Abstract：
:A concise total synthesis of an exceedingly potent anti-inflammatory agent violacin A as well as the preparation of thirty analogues of this lead from commercially available orcinol are described. Highlights of our synthetic efforts involve Friedel-Crafts acylation, the regioselective etherification and esterification of phenolic hydroxyl groups, and Baker-Venkatamaran rearrangement to form basic skeleton of violacin A. The deprotection reaction with Pd-catalytic was involved to avoid the elimination of the hemiacetal hydroxyl at C2. In addition, all synthetic compounds were screened for anti-inflammatory activity against nitric oxide (NO) production using lipopolysaccharide (LPS)-induced Raw264.7 cells. A range of violacin A derivatives 11b, 11d, 11f, 12e, 12g, 13g, 17d-g exhibited stronger anti-inflammatory effect than that of violacin A. Notably, halogeno-benzyloxy substituent at C-7 were favourable for anti-inflammatory activities of violacin A derivatives. Additionally, Western blot results indicated halogeno-benzyloxy derivatives inhibited pro-inflammatory cytokines releases correlated with the suppression of NF-κB signaling pathway.
journal_name
Bioorg Chemjournal_title
Bioorganic chemistryauthors
Liu Q,Mu Y,An Q,Xun J,Ma J,Wu W,Xu M,Xu J,Han L,Huang Xdoi
10.1016/j.bioorg.2019.103420subject
Has Abstractpub_date
2020-01-01 00:00:00pages
103420eissn
0045-2068issn
1090-2120pii
S0045-2068(19)31211-8journal_volume
94pub_type
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