63353-50-4Relevant academic research and scientific papers
Biomimetic synthesis and anti-inflammatory evaluation of violacin A analogues
Wu, Wenxi,Mu, Yu,Liu, Bo,Wang, Zixuan,Guan, Peipei,Han, Li,Jiang, Mingguo,Huang, Xueshi
, (2021/04/23)
Violacin A, a chromanone derivative, isolated from a fermentation broth of Streptomyces violaceoruber, has excellent anti-inflammatory potential. Herein, a biogenetically modeled approach to synthesize violacin A and twenty-five analogues was described, which involved the preparation of aromatic polyketide precursor through Claisen condensation and its spontaneous cyclization. The inhibitory effect on nitric oxide (NO) production of all synthetic molecules was evaluated by lipopolysaccharide (LPS)-induced Raw264.7 cells. The results revealed that introduction of aliphatic amine moieties on C-7 obviously improved the anti-inflammation effect of violacin A, and also the aromatic ether instead of ketone group at side chain was favorable to increase the activity. Among them, analogue 7a and 16d were screened as the most effective anti-inflammatory candidates. Molecular mechanism research revealed that 7a and 16d acquired anti-inflammatory ability due to the inhibition of NF-κB signaling pathway.
Cycloadditions, 12. - Influence of Aromatic Alkyl Groups on the Intramolecular Diels-Alder Reaction of Aryl Allenecarboxylates and of Allenecarboxanilides
Himbert, Gerhard,Fink, Dieter,Diehl, Klaus
, p. 431 - 442 (2007/10/02)
The aryl allenecarboxylates 4a-o and the allenecarboxanilides 9a, b, e, h, and l, which differ from one another only by the number or by the size of the alkyl groups attached to the arene, are synthesized by the ylide method via the appropriately substituted 2-halo-, 2-phosphonio-, and 2-phosphoranylideneacetic acid derivatives (1-->2-->3-->4 and 6-->7-->8-->9, resp.).By refluxing in xylene they are transformed into the tricyclic compounds 5 and 10; the rates and their differences are discussed.
