormal proliferation of cells and its important mechanism promoted of apoptosis.
Design, synthesis and anti-rheumatoid arthritis evaluation of double-ring conjugated enones
Zhou, Shiyang,Zou, Huiying,Huang, Gangliang,Chen, Guangying,Zhou, Xueming,Huang, Shuheng
, (2021/02/22)
Four series of double-ring conjugated enones were designed, synthesized and studied for the inhibition of synovial cell activity through the modification of Dysodensiol K core structure, double-ring, double-bond and double-carbonyl groups. For in vitro synovial cell assay of rats, compound 151 and 168 exhibited good inhibitory activities, with IC50 values of 2.71 ± 0.18 and 2.68 ± 0.16 μM respectively. At the same time, the LDH release and LD50 test results revealed that the target compounds were low cytotoxicity and acute toxicity. For in vivo CIA model test through the oral administration, compounds 151 and 168 were exhibited similar effect to positive control group methotrexate.
Br?nsted acidic cellulose-PO3H: An efficient catalyst for the chemoselective synthesis of fructones and trans-esterification via condensation of acetoacetic esters with alcohols and diols
Naikwadi, Dhanaji R.,Singh, Amravati S.,Biradar, Ankush V.
, (2021/10/04)
Cellulose is the most abundant organic source and has expedient a great deal of interest as renewable and emerged as sustainable feedstock. The functionalization of cellulose as designed catalytic system intriguing furnished to the production of fine chemicals. Herein, we synthesized an environmental friendly solid acid catalyst by functionalizing cellulose with phosphoric acid (PO3H). The successful functionalization of cellulose with PO3H was confirmed by 31P NMR, ICP-OES, FE-SEM, and XPS analysis. ICP-OES revealed the presence of phosphorus content of ～1.0 wt. % on the catalyst's surface while elemental mapping by FESEM and XPS shows a uniform distribution of phosphorus over the material. The synthesized solid acid catalyst was utilized for condensation of diols with acetoacetic esters in solvent-free conditions to synthesize fine chemicals. The present approach not only circumvented the one-step protection and other products but more fascinatingly provided trans-esterification of acetoacetic esters with diols and n-alcohols. The catalyst was successfully used for chemoselective protection on ethyl acetoacetate with 1, 2 diols to essential fructone molecule with ～100% conversion and 99% selectivity. The results suggested that the catalyst has the advantage over commercial solid acid heterogeneous and homogeneous catalysts.
