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PubMed1999

Enatioseparation and anti-rhinovirus activity of 3-benzylchroman-4-ones.

In a series of homo-isoflavonoids, chloro-substituted rac-3-benzylchroman-4-ones (3 d-f) showed an antiviral in vitro activity against selected picornaviruses. In order to study the anti-rhinovirus activity of each stereoisomer, racemic mixtures of 3 d and 3 e were successfully resolved by high-performance liquid chromatography, using a Whelk-O 1 column as chiral stationary phase. The CD spectra confirm that the two eluates of each compound are enantiomers but do not allow the assignment of their absolute configurations. The antiviral activity of the isomers and their racemates was tested in vitro against human rhinovirus serotype 1B and 14 infection, by means of the plaque reduction assay. All homoisoflavonoids tested exhibited an inhibitory effect on rhinovirus replication with an activity depending on virus serotype and compound. The two enantiomers of each compound and the corresponding racemate were equipotent, clearly showing that the configuration of the chiral center in position 3 does not influence the activity against both rhinovirus serotypes.

Antiviral Agents↗
PubMed1988

Mass spectrometry of electrophore-labeled nucleosides. Pentafluorobenzyl and cinnamoyl derivatives.

Three structurally similar deoxynucleosides (thymidine, O4-ethylthymidine, and 2'-deoxyuridine) were studied by mass spectrometry as pentafluorobenzyl, cinnamyl, or mixed derivatives. The purpose of the work was to define the usefulness of such derivatives for structural elucidation of deoxynucleosides. The compounds were ionized in three ways: electron capture negative ion, positive ion chemical ionization, and electron impact. For each of the derivatives examined, the combined spectra were well suited for structural elucidation purposes.

Benzyl Compounds↗
PubMed2004

Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol.

The newly emerged adults of Parasarcophaga dux were treated topically with various doses of myristicin and apiol isolated from roots of dill plant, Anethum graveolus. The compounds toxicity and the dehydrogenase activities of the treated stage and its subsequent developmental stages were studied. The results indicated that apiol more toxic than myristicin. The spectrophotometric evaluation exhibited changes in dehydrogenase activities after treatments. Compounds increased the activities of both alpha-GPDH and MDH in first half of metamorphosis (immature stages). But, the level of ME activities of the various stages was obviously decreased.

Allylbenzene Derivatives↗
PubMed1975

Biosynthesis of bacterial menaquinones. Menaquinone mutants of Escherichia coli.

The isolation of six menaquinone mutants of Escherichia coli is described. It was shown that the mutants fall into two genetic classes. The first class carries mutations in a gene designated menA, which was located at minute 78 on the E. coli chromosome by cotransduction with the glpK and metB genes. The second class carries mutations in a gene designated menB. It was shown that this gene was not cotransducible with the menA gene. The biosynthesis of menaquinone in E. coli was studied using a variety of mutants blocked in aromatic biosynthesis together with the two classes of menaquinone mutants. It was demonstrated that chorismate is the branch point compound leading to menaquinone, and that 2-succinylbenzoic acid and 1,4-dihydroxy-2-naphthoic acid can serve as menaquinoone precursors in E. coli. It was also shown that menA- and menB- strains accumulate 1,4-dihydroxy-2-naphthoic acid and 2-succinylbenzoic acid, respectively, in their culture supernatants. The accumulation of the two compounds by the mutants together with their activity as menaquinone precursors provide strong evidence that they ar true intermediates in menaquinone biosynthesis. A pathway is proposed for the biosynthesis of bacterial menaquinones in which each intermediate has been adequately characterized.

Benzyl Compounds↗
PubMed1980

[New cerebrally active basic dithienyl compounds (author's tranls)].

A review on new cerebrally active basic dithienyl compounds related to (+)-(R)-alpha-((S)-1-[(3,3-di-3-thienylallyl)amino]-ethyl)-benzylalcohol (tinofedrine) is presented. Tinofedrine was selected out of a large number of related compounds on account of its high increase of cerebral blood flow, its improvement of heart performance, of the metabolism of the brain, and because it is well toleraded. Different routes of synthesis are discussed.

Animals↗
PubMed1991

Synthesis and antiarrhythmic activity of cis-2,6-dimethyl-alpha,alpha-diaryl-1-piperidinebutanols.

A series of alpha,alpha-diaryl-1-piperidinebutanols was evaluated for antiarrhythmic activity in the coronary ligated dog model. Structure-activity relationship studies indicated that the 2,6-dimethylpiperidine group yielded compounds with the best antiarrhythmic profiles in this series. The length of the methylene chain separating the diarylcarbinol and the amino group was not crucial. Substitution of a hydrogen or a number of functional groups for the hydroxyl group had little effect on efficacy or duration but yielded compounds that produced severe tachycardias. Replacement of one of the aryl groups by hydrogen or a pyridinyl or cyclohexyl group had little effect on efficacy but decreased the duration of action. Compound 18 (pirmenol) was ultimately chosen for further studies and is now being investigated in man.

Animals↗
PubMed2006

Acyl-based anandamide uptake inhibitors cause rapid toxicity to C6 glioma cells at pharmacologically relevant concentrations.

Compounds blocking the uptake of the endogenous cannabinoid anandamide (AEA) have been used to explore the functions of the endogenous cannabinoid system in the CNS both in vivo and in vitro. In this study, the effects of four commonly used acyl-based uptake inhibitors [N-(4-hydroxyphenyl)arachidonylamide (AM404), N-(4-hydroxy-2-methylphenyl) arachidonoyl amide (VDM11), (5Z,8Z,11Z,14Z)-N-(3-furanylmethyl)-5,8,11,14-eicosatetraenamide (UCM707) and (9Z)-N-[1-((R)-4-hydroxybenzyl)-2-hydroxyethyl]-9-octadecen-amide (OMDM2)] and the related compound arvanil on C6 glioma cell viability were investigated. All five compounds reduced the ability of the cells to accumulate calcein, reduced the total nucleic acid content and increased the activity of lactate dehydrogenase recovered in the cell medium. AM404 (10 microm) and VDM11 (10 microm) acted rapidly, reducing cell viability after 3 h of exposure when cell densities of 5,000 per well were used. In contrast, UCM707 (30 microm), OMDM2 (10 microm) and the related compound arvanil (10 microm) produced a more slowly developing effect on cell viability, although robust effects were seen after 6-9 h of exposure. At higher cell densities, the toxicities of AM404 and UCM707 were reduced. Comparison of the compounds with arachidonic acid, arachidonic acid methyl ester, AEA, arachidonoyl glycine and oleic acid suggested that the toxicity of the arachidonoyl-based compounds was related primarily to the acyl side-chain rather than the head group. A variety of pre-treatments blocking possible metabolic pathways and receptor targets were tested, but the only consistent protective treatment against the effects of these compounds was the antioxidant N-acetyl-L-cysteine. It is concluded that AM404, VDM11, UCM707 and OMDM2 produce a rapid loss of C6 glioma cell viability over the same concentration range as is required for the inhibition of AEA uptake in vitro, albeit with a longer latency. Such effects should be kept in mind when acyl-derived compounds are used to probe the function of the endocannabinoid system in the CNS, particularly in chronic administration protocols.

Acylation↗
PubMed1979

Arprinocoid evaluation in broiler chicken pen trials in Europe.

The effect of arpinocid (9-[2-chloro-6-fluorophenyl)methyl]-9H-purin-6-amine) on artificial and natural coccidial infections in broiler chickens was evaluated in a series of pen trials conducted in England, France, and Germany. In trials with induced infections, mortality attributable to coccidiosis did not occur at 50, 60, and 70 ppm although it ranged from 3.2 to 9% in unmedicated groups. At 7 to 8 weeks of age, birds receiving arprinocoid in feed at levels of 40, 50, 60, and 70 ppm had improved body weights and feed conversion compared with unmedicated birds, the differences being significant (P is less than .05) in 4 out of 5 trials. Productivity of birds on arprinocid was equivalent or significantly superior (P is less than 0.5) to those on halofuginone (3 ppm), monensin (100 ppm), nicarbazin (125 ppm), and PANCOXIN (165 ppm). Based on the results of these pen trials, arprinocid at levels of 50 to 70 ppm in feed is a highly efficacious compound for the prophylaxis of coccidiosis, preventing mortality, and permitting good growth and feed conversion under conditions of both mild and severe infection pressure.

Adenine↗
PubMed2002

Stereospecific substitution of enantiomerically pure 1-(2-pyridinyl)ethyl methanesulfonate with beta-dicarbony compounds.

The alkylation of the sodium salt of the malonic acid diester with (R)-1-(2-pyridinyl)ethyl methanesulfonate (2) gave the dimethyl (R)-[1-(2-pyridinyl)ethyl]malonate (3a), stereospecifically. The alkylation reaction of methyl acetoacetate gave the methyl (2'S,2R/2S)-3-oxo-2-[1-(2-pyridinyl)ethyl]butanoate (3d) along with the methyl (S)-3-[1-(2-pyridinyl)ethoxy]-2-butenoate (4d). The acid hydrolysis and decarboxylation of 3d under acidic conditions gave (R)-4-(2-pyridinyl)pentan-2-one (6), and the alkylation of methyl (R)-[1-(2-pyridinyl)ethyl]acetoacetate with benzyl bromide gave a mixture of C-benzylated and O-benzylated products 7 and 8.

Acetylene↗
PubMed1979

[Oxidative degradation of dibenzylsulfide].

Dibenzylsulfid (DBS) as a model of the organic sulfur compounds in crude oil was converted by a mixed culture (containing Pseudomonas aeruginosa) into several water soluble organic substances. Whereas these compounds are detectable with DC- and IR-spectroscopic techniques, benzylmercaptoacetic acid (BMA) was the only isolated product of DBS utilization. Efficiency of degradation, respectively, accumulation of BMA were dependent on aeration and pH-regulation.

Acetates↗
PubMed1994

Inhibitors of the conformational switch involved in CD4 binding by the env glycoprotein gp120 from human immunodeficiency virus type 1 (HIV1).

A 15-residue fragment within the major continuous domain of gp120 from HIV1 that can bind independently to the CD4 receptor conserves the property of behaving as a polarity-triggered conformational switch despite displaying over 50% variability between strains. As this switch behavior (the ability to flip abruptly from beta-sheet to alpha-helix as the medium polarity is lowered past a critical point) is closely linked to CD4-binding ability, it presents a potential strain-independent target for intervention. A number of compounds have been tested for their ability to function as switch inhibitors. All those that displayed switch inhibitory activity also have been shown to act to prevent CD4 binding and/or viral infectivity. In addition, all compounds testing positive as switch inhibitors have certain chemical characteristics in common. The groundwork has thus been established for the design of strain-independent blockers of CD4 binding based on the strategy of switch inhibition.

Amino Acid Sequence↗
PubMed1975

Cycloalkanones. 7. Hypocholesterolemic activity of aliphatic compounds related to 2,8-dibenzylcyclooctanone.

A series of 19 aliphatic analogs of 2,8-dibenzylcyclooctanone and 1,5-diphenyl-2,4-dimethyl-3-pentanone was examined. Separation of hypocholesterolemic activity from the previously observed uterotropic and antifertility activities was achieved by simplification of the parent compound to 2-octanone. There was no loss of hypocholesterolemic activity. Reduction of serum cholesterol levels in male rats to less than 50% of control values was obtained at a dose of 10 mg/kg/day.

Animals↗
PubMed2004

[Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation].

Essential oils were extracted from Myristica fragrans Houtt. by supercritical fluid extraction (SFE) and steam distillation (SD). Their components were analyzed by gas chromatography-mass spectrometry and compared. 48 compounds were identified for the essential oil extracted by supercritical carbon dioxide, and its main components have been found to be myristic acid, myristicin, terpinen-4-ol, alpha-pinene and safrole. 38 compounds were identified for the essential oil obtained by SD, and its main components have been found to be beta-pinene, terpinen-4-ol, alpha-pinene, gamma-terpinene and beta-phellandrene.

Allylbenzene Derivatives↗
PubMed1999

The effect of N-substituted alkyl groups on anticonvulsant activities of N-Cbz-alpha-amino-N-alkylglutarimides.

In order to examine the effects of N-substituted alkyl group on the anticonvulsant activities of N-Cbz-alpha-aminoglutarimides as novel anticonvulsants with broad spectrum, a series of (R) or (S) N-Cbz-alpha-amino-N-alkylglutarimides (1 and 2) were prepared from the corresponding (R) or (S) N-Cbz-glutamic acid and evaluated for the anticonvulsant activities in the maximal electroshock seizure (MES) test and pentylenetetrazol induced seizure (PTZ) test, including the neurotoxicity. The most potent compound in the MES test was (S) N-Cbz-alpha-amino-N-methylglutarimide (ED50=36.3 mg/kg, PI=1.7). This compound was also most potent in the PTZ test (ED50=12.5 mg/kg, PI=5.0). The order of anticonvulsant activities against the MES test as evaluated from ED50 values for (R) series was N-methyl > N-H > N-ethyl > N-allyl; for the (S) series N-methyl > N-H > N-ethyl > N-allyl > N-isobutyl compound. Against the PTZ tests, the order of anticonvulsant activities showed similar pattern; for the (R) series, N-methyl > N-H > N-ethyl > N-allyl; for the (S) series N-methyl > N-H > N-ethyl > N-allyl > N-isobutyl compound. From the above results, N-substituted alkyl groups were thought to play an important role for the anticonvulsant activities of N-Cbz-alpha-amino-N-alkylglutarimides.

Animals↗
PubMed2004

N-Benzylindole-2-carboxylic acids: potent functional antagonists of the CCR2b chemokine receptor.

Screening of the corporate database led to the discovery of a novel series of N-benzylindole-2-carboxylic acid CCR2b chemokine receptor antagonists. These compounds demonstrate high affinity and functional inhibition of the CCR2b receptor. A discussion of the structure-activity relationships is presented, together with evidence for a highly selective receptor binding profile.

Benzyl Compounds↗
PubMed2002

Structure-activity relationships of methoctramine-related polyamines as muscular nicotinic receptor noncompetitive antagonists. 2. Role of polymethylene chain lengths separating amine functions and of substituents on the terminal nitrogen atoms.

Polymethylene tetraamine methoctramine (1) is a prototypical antimuscarinic ligand endowed with a significant affinity for muscular nAChRs. Thus, according to the universal template approach, structural modifications were performed on 1 in order to improve affinity and selectivity for the muscle-type nAChR. The polyamine derivatives synthesized were tested at both frog rectus and Torpedo nAChRs and at guinea pig left atria (M(2)) and ileum longitudinal muscle (M(3)) mAChRs. All of the compounds, like prototype 1, were noncompetitive antagonists of nicotinic receptors while being competitive antagonists at M(2) and M(3) mAChRs. The biological profile of polyamines 4-7 revealed that increasing the number of amine functions and the chain length separating these nitrogen atoms led to a significant improvement in potency at nAChRs. Moreover, the role of the number and type of amine functions in the interaction with nAChRs was further investigated through the synthesis of compounds 9 and 10. Tetraamines 8 and 11, bearing a rather rigid spacer between the nitrogen atoms instead of the very flexible polymethylene chain, displayed a profile similar to that of 1 at nAChRs, whereas a significant decrease in potency was observed at mAChRs. Tetraamine 12, bearing a 2-methoxyphenethyl group, was less potent than 1, whereas tetraamine 13, carrying a diphenylethyl moiety, was more potent than 1, confirming that an increase in size of the hydrophobic group on the terminal nitrogen atoms increases significantly the binding affinity for nAChRs. Tetraamines 14-17 were significantly more potent than prototype 2 at both frog rectus and Torpedo nAChRs, confirming that an increase in the distance between the amine functions results in a parallel increase in the affinity for nAChRs. To gain insight into the mode of interaction of polymethylene tetraamines with nAChRs, photolabile (19 and 20) and fluorescent (21 and 22) compounds were synthesized. A most intriguing finding was the observation that 19, which bears two identical azido groups on the terminal nitrogen atoms, was found to bind the Torpedo nAChR with a 1:1 stoichiometry, suggesting a U-shaped conformation in the receptor interaction. Moreover, the high potency shown by fluorescent compounds 21 and 22 appears promising for a further characterization of the polymethylene tetraamines binding site with the muscle-type nAChR.

Animals↗
PubMed2002

Indazole inhibition of cystic fibrosis transmembrane conductance regulator Cl(-) channels in rat epididymal epithelial cells.

Previous studies have shown that two indazole compounds, lonidamine [1-(2,4-dichlorobenzyl)-indazole-3-carboxylic acid] and its analogue AF2785 [(1-(2,4-dichlorobenzyl)-indazol-3-acrylic acid], suppress fertility in male rats. We also found that these compounds inhibit the cystic fibrosis transmembrane conductance regulator chloride (CFTR-Cl(-)) current in epididymal epithelial cells. To further investigate how lonidamine and AF2785 inhibit the current, we used a spectral analysis protocol to study whole-cell CFTR current variance. Application of lonidamine or AF2785 to the extracellular membrane of rat epididymal epithelial cells introduced a new component to the whole-cell current variance. Spectral analysis of this variance suggested a block at a rate of 3.68 micro mol(-1)/sec(-1) and an off rate of 69.01 sec(-1) for lonidamine, and an on rate of 3.27 micro mol(-1)/sec(-1) and an off rate of 108 sec(-1) for AF2785. Single CFTR-Cl(-) channel activity using excised inside-out membrane patches from rat epididymal epithelial cells revealed that addition of lonidamine to the intracellular solution caused a flickery block (a reduction in channel-open time) at lower concentration (10 micro M) without any effect on open channel probability or single-channel current amplitude. At higher concentrations (50 and 100 micro M), lonidamine showed a flickery block and a decrease in open-channel probability. The flickery block by lonidamine was both voltage-dependent and concentration-dependent. These results suggest that lonidamine and AF2785, which are open-channel blockers of CFTR at low concentrations, also affect CFTR gating at high concentrations. We conclude that these indazole compounds provide new pharmacological tools for the investigation of CFTR. By virtue of their interference with reproductive processes, these drugs have the potential for being developed into novel male contraceptives.

Animals↗