Background:
Effective new anti-human cytomegalovirus (HCMV) agents and regimens need to be developed. We examined the anti-HCMV properties of crude extract (True World Extract of Bambuseae sasa [TWEBS]) and five compounds (p-coumaric acid, 3-hydroxy-4-methoxyben-zaldehyde [vanillin], p-hydroxybenzaldehyde, 3-hydroxypyridine and 4',5,7-trihydroxy-3',5'-dimethoxyflavone [tricin]), isolated from Sasa albo-marginata, a bamboo known in Japan as Sasa.
Methods:
Among TWEBS and five compounds screened in a plaque reduction assay, four showed anti-HCMV activity in the MRC-5 human embryonic fibroblast cell line. The anti-HCMV mechanisms of the TWEBS was examined by western blot analysis using primary antibody specific for an immediate early (IE) antigen of HCMV, for a structural late antigen of HCMV and for β-actin.
Results:
Treatment of cells with ⩾0.001% of TWEBS inhibited the observable cytopathic effects of HCMV on infected cells. Western blot analysis demonstrated that TWEBS decreased the expression of IE antigen and late antigen of HCMV in the infected cells. Next, we examined the anti-HCMV properties of five compounds isolated from TWEBS. In a viral plaque reduction assay, tricin showed dose-dependent inhibitory properties with a 50% effective concentration of 0.17 µug/ml (selective index =1,205.8).
Conclusions:
The hot water extract (TWEBS) of Sasa albo-marginata, with tricin isolated from it, has anti-HCMV activity in MRC-5 cells. TWEBS and/or tricin are a novel compound with potential anti-HCMV activity. Future studies should evaluate these findings in vivo.
The rhodium(III)-catalyzed direct alkenylation of N-phenylindole-3-carboxylic acids with alkenes including acrylate ester, acrylamide, and acrylonitrile proceeds smoothly at the C4-position through regioselective C-H bond cleavage directed by the carboxyl group. In marked contrast, the indole substrates react with diarylacetylenes accompanied by cleavage of the C2-H and C2'-H bonds and decarboxylation to produce 5,6-diarylindolo[1,2- a]quinolone derivatives. DFT calculations have suggested that the smooth insertion of an alkene to a C4-rhodated six-membered metallacycle intermediate leads to the C4 alkenylated products, while the latter annulation at the C2- and C2'-positions is attributable to facile reductive elimination in the corresponding seven-membered metallacycles formed by the double C-H bond cleavage and alkyne insertion.
The rhodium(III)-catalyzed annulative coupling of 9-benzoylcarbazoles with internal alkynes proceeds efficiently through ortho C–H and C–N bond cleavages. This reaction provides direct access to variously substituted indanone derivatives. The carbazolyl leaving group can be readily recovered and reused for preparing the starting materials.
N-acylation reaction offers an opportunity to develop an efficient synthesis of amide group-containing molecules. We found that N-acyl carbazoles showed remarkable selectivity in transamidation. Sterically less hindered primary amines are selectively acylated with N-acyl carbazoles without any additives. Various functional groups such as alcohol, phenol, indole, and aniline moieties are tolerated under mild conditions. The synthetic utility was displayed in one-pot synthesis of an N-acyl polyamine natural product. The terminal amines of spermidine were selectively benzoylated with N-benzoyl carbazole, followed by acetylation reaction accomplished the total synthesis in a highly efficient manner.
The CÀ H alkenylation of N-acetylcarbazoles proceeds smoothly at the C1-position in the presence of a cationic Cp*Rh(III) catalyst to produce 1-alkenylcarbazoles. The use of a cationic Cp E Rh(III) catalyst enables further alkenylation to give 1,8-dialkenylcarbazoles. The direct alkenylation procedure in combination with the ready removal of the acetyl directing group provides a straightforward synthetic pathway to 1-and/or 8-alkenyl-N-H-carbazole derivatives. One of 1-alkenyl-N-H-carbazoles obtained by the present CÀ H alkenylation/deacetylation exhibits solvatochromism.
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