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PubMed2000

Suppression of furylfuramide-induced SOS response by acetophenones using Salmonella typhimurium TA1535/pSK1002 umu test.

The recently isolated paeonol (2-hydroxy-4-methoxyacetophenone), as one of the antimutagenic compounds from Discorea japonica, was used as a lead compound for detailed structure-activity relationship studies. Nine acetophenones (2-hydroxy-4-methoxy, 2-hydroxy-5-methoxy, 2-hydroxy-6-methoxy, 4-hydroxy-3-methoxy, o-methoxy, m-methoxy, p-methoxy, and 2,5-dimethoxyacetophenone and acetophenone) were investigated for their ability of suppression of furylfuramide-induced SOS response using Salmonella typhimurium TA1535/pSK1002 in the umu test, against the mutagen, 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide). The results showed that 2-hydroxy-6-methoxyacetophenone displayed the strongest activity (EC(50) = 0.6 micromol/mL), and a hydroxyl group at C-2 is necessary feature for acetophenone derivatives to show the suppressive effects of furylfuramide-induced SOS response.

Acetophenones↗
PubMed1987

Leukotriene receptor antagonists. 2. The [[(tetrazol-5-ylaryl)oxy]methyl]acetophenone derivatives.

A series of [[(tetrazol-5-ylaryl)oxy]methyl]acetophenones was synthesized and evaluated as antagonists of leukotriene D4 induced contractions of guinea pig ileum. Substitutions at the 3-position of the acetophenone with ethyl (66), propyl (68), butyl (83), and isobutyl (84) gave -log IC50 values of 7.9, 8.0, 7.8, and 7.7, respectively. Equally potent compounds were obtained when the tetrazol-5-yl group was connected to the second benzene ring in the para position with a chemical bond (67), methylene (68), or ethylene (71). For retention of high antagonist activity, the acetophenone should be substituted in the 2-position by a hydroxyl group and the tetrazole ring should have an acidic hydrogen atom. 1-[2-Hydroxy-3-propyl-4-[[4-(1H-tetrazol-5-ylmethy) phenoxy]methyl]phenyl]ethanone (68, LY1632443) has undergone extensive pharmacologic evaluation for its potential as an antiasthma agent.

Acetophenones↗
PubMed1987

Hypolipidemic activity of o-(N-phthalimido)acetophenone in Sprague Dawley rats.

o-(N-Phthalimido)acetophenone has proven to be an effective hypolipidemic agent in rats at 20 mg/kg/day orally. The agent suppressed the activity of the rate-limiting enzyme of the liver involved in de novo synthesis of triglycerides. The synthetic rate-limiting enzyme for cholesterol esters was also inhibited by the drug in vivo. o-(N-Phthalimido)acetophenone lowered cholesterol in the liver and the aorta wall and generally caused an increase in phospholipids in body tissues. Serum lipoproteins were modulated by the drug with a decrease in cholesterol and triglycerides in the chylomicron, very low-density lipoproteins (VLDL), and low-density lipoproteins (LDL) and an increase in high-density lipoprotein (HDL) cholesterol. The phospholipid content was increased in the chylomicron, VLDL, and LDL fractions. In hyperlipidemic rats, o-(N-phthalimido)acetophenone lowered elevated blood lipid levels at 20 mg/kg/day orally after 3 weeks of administration. The hypolipidemic rat after drug treatment had a lower LDL cholesterol and a higher HDL cholesterol content, which is therapeutically desirable to protect against cardiovascular disease.

Acetophenones↗
PubMed2001

Antifungal activity of some mono, bis and quaternary Mannich bases derived from acetophenone.

The development of resistance to current antifungal therapeutics drives search for new effective agents. Some Mannich bases have antifungal activity, but no information is available regarding the antifungal activity of acetophenone derived Mannich bases. Mono Mannich bases of acetophenone 1-3 were synthesized and converted into their corresponding bis derivatives, 5-7. Representative quaternary derivatives 4 and 8 were also synthesized. Antifungal activities of the compounds were evaluated using some yeasts and dermatophytes in vitro. Mono Mannich base 3 and quaternary compounds 4 and 8 were found to be 2-16 times more potent than the reference compound amphotericin B against dermatophytes: Trichophyton rubrum, Trichophyton mentagrophytes, and Microsporum canis. Compounds 4 and 8 were also found to be 2 times more effective compared with amphotericin B against the yeast Saccharomyces cerevisiae. Quaternization procedure improved the biological activity dramatically, whereas conversion of mono Mannich bases to corresponding bis derivatives generally did not affect antifungal activity. Our results suggest that acetophenone derived mono Mannich base 3 and quaternary derivatives 4 and 8 may serve as leading compounds for further studies to develop new antifungal agents with their highly potent antifungal activity.

Acetophenones↗
PubMed1999

Plant-derived acetophenones with antiasthmatic and anti-inflammatory properties: inhibitory effects on chemotaxis, right angle light scatter and actin polymerization of polymorphonuclear granulocytes.

3-Methoxy- and 2-hydroxy-3-methyl substituted 4-hydroxyacetophenones and some of the corresponding 4-O-glucosides revealed inhibitory activity on LTB4-, fMLP- and PAF-induced chemotaxis of polymorphonuclear granulocytes (PMN). Blocking of PMN myeloperoxidase (MPO), which is required for the intracellular activation of acetophenones, caused a loss of activity. By in vitro activation of apocynin (1) with human MPO and H2O2 and subsequent chromatographic purification an apocynin-free fraction was obtained, which contained the major metabolite. The fraction showed strong anti-chemotactic activity, which was largely preserved despite of MPO-blockade. The influences on right angle light scatter and actin polymerization in PMN demonstrate the inhibitory effects of acetophenones on the cytoskeletal rearrangement after stimulation with fMLP. Acetosyringenin (2) was shown to reduce mastoparan-induced PMN migration. The inhibition of receptor independent motility of PMN suggests that the active metabolites of acetophenones may interfere with the post receptor signalling.

Acetophenones↗
PubMed2000

alpha,alpha-gem-Difluorination of alpha-(alkylthio)acetophenone derivatives with N-fluoropyridinium salts.

The alpha,alpha-gem-difluorination of 2',4'-difluoro-alpha-(methylthio)acetophenone (1a) with N-fluoropyridinium salts gave 2',4',alpha,alpha-tetrafluoro-alpha-(methylthio)acetophenone (3a). This reaction was accelerated by the addition of zinc chloride, zinc bromide or anhydrous iron(III) chloride, and higher yields than the reaction without additives were obtained. The gem-difluorination reaction using FP-T300 in the presence of zinc bromide was applicable to other alpha-(alkylthio)acetophenone derivatives (1).

Acetophenones↗
PubMedDate not supplied

The disposition of the hypolipidemic agent, o-(N-phthalimido)acetophenone, in Sprague-Dawley rats.

Disposition studies of the potent experimental hypolipidemic agent, o-(N-phthalimido)acetophenone, were conducted in the laboratory rat. Intravenous administration of the drug demonstrated a declining biphasic plasma concentration-time curve suggesting a rapid distribution into tissues. Less than 5% of the intravenous dose was recovered in urine and feces after 5 days. Oral administration of the drug showed that the maximum blood levels were attained within 15 min. After 48 hr, 92% of the orally administered 14C dose was eliminated either via urine (60%) or feces (40%). 14C in a 0-24-hr urine collection after oral administration showed that urinary radioactivity was composed of 22% of the parent compound o-(N-phthalimido) acetophenone, a benzoic acid metabolite (22%) o-(N-phthalimido)benzoic acid, and an amic acid metabolite (56%) N-(o-acetophenone)phthalamic acid. The two metabolites were unconjugated and possessed less hypolipidemic activity than the parent drug.

Acetophenones↗
PubMed1982

Attenuation of the development of hypertension in spontaneously hypertensive rats by the thromboxane synthetase inhibitor, 4'-(imidazol-1-yl) acetophenone.

The compound 4'-(imidazol-1-yl) acetophenone was demonstrated to be a selective thromboxane (Tx) synthetase inhibitor in spontaneously hypertensive rats (SHR). Serum TxB2 concentrations (from clotted blood) were suppressed by 89.1% (p less than 0.001) and 41.2% (p less than 0.01) at 3 and 24 hours, respectively, following a single subcutaneous injection of 100 mg/kg of 4'-(Imidazol-1-yl) acetophenone suspended in olive oil. In contrast, plasma 6-keto-PGF1 alpha levels were not significantly altered at 3 hours following injection - a time when suppression of TXB2 was maximal. From 4 to 10 weeks of age, SHR were treated with daily injections of either 4'-(Imidazol-1-yl) acetophenone (100 mg/kg) in olive oil or olive oil alone. By 8 weeks of age systolic blood pressures in the treated group were 140.6 +/- 3.2 vs 156.6 +/- 4.5 mmHg in the control group (p less than 0.01). At ten weeks of age the separation was even more pronounced: 155.3 +/- 3.7 vs. 184.8 +/- 4.6 mmHg for treated vs. control animals (p less than 0.001). This data supports the hypothesis that thromboxanes may be involved in the development of SHR hypertension; however, alternative mechanisms are discussed.

6-Ketoprostaglandin F1 alpha↗
PubMed2002

Correlations of chemical mass shifts of para-substituted acetophenones and benzophenones with Brown's sigma constants.

Relationships between chemical mass shifts and physiochemical properties of ions are sought by examining substituted acetophenones, benzophenones, and pyridines in a modified ion trap mass spectrometer. Systematic changes in chemical mass shift occur with changes in substituent in the acetophenones and the benzophenones. Brown's sigma+ constant, which is a measure of electronic effects of substituents in reactions that involve positive charge development, is shown to correlate linearly with chemical mass shifts in para-substituted acetophenones and benzophenones. Brown's sigma+ constant also correlates with the ease of dissociation of the ions via a correlation with ionization energy. It is suggested that ease of dissociation is the underlying factor in determining chemical mass shifts. The experimental results also suggest that dissociative collisions between ions and buffer gas make a much greater contribution to chemical mass shifts than do elastic collisions.

Journal Article↗
PubMed2003

Quantum mechanical study of stereoselectivity in the oxazaborolidine-catalyzed reduction of acetophenone.

Chiral oxazaborolidines, known as CBS catalysts after the work of Corey, Bakshi and Shibata, are used for the stereoselective reduction of prochiral ketones to secondary chiral alcohols. Due to their relative low cost, ease of use, and high selectivity, their popularity has remarkably grown in the last 15 years. Oxazaborolidine-catalyzed reductions have been much studied, both experimentally and computationally, by means of semiempirical methods. Though, a more accurate high level quantum mechanical study on the complete system, capable of elucidating reliably the origins of stereoselectivity, is still lacking. Therefore, the acetophenone (PhMK) reduction with Corey's oxazaborolidine has been modeled for the first time with ab initio and DFT-B3LYP calculations on the complete system as well as with AM1. Calculations on the complexation of BH(3) to CBS, which can occur only in a cis fashion with respect to the hydrogen on the stereogenic C-4 carbon atom, have allowed us to confirm the great rigidity of Corey's catalyst, possibly determining its excellent enantioselectivity. Acetophenone-CBS-BH(3) complexes were characterized at various levels of theory, and it was found that the picture obtained depends heavily on the method adopted. A computational strategy for identifying the hydride transfer transition states of the competing pathways was developed and tested, using a model system for which the transition state geometry was already known. The application of the TS search method to the reduction of acetophenone allowed the characterization of the TS's for the competing pathways in this reaction, making it possible to predict with good quantitative accuracy the stereochemical outcome of the reaction at all the levels of theory adopted. The characterization of the intermediate oxazadiboretane products confirmed that the highly exothermic hydride transfer provides the thermodynamical drive for the reaction.

Journal Article↗
PubMed1989

Induction of peroxisomal beta-oxidation in the rat liver in vivo and in vitro by tetrazole-substituted acetophenones: structure-activity relationships.

LY171883, a leukotriene D4 antagonist in the tetrazole-substituted acetophenone structural class, previously was demonstrated to cause peroxisome proliferation in rodents. In the present studies, several analogs were tested to determine if there are structural requirements for the induction of peroxisomal beta-oxidation in the rat liver in vivo and in cultured rat hepatocytes. Liver weight and serum triglycerides also were measured in vivo. The increases in peroxisomal beta-oxidation caused by the tetrazole-substituted acetophenones in vivo ranged from negligible to greater than 17-fold and there was good agreement with the structure-activity relationships found in cultured hepatocytes. N-methylation of the acidic nitrogen of the tetrazole blocked the peroxisomal effects, indicating that the free acid was required for activity. The length of the alkyl chain linked to the tetrazole also influenced the activity of the compounds. However, the more important determinant of peroxisomal activity may be the spatial orientation of the acidic tetrazole with respect to the planar backbone of the molecule. The data indicate there is a target site for peroxisome proliferation in the liver that is able to distinguish between structurally similar analogs. This site appears to be distinct from the leukotriene receptor since both inducers and noninducers of peroxisomal beta-oxidation were shown previously to be potent leukotriene antagonists.

Acetophenones↗
PubMed2000

Choleretic activity of phloracetophenone in rats: structure-function studies using acetophenone analogues.

The relationship between the chemical structure and choleretic activity of phloracetophenone (2,4,6-trihydroxyacetophenone) was investigated in adult male rats. Fourteen acetophenone analogues, with different substituents on the benzene nucleus, were intraduodenally administered and bile samples were collected via a bile fistula. All of the compounds tested immediately induced choleresis. For the same number of substituents on the benzene ring, hydroxy analogues induced a greater choleresis. The number and position of hydroxy substituents on the benzene nucleus play an important role in determining choleretic activity and biliary secretion of bile acid, but had no relation to biliary excretion of cholesterol. The choleretic activity of the hydroxylated compounds was inversely related to hydrophobicity, as inferred by thin-layer chromatography (TLC). Among the hydroxylated acetophenone analogues, 2,4,6-trihydroxyacetophenone was identified as the most potent, with a choleretic activity of 231.8+/-6.1 microl/mmol/min. It induced both a high bile flow rate and a high bile salt output and led to lower plasma cholesterol levels. This bile had a low lithogenic potential. The results suggest that a structural requirement for high choleretic activity of 2,4,6-trihydroxyacetophenone is a substituent hydroxy group at 4-position. Additional hydroxy groups at 2- and 6-positions are essential for the induction of higher an output of bile acid, and possibly, other solid materials.

Acetophenones↗
PubMed2000

Cytotoxic activities of mono and bis Mannich bases derived from acetophenone against Renca and Jurkat cells.

Mannich bases of acetophenones have been disclosed to have antitumour and cytotoxic activities. 1-Phenyl-3-dimethylaminopropan-1-one hydrochloride, 1, and related piperidino, 2, and morpholino, 3, derivatives, and compound 4, which is a quaternary form of 1, were synthesized as mono Mannich bases derived from acetophenone. They were converted to corresponding bis Mannich bases, 5-8, to see whether it increases the bioactivity. The biological activity of the compounds was examined by cytotoxicity against mouse renal carcinoma (Renca) and transformed human T-lymphocyte (Jurkat) cell lines. Conversion of mono Mannich bases to corresponding bis Mannich bases remarkably increased the cytotoxicity in most cases. Quaternization procedure also improved the bioactivity in mono derivatives against Jurkat cells. Bis mannich bases 5-7 were found to be more active than 5-fluorouracil (6-23 fold) and melphalan (1.25-5 fold) against Renca cells. Except 2 and 8, the compounds synthesised were found to be more active than 5-fluorouracil (1.2-33 fold) against Jurkat cells.

Acetophenones↗
PubMed1988

Inhibition of hepatic fatty acid oxidation at carnitine palmitoyltransferase I by the peroxisome proliferator 2-hydroxy-3-propyl-4-[6-(tetrazol-5-yl) hexyloxy]acetophenone.

Recent studies suggest that the induction of peroxisomal beta-oxidation in rodents may represent an adaptive response to disturbances in hepatic lipid metabolism. The following studies were done to determine the effects of 2-hydroxy-3-propyl-4-[6-(tetrazol-5-yl)hexyloxy]acetophenone (4-THA), a tetrazole-substituted acetophenone which induces peroxisomal beta-oxidation in rodent liver, on fatty acid oxidation in vitro. In isolated hepatocytes, 4-THA inhibited the oxidation of oleate (C18:1) and decreased the mitochondrial redox state. The inhibition was more pronounced in the presence of 0.2 mM-oleate than with 0.5 mM, indicating the inhibition may be competitive. 4-THA had no effect on the oxidation of octanoate (C8:0), suggesting that the site of inhibition of oleate oxidation was the carnitine-dependent transport across the mitochondrial inner membrane. In rat liver mitochondria, 4-THA inhibited carnitine palmitoyltransferase I (CPT-I) competitively with respect to the substrate palmitoyl-CoA, increasing the apparent Km from 19 microM to 86 microM. The inhibition of CPT-I by 4-THA was independent of the concentration of the co-substrate carnitine. Whereas fasting attenuated the inhibition of CPT-I by malonyl-CoA, it did not diminish the inhibition by 4-THA. Inhibition of transferase activity by 4-THA and malonyl-CoA was attenuated in mitochondria which had been solubilized with octyl glucoside to expose the latent form of carnitine palmitoyltransferase (CPT-II), suggesting that the inhibition was specific for CPT-I. The specificity was further demonstrated in studies of mitochondrial beta-oxidation in which 4-THA inhibited the oxidation of palmitoyl-CoA but not palmitoylcarnitine. The results demonstrate that 4-THA inhibits fatty acid oxidation in rat liver in vitro at the site of transport across the mitochondrial inner membrane, CPT-I. Whether this disruption in mitochondrial oxidation is causally related to the induction of peroxisomal beta-oxidation is yet to be determined.

Acetophenones↗
PubMed1999

Aggregation inhibitory activity of minor acetophenones from Paeonia species.

Two minor acetophenones, 2,5-dihydroxy-4-methoxy-acetophenone (2) and 2,5-dihydroxy-4-methylacetophenone (7) from Paeonia species were found to selectively inhibit the aggregation of rabbit platelets induced by arachidonic acid. They were more potent than the major compound, paeonol (1), and 7 also inhibited the formation of TXA2 and PGD2 from arachidonic acid.

Acetophenones↗
PubMed2005

Acetophenone derivatives and sesquiterpene from Euphorbia ebracteolata.

Two new acetophenone derivatives and a new sesquiterpene, along with four known acetophenone compounds, were isolated from the roots of Euphorbia ebracteolata. The structures of the new compounds were identified as 2,2',4,4'-tetrahydroxy-6,6'-dimethoxy-3,3'-dimethyl-7,5'-bisacetophenone, 2,4-dihydroxy-6-methoxy-3-methylacetophenone 4-O-alpha-L-arabinofuranosyl-(1-->6)-beta- D-glucopyranoside and decahydro-1a,4a,7,7-tetramethyl-1H-cycloprop[e]azulene-2,5-diol (1a R,2 R,4a S,5 S,7a R,7b R) using 1D and 2D NMR spectroscopy and X-ray crystallography.

Acetophenones↗
PubMed1998

Anti-inflammatory activity of acetophenones from Ophryosporus axilliflorus.

Seven acetophenone derivatives were isolated from the aerial parts of Ophryosporus axilliflorus (Griseb.) Hieron. These compounds were subjected to the carrageenan-induced mouse paw edema test where tremetone (7) showed extremely anti-inflammatory activity. Furthermore, the non-benzofuran acetophenones 5 and 6, showed a significant response.

Acetophenones↗
PubMed1980

Effect of sample pretreatment on sorption of acetophenone by soils and sediments.

The effect of several sample pretreatment storage techniques, the effect of degree of grinding, and the effect or organic matter removal on the sorption of acetophenone was examined. No significant difference in the sorption of acetopheonone was observed when air-dried, freeze-dried, oven-dried, frozen, or samples kept at 2 degrees C (fresh) were compared. All pretreatment storage techniques resulted in linear sorption isotherms and gave good fits to the modified Freundlich equation (Cs = Kp . Cw). No significant differences in sorption constants (Kp) were observed for samples with a 2 mm maximum diameter when compared to samples ground to 0.6 mm maximum diameter or 0.25 mm maximum diameter. Organic matter removal resulted in decreased Kp values for samples containing more than 1% organic carbon initially but increased Kp values for samples containing less than 1% organic carbon before removal. Expandable 2:1 clay mineral content was significantly correlated with adsorption of acetophenone after organic matter removal.

Acetophenones↗