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Racemic new cyclohexenone and cyclopentenone derivatives, (±)-(4R*,5S*,6S*)-3-amino-4,5,6-trihydroxy-2-methoxy-5-methyl-2-cyclohexen-1-one (1) and (±)-(4S*,5S*)-2,4,5-trihydroxy-3-methoxy-4-methoxycarbonyl-5-methyl-2-cyclopenten-1-one (2), and two new xanthone derivatives 4-chloro-1,5-dihydroxy-3-hydroxymethyl-6-methoxycarbonyl-xanthen-9-one (3) and 2,8-dimethoxy-1,6-dimethoxycarbonyl-xanthen-9-one (4), along with one known compound, fischexanthone (5), were isolated from the culture of the mangrove endophytic fungus Alternaria sp. R6. The structures of these compounds were elucidated by analysis of their MS (Mass), one and two dimensional NMR (nuclear magnetic resonance) spectroscopic data. Compounds 1 and 2 exhibited potent ABTS [2,2′-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid)] scavenging activities with EC50 values of 8.19 ± 0.15 and 16.09 ± 0.01 μM, respectively. In comparison to Triadimefon, compounds 2 and 3 exhibited inhibitory activities against Fusarium graminearum with minimal inhibitory concentration (MIC) values of 215.52 and 107.14 μM, respectively, and compound 3 exhibited antifungal activity against Calletotrichum musae with MIC value of 214.29 μM.

A direct one-pot three-component reaction of 4-acetyl- N -benzylbenzamide, ethyl acetoacetate or methyl acetoacetate, and aromatic aldehydes under microwave irradiation afforded a series of new cyclo­hexenone derivatives. The proposed procedure has the advantages of one-pot reaction, high efficiency, short reaction time, and simple workup. The antimicrobial activity of the obtained cyclohexenone derivatives was tested against a variety of bacteria ( E. coli , S. aureus , S. pyogenes , P. aeruginosa ) and fungi ( C. albicans , A. niger , A. clavatus ).

We designed 21 ethyl 3,5-diphenyl-2-cyclohexenone-6-carboxylate derivatives to identify compounds exhibiting anticancer activity. To measure the inhibitory effects of the compounds on cancer cell growth, a long-term survival clonogenic assay was performed. Since compounds containing a cyclohexenone moiety inhibit the enzyme acetylcholinesterase, an in vitro acetylcholinesterase assay was performed for all 21 cyclohexenone derivatives. To examine the effect of the derivative that exhibited the best cancer cell growth inhibition on the induction of apoptosis by demonstrating the activation of caspases and apoptosis regulatory proteins, immunoblotting and immunofluorescence microscopic analyses were performed. The binding mode between the cyclohexenone derivatives and acetylcholinesterase was elucidated at the molecular level using in silico docking. Druggability was evaluated based on ligand efficiency.

A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr.

Toxicity studies were conducted to provide safety data of potential drug candidates by determining lethal and toxic doses. This study was designed for pre-clinical evaluation of novel cyclohexenone derivative with respect to the acute and sub-acute toxicity along with the diabetogenic potential. Acute and sub-acute toxicity were assessed after intraperitoneal (i.p) injection of the investigational compound through selected doses for 21 days. This was followed by assessment of isolated body organs (liver, kidney, heart and pancreas) via biochemical indicators and histopathological techniques. No signs of toxicity were revealed in the study of acute toxicity. Similarly, a sub-acute toxicity study showed no significant difference in biochemical indicators on 11th and 21st days between treated and control groups. However, in blood urea nitrogen (BUN) and random blood glucose/sugar (RBS) values, significant differences were recorded. Histopathological evaluation of liver, kidney, pancreas and heart tissues revealed mild to severe changes in the form of steatosis, inflammation, fibrosis, necrosis and myofibrillary damages on 11th and 21st days of treatment. In conclusion, the median lethal dose of the tested compound was expected to be greater than 500 mg/kg. No significant change occurred in selected biomarkers, except BUN and RBS levels, but a histopathological study showed moderate toxic effect on liver, kidney, pancreas and heart tissues by the cyclohexenone derivative.

A series of 2-oxo-N,4,6-triarylcyclohex-3-enecarboxamides were synthesized by condensing acetophenone and aromatic aldehydes with acetoacetanilide in ethanol in the presence of 2-hydroxyethylammonium acetate (2-HEAA) as a basic ionic liquid at ambient conditions. This process is simple, efficient and environmentally benign and proceeds in high yield, short reaction times and there is no need for column chromatography purification.

A high efficient and convenient one-pot three-component diastreoselective synthesis of polysubstituted cyclohexenones in excellent yields has been developed through Michael addition and Claisen–Schmidt condensation of aldehydes and acetophenone with 3-oxo-N-phenylbutanamide using piperidine as an effective reagent under mild conditions within sort reaction time without using any previous activation.

We used metabolic inhibitors and radiolabelled tracers to investigate the biosynthetic pathway for mycosporines (mycosporine-like amino acids) in the facultatively heterotrophic cyanobacterium (blue-green alga) Chlorogloeopsis sp. strain PCC 6912. 14 C-pyruvate was taken up and resulted in labelling of the core cyclohexenone, whereas feeding with 14 C-acetate did not label cyclohexenone, in spite of strong cellular uptake. In addition, mycosporine synthesis was depressed in the presence of externally administered tyrosine (5 mM), a known feedback inhibitor of the shikimic acid pathway in cyanobacteria. We thus conclude that the mycosporine core cyclohexenone in cyanobacteria is derived from the shikimate pathway, as has been suggested for eukaryotic organisms. The use of other putative inhibitors did not yield clear evidence, but cerulenin was found to be a potent inhibitor of mycosporine biosynthesis. Using radiolabelled amino acids, we determined the origin of the variable mycosporine amino acidic side chains. We detected specific incorporation of 14 C-glycine and 14 C-serine into the corresponding side chains of mycosporine-glycine and shinorine, demonstrating that free amino acids are their direct precursors. A pulse-chase experiment using 14 C-glycine demonstrated that the monosubstituted mycosporine, mycosporine-glycine, is a direct metabolic precursor of the bisubstituted mycosporine, shinorine. These results support the idea that the large diversity of mycosporine molecules found in nature is produced by variations in late biosynthetic steps, which add amino-moieties to the core. In particular, we can postulate the existence of a shinorine synthase catalysing the condensation of mycosporine-glycine and serine in this cyanobacterium.

A simple and novel route for the synthesis of new terphenyl derivative as well as oxidative aromatization of α,β-unsaturated cyclohexenone to the corresponding phenol derivative is developed. The present work involves the condensation of ethylacetoacetate with 4,4'-difluoro chalcone followed by the aromatization using chloramine-T in acetic acid to yield the title compound (3). The synthesized compound (3) is well characterized by IR, NMR, LCMS and elemental analysis.

We have developed a Pt(COD)Cl(2)-catalyzed hydrative cyclization of 1,6-diynes leading to the formation of functionalized cyclohexenones in good yields.We have developed a Pt(COD)Cl(2)-catalyzed hydrative cyclization of 1,6-diynes leading to the formation of functionalized cyclohexenones in good yields.