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PubMed1987

Effects of anoxia and ischemia on uptake2 of catecholamines in perfused rat heart.

The effects of 30 min periods of either anoxia or ischemia (stop-flow) on the uptake2 of isoprenaline and on the production of O-methyl-isoprenaline, a major metabolite of isoprenaline formed by catechol-O-methyltransferase (COMT), were examined in the perfused rat heart. After either glucose deprivation or anoxia, the uptake2 of isoprenaline in hearts subsequently perfused with isoprenaline and 3',4'-dihydroxy-2-methyl-propiophenone, a COMT inhibitor, was similar to control values. However, uptake2 was decreased following either anoxia in association with glucose deprivation or ischemia. In the absence of the COMT inhibitor, neither glucose deprivation nor anoxia alone had any effect on the production of [3H]3-O-methyl-isoprenaline from [3H]isoprenaline, but both anoxia together with glucose deprivation and stop-flow ischemia decreased it. These findings indicate that both anoxia coupled with glucose deprivation and ischemia inhibit both uptake2 and COMT activity and suggest that such inhibition may be responsible for the high concentration of catecholamines released locally following myocardial infarction.

Animals↗

PubMed1987

Nitrosation products from the plant Ephedra altissima and their potential endogenous formation.

The plant species Ephedra is commonly used in both folk medicine and for the preparation of health teas. Nitrosation of a tea made from Ephedra altissima yielded N-nitrosoephedrine (NEP), N-nitrosopseudoephedrine (NPEP), N-nitrosoproline (NPRO), N-nitrosomethylbenzylamine (NMBA), trace quantities of 2 unidentified non-volatile nitrosamines and the new nitroso compound 2-(N-nitroso-N-methylamino)propiophenone (NMAP). Incubation of a tea extract at 37 degrees C and pH 2.0 under conditions simulating the normal fasting stomach with a constant nitrite concentration (25 microM) for 1 h produced NEP, NPEP, NMAP and NPRO. The synthesis and preliminary results for the mutagenic effect of NMAP on the reversion of Salmonella typhimurium strains TA100 and TA1535 in the Ames test are reported.

Dimethylnitrosamine↗

PubMed1985

Carbonyl reductase activity of sepiapterin reductase from rat erythrocytes.

A homogeneous preparation of sepiapterin reductase, an enzyme involved in the biosynthesis of tetrahydrobiopterin, from rat erythrocytes was found to be responsible for the reduction with NADPH of various carbonyl compounds of non-pteridine derivatives including some vicinal dicarbonyl compounds which were reported in the previous paper (Katoh, S. and Sueoka, T. (1984) Biochem, Biophys. Res. Commun. 118, 859-866) in addition to the general substrate, sepiapterin (2-amino-4-hydroxy-6-lactoyl-7,8-dihydropteridine). The compounds sensitive as substrates of the enzyme were quinones, e.g., p-quinone and menadione; other vicinal dicarbonyls, e.g., methylglyoxal and phenylglyoxal; monoaldehydes, e.g., p-nitrobenzaldehyde; and monoketones, e.g., acetophenone, acetoin, propiophenone and benzylacetone. Rutin, dicoumarol, indomethacin, and ethacrynic acid inhibited the enzyme activity toward either a carbonyl compound of a non-pteridine derivative or sepiapterin as substrate. Sepiapterin reductase is quite similar to general aldo-keto reductases, especially to carbonyl reductase.

Alcohol Oxidoreductases↗

PubMed2004

Synthesis of [O-methyl-11C]1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: a potential PET ligand for CB1 receptors.

Synthesis and in vitro evaluation of [O-methyl-(11)C]1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide ([(11)C]-1), a potential imaging agent for CB(1) receptors using PET is described. 1-(2-Chlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (5), the precursor for radiolabeling, was synthesized from 4-OTBDPS-propiophenone (2) in five steps with 30% overall yield. The reaction of alcohol 5 with [(11)C]MeOTf at 60 degrees C afforded [(11)C]-1 with an average radiochemical yield of 14.5% (EOS) and >2000 Ci/mmol specific activity. The radiotracer was found to selectively label CB(1) receptors in slide-mounted sections of postmortem human brain containing prefrontal cortex as demonstrated by in vitro autoradiography using phosphor imaging.

Autoradiography↗

PubMed2006

Design, synthesis, and biochemical evaluation of novel cruzain inhibitors with potential application in the treatment of Chagas' disease.

A series of compounds bearing tetrahydronaphthalene, benzophenone, propiophenone, and related rigid molecular skeletons functionalized with thiosemicarbazone or unsaturated carbonyl moieties were prepared by chemical synthesis and evaluated for their ability to inhibit the enzyme cruzain. As potential treatment agents for Chagas' disease, three compounds from the group demonstrate potent inhibition of cruzain with IC(50) values of 17, 24, and 80 nM, respectively.

Carbon↗

PubMed2006

The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain.

We developed a reproducible, simple, and small-scale method for determining the re-uptake and release of monoamines (dopamine, serotonin (5-HT) and norepinephrine) using rat brain synaptosomes. These assays were then applied to study the effects of different kinds of non-medically used psychoactive drugs on monoamine re-uptake and release. The phenethylamine derivatives, 4-fluoroamphetamine, 2-methylamino-3,4-methylene-dioxy-propiophenone (methylone), 1-(1,3-benzodioxol-5-yl)-2-butanamine (BDB), and N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB), had strong inhibitory effects on the re-uptake of dopamine, 5-HT and norepinephrine. 4-Fluoroamphetamine, methylone and BDB also strongly increased the release of the three monoamines, but MBDB increased 5-HT and norepinephrine release, but had little effect on dopamine release. However, 2,5-dimethoxy-4-iodophenethylamine (2C-I), 2,5-dimethoxy-4-ethylphenethylamine (2C-E), 2,5-dimethoxy-4-chlorophenethylamine (2C-C), 2,4,5-trimethoxyamphetamine (TMA-2) and 2,4,6-trimethoxyamphetamine (TMA-6), which are methoxylated phenethylamine derivatives, slightly influenced the re-uptake and release of monoamines. Alpha-metyltryptamine (AMT), a tryptamine derivative, was one of the strongest re-uptake inhibitors and releasers of the three monoamines. The tryptamine derivative, 5-methoxy-alpha-methyltryptamine (5-MeO-AMT), also strongly inhibited re-uptake and increased the release of the three monoamines. N,N-dipropyltryptamine (DPT), 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT), 5-methoxy-N,N-methylisopropyltryptamine (5-MeO-MIPT), and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) inhibited monoamine re-uptake, but had a few effects on monoamine release. 1-(3-Chlorophenyl)piperazine (3CPP) and 1-(methoxyphenyl)piperazine (4MPP), which are piperazine derivatives, inhibited monoamine re-uptake and accelerated their release. The results suggest that some designer drugs strongly act on the central nerve system to the same extent as restricted drugs.

Adrenergic Uptake Inhibitors↗

PubMed2006

Beccaridiol, an unusual 28-nortriterpenoid from the leaves of Diplectria beccariana.

A C29-triterpene, beccaridiol (1), a dihydrochalcone natural product, 2',4'-dihydroxy-3-(4-methoxyphenyl)-propiophenone (2), as well as three known compounds, 4'-hydroxy-1',2'-dihydro-beta-ionone, 4'-O-methyldavidigenin (3), and ursolic acid, have been isolated from an EtOAc-soluble extract of the leaves of Diplectria beccariana. Beccaridiol (1) was characterized as an ursane-type 28-nortriterpene possessing an unusual aromatic E-ring by spectroscopic data interpretation. The relative configuration of this unusual isolate was established by analyzing the observed NOESY NMR correlations, and the absolute stereochemistry of 1 was then determined based on the circular dichroism (CD) spectrum of its 2,3-di-p-bromobenzoate (1b) derivative. All isolates were evaluated for their potential cancer chemopreventive properties utilizing a cell culture assay to determine quinone reductase induction.

Enzyme Induction↗

PubMed2000

Anti-leishmanial activity of neolignans from Virola species and synthetic analogues.

Surinamensin, a neolignan isolated from Virola surinamensis, 3,4,5-trimethoxy-8-[2',6'-dimethoxy-4'-(E)-propenylphenoxy]-phenylpropane, a neolignan isolated from Virola pavonis, and 25 of its synthetic analogues or correlated substances with ether linkages and their corresponding C-8 sulphur and nitrogen analogues, were tested for activity against Leishmania donovani amastigotes and promastigotes in vitro. Some were active against L. donovani promastigotes at 30 microM but inactive against intracellular amastigotes. The natural neolignan from V. pavonis was active against promastigotes at 100 microM. The highest selective activity was found in those compounds with sulphur bridges. The beta-ketosulfide (3,4-dimethoxy)-8-(4'-methylthiophenoxy)-propiophenone produced 42% inhibition of L. donovani amastigotes in the liver of BALB/c mice at 100 mg/kg given once daily for five consecutive days (P>0.05).

Animals↗

PubMed2003

Stereoselective biosynthesis of chloroarylpropane diols by the basidiomycete Bjerkandera adusta.

Previously we have shown that 1-arylpropane-1,2-diols are catabolic products of L-phenylalanine during idiophasic metabolism of B. adusta that are stereoselectively biosynthesized from a C(7)-unit (ring+benzylic carbon) and a C(2)-unit as predominantly erythro 1R, 2S enantiomers.In order to probe the mechanism of 1-arylpropane-1,2-diol formation, the products of the incubation of isotopically labelled aromatic aldehydes as substrates with Bjerkandera adusta (DAOM 215869) have been characterized. The aromatic aldehydes were benzaldehyde (ring D(5)) and 4-methoxy- and 4-hydroxybenzaldehydes (ring 13C(6)). These aldehydes were all stereoselectively incorporated into the corresponding 1-arylpropane-1,2-diols, including the chloro analogues, as well as into the corresponding alpha-ketols (phenyl acetyl carbinols (PAC's) and 2-hydroxy propiophenones (2-HPP's)) the presumed precursors of the diols. Benzoic acid (ring D(5)) was likewise incorporated into the diols, chlorodiols and alpha-ketols. These results lead us to conclude that the aromatic aldehydes benzaldehyde, 4-hydroxybenzaldehyde and 4-methoxybenzaldehyde are likely C(7)-unit precursors in the carboligation reaction(s) that leads to 1-arylpropane-1,2-diol biosynthesis. The metabolic role of the diols remains to be elucidated but they may be important intermediates in CAM (chlorinated anisyl metabolite) aldehyde-alcohol cycling and also act as substrates for the chlorination/hydroxylation enzymes yet to be identified in white rot fungi.

Acetylation↗

PubMed2002

Quantitative and structural determination of pseudoephedrine sulfate and its related compounds in pharmaceutical preparations using high-performance liquid chromatography.

A simple isocratic reversed-phase high performance liquid chromatograghic method for the separation of pseudoephedrine and its related compounds in pharmaceutical formulations is described. The separation is achieved in less than 35 min on a C-18 column (4.6 mm I.D. x 25 cm length, 5-micrometer particle size) using a mobile phase consisting of a mixture of ammonium acetate and methanol. The results described in this report demonstrate that the method is sensitive and selective. Structural elucidation of two new pseudoephedrine degradation products is described. On the basis of structural analysis by liquid chromatography-mass spectrometry (LC-MS) and liquid chromatography-nuclear magnetic resonance spectroscopy (LC-NMR), the two newly elucidated degradation products were identified to be 2-(carboxyamino)propiophenone (molecular ion of m/z=194) and 2-formyl-2-(methylamino)-acetophenone (molecular ion of m/z=178).

Chromatography, High Pressure Liquid↗

PubMed2005

Interactions of Rh(III)-dihydrido-bis(phosphine) complexes with semicarbazones.

Interaction of cis,trans,cis-[Rh(H)2(PR3)2(acetone)2]PF6 complexes (R = aryl or R3 = Ph2Me, Ph2Et) under H2 with E-semicarbazones gives the Rh(III)-dihydrido-bis(phosphine)-semicarbazone species cis,trans-[Rh(H)2(PR3)2{R'(R' ')C=N-N(H)CONH2}]PF6, where R' and R' ' are Ph, Et, or Me. The complexes are generally characterized by elemental analysis, 31P{1H} NMR, 1H NMR, and IR spectroscopies, and MS. X-ray analysis of three PPh3 complexes reveals chelation of E-semicarbazones by the imine-N atom and the carbonyl-O atom. In contrast, the corresponding reaction of [Rh(H)2(PPhMe2)2(acetone)2]PF6 with acetophenone semicarbazone gives the ortho-metalated-semicarbazone species cis-[RhH(PPhMe2)2{o-C6H4(Me)C=N-N(H)CONH2}]PF6. The X-ray structure of E-propiophenone semicarbazone is also reported. Rhodium-catalyzed, homogeneous hydrogenation of semicarbazones was not observed even at 40 atm H2.

Journal Article↗

PubMed2005

Stereoselective enolizations mediated by magnesium and calcium bisamides: contrasting aggregation behavior in solution and in the solid state.

The reactions of magnesium and calcium bis(hexamethyldisilazide) with propiophenone have been studied with a view to determine the utility of these bases in the stereoselective enolization of ketones and to uncover the nature of the metal enolate intermediates produced. Both base systems are highly Z-selective when the reactions are conducted in the presence of polar solvents. However, in situ monitoring of the magnesium system in arene solution revealed a preference for E-enolate formation, which was confirmed by silyl enol ether trapping studies. Solution NMR studies of the magnesium system in toluene-d8 show the presence of a monomer-dimer equilibrium for the intermediate amidomagnesium enolates. This assignment is supported by the characterization of a disolvated amidomagnesium enolate dimer by crystallographic analysis. Comparative studies of the calcium system show distinctly different behavior. This is exemplified by the characterization of a novel solvent-separated ion pair complex and a monomeric amidocalcium enolate in the solid state. Solution NMR studies of the calcium system in pyridine-d5 reveal the co-existence of the heteroleptic amidocalcium enolate, the bisamide, the bisenolate and the ion pair complex.

Journal Article↗

PubMed2006

Kinetics and mechanism of ketone enolization mediated by magnesium bis(hexamethyldisilazide).

Magnesium bis(hexamethyldisilazide), Mg(HMDS)(2), reacts with substoichiometric amounts of propiophenone in toluene solution at ambient temperature to form a 74:26 mixture of the enolates (E)- and (Z)-[(HMDS)(2)Mg(2)(mu-HMDS){mu-OC(Ph)=CHCH(3)}], (E)-1 and (Z)-1, which contain a pair of three-coordinate metal centers bridged by an amide and an enolate group. The compositions of (E)-1 and (Z)-1 were confirmed by solution NMR studies and also by crystallographic characterization in the solid state. Rate studies using UV-vis spectroscopy reveal the rapid and complete formation of a reaction intermediate, 2, between the ketone and magnesium, which undergoes first-order decay with rate constants independent of the concentration of excess Mg(HMDS)(2) (DeltaH++ = 17.2 +/- 0.8 kcal/mol, DeltaS++ = -11 +/- 3 cal/mol.K). The intermediate 2 has been characterized by low-temperature (1)H NMR, diffusion-ordered NMR, and IR spectroscopy and investigated by computational studies, all of which are consistent with the formulation of 2 as a three-coordinate monomer, (HMDS)(2)Mg{eta(1)-O=C(Ph)CH(2)CH(3)}. Further support for this structure is provided by the synthesis and structural characterization of two model ketone complexes, (HMDS)(2)Mg(eta(1)-O=C(t)Bu(2)) (3) and (HMDS)(2)Mg{eta(1)-O=C((t)Bu)Ph} (4). A large primary deuterium isotope effect (k(H)/k(D) = 18.9 at 295 K) indicates that proton transfer is the rate-limiting step of the reaction. The isotope effect displays a strong temperature dependence, indicative of tunneling. In combination, these data support the mechanism of enolization proceeding through the single intermediate 2 via intramolecular proton transfer from the alpha carbon of the bound ketone to the nitrogen of a bound hexamethyldisilazide.

Journal Article↗

PubMed1977

New inhibitors of steroid 11beta-hydroxylase. Structure--activity relationship studies of metyrapone-like compounds.

A series of metyrapone analogues was synthesized for study as inhibitors of steroid 11beta-hydroxylase. Racemic mixtures of the new compounds were evaluated in vitro. Preliminary results revealed several analogues to be effective inhibitors of deoxycorticosterone hydroxylation. 2-(3-pyridyl)propiophenone (13) and alpha,beta-diphenyl-3-pyridineethanol (16) were the most active new compounds. Each was 65% as potent as metyrapone; 3-Pyridyl alpha-3-pyridylbenzyl ketone (3), 2-phenyl-2-(3-pyridyl)acetophenone (4), alpha-(diphenylmethyl)-3-pyridinemethanol (17), and 1,2-di-3-pyridyl-1-propanol (26) were 52, 32, 25, and 41% as inhibitory as metyrapone, respectively. Diphenylmethyl 3-pyridyl ketone (5), benzyl 3-pyridyl ketone (10), 2-(3-pyridyl)acetophenone (12), 2-phenyl-1-(3-pyridyl)-1-propanone (11), alpha,beta-di-3-pyridylphenethyl alcohol (15), and 1,2-di-3-pyridylethanol (27) had less than 25% the activity of metyrapone. All compounds displaying a metyrapone-like inhibition contained appropriately substituted alcoholic or ketonic functions. A phenyl or methyl group alpha to the carbon bearing the oxygen was necessary for appreciable activity. A 3-phridyl group alpha to the carbonyl carbon could be replaced by a phenyl group. For optimal activity, however, the other 3-pyridyl group of metyrapone could not be exchanged for a phenyl group.

Adrenal Cortex↗

PubMed1976

Adamantanamine derivatives. Antimicrobial activities of certain Mannich bases.

A series of Mannich condensation products containing the beta-(1-adamantylamino)propiophenone skeleton (type I) and the o-(1-adamantylaminomethyl)phenol skeleton (type II) was synthesized and tested for antimicrobial activity against certain bacteria and fungi by the agar diffusion and tube dilution methods. Type I compounds were more active than type II compounds and had a broad-spectrum effect on certain gram-negative and gram-positive bacteria, acid-fast bacteria, a yeast, and a mold.

Amantadine↗

PubMed1983

Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 1. Synthesis and estrogen receptor binding affinity of 2,2'- and 3,3'-disubstituted hexestrols.

The syntheses of symmetrically 3,3'- and 2,2'-disubstituted meso hexestrol derivatives are described [3,3'-substituents: OH (1), F (2), Cl (3), Br (4), I (5), CH2N(CH3)2 (6), CH3 (7), CH2OCH3 (8), CH2OC2H5 (9), CH2OH (10), NO2 (11), NH2 (12), N(CH3)2 (13), COCH3 (14), and C2H5 (15); 2,2'-substituents: OH (16), F (17), Cl (18), Br (19), CH3 (20), and C2H5 (21)]. The synthesis of 1-3 was accomplished by reductive coupling of the propiophenones with TiCl4/Zn and subsequent hydrogenation of the cis-3,4-diphenylhex-3-enes. Compounds 4-15 were obtained by substitution of hexestrol, while compounds 16-21 were synthesized by coupling the 1-phenyl-1-propanols with TiCl3/LiAlH4 and separation of the meso diastereomers. The binding affinity of these compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. All test compounds showed relative binding affinity (RBA) values between 32 and less than 0.01% that of estradiol. Only meso-3,4-bis(2,4-dihydroxyphenyl)hexane (16) showed an estrogen receptor binding affinity comparable to that of hexestrol (32 and 27%, respectively). Compounds exhibiting RBA values of greater than 5% were evaluated in the mouse uterine weight test. All of them showed uterotrophic activity. Compounds 2, 7, 16, 17, and 20 were strongly active in very small doses (1 microgram per animal per day), while 1 and 12 produced full uterotrophic effects only in high doses and inhibited the estrone-stimulated uterine growth strongly in small doses (59 and 78% inhibition, respectively).

Animals↗

PubMed1984

Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 2. Synthesis and estrogen receptor binding affinity of 4,4'-, 5,5'-, and 6,6'-disubstituted metahexestrols.

The syntheses of symmetrically 4,4'-, 5,5'-, and 6,6'-disubstituted derivatives of the mammary tumor inhibiting antiestrogen metahexestrol [meso-3,4-bis(3-hydroxyphenyl)hexane] (1) are described [4,4'-substituents: F, (2), Cl (3), Br (4), I (5), CH2N (CH3)2 (6), CH3 (7), CH2OCH3 (8), CH2OC2H5 (9), CH2OH (10), NO2 (11), NH2 (12), N(CH3)2 (13), COCH3 (14), and C2H5 (15); 5,5'-substituents: OH (16) and Cl (17); 6,6'-substituents: OH (18), F (19), Cl (20), and CH3 (21)]. The synthesis of 1-3, 16, and 19 was accomplished by reductive coupling of the propiophenones with TiCl4 /Zn and subsequent hydrogenation of the cis-3,4- diphenylhex -3- enes . Compounds 17, 18, 20, and 21 were synthesized by coupling the 1-phenyl-1-propanols with TiCl3 /LiAlH4 and separation of the meso diastereomers, while 4-15 were obtained by substitution of metahexestrol . The binding affinity of these compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. The test compounds showed relative binding affinity (RBA) values between 15 and less than 0.01% that of estradiol. Only compound 21 showed an estrogen receptor binding affinity exceeding that of metahexestrol (15 and 10%, respectively). Compounds exhibiting RBA values of greater than 0.5% were evaluated in the mouse uterine weight test. They showed a similar (2 and 12), slightly increased (19 and 21), or strongly enhanced (7 and 20) estrogenicity compared to that of metahexestrol . Compounds 1, 2, 7, 12, and 21 exhibited antiestrogenic activity inhibiting the estrone-stimulated uterine growth (24 to 60% inhibition).

Aging↗

PubMed2004

Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones.

The influence of electronic effects on the enantioselectivity of the oxazaborolidine-catalyzed asymmetric borane reduction of ketones has been observed and investigated with use of para-substituted acetophenones and propiophenones with a variety of functional groups and B-unsubstituted and B-methoxyoxazaborolidines derived from (S)-2-(diphenylhydroxymethyl)pyrrolidine with borane and trimethyl borate as catalysts in toluene and THF. The results indicate that Hammett linear free energy electronic effects on the enantioselectivity in the asymmetric reduction were observed and rationalized. Tuning electronic effects of the catalyst can improve the enantioselectivity in the reduction. Another interesting finding to be noted is that anions heavily affect the enantioselectivity, especially for the B-methoxy catalyst, because of their coordination with the boron atom in the catalysts.

Journal Article↗