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Results for “Thiophenes”

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At least 19 recordsLinked to original sources
PubMedDate not supplied

The metabolism of alpha-aminobenzo(b)thiophene-3-propionic acid (the sulfur analog of tryptophan) in the rat.

The biotransformation of 3H-labeled alpha-aminobenzo[b]thiophene-3-propionic acid (the sulfur analog of tryptophan) was investigated in rats. Forty-eight hours after ip administration, 80% of the radioactive dose was recovered in the urine and 5% in the feces; tissue levels of radioactivity accounted for the remainder of the administered dose. The urinary metabolites were identified by a combination of thin-layer chromatography, gas chromatography, and gas chromatography-mass spectrometry, and were quantitated by thin-layer chromatography and liquid-scintillation counting to give, as percentages of the administered dose, unchanged alpha-aminobenzo[b]thiophene-3-propionic acid (20.6%), benzo[b]thiophene-3-acetic acid (1.3%), benzo[b]thiophene-3-pyruvic acid (14.2%), benzo[b]thiophene-3-lactic acid (4.9%), and N-(benzo[b]thiophene-3-acetyl)glycine (46.2%).

Animals↗
PubMed1978

Effects of thiophene analogues of chloroamphetamines on central serotonergic mechanisms.

Ring-chlorinated thienylisopropylamines, thiophene analogues of chloroamphetamines, have been synthesized and their effects on serotonergic mechanisms in the rat brain have been evaluated. With 4,5-dichlorothienylisopropylamine (3e), a pharmacological profile similar to that of p-chloroamphetamine, consisting in a marked and long-lasting serotonin depletion and a rather strong and prolonged inhibition of synaptosomal uptake of serotonin, was found. Chloro substitution in position C3 of the thiophene ring did not determine brain serotonin depletion nor serotonin uptake inhibition but enhanced brain MAO inhibitory activity present in all these compounds. 3,5-Dichlorothienylisopropylamine (3g) was the only compound of the series in which the inhibition of serotonin uptake was more marked than the serotonin depleting property.

Amphetamines↗
PubMed1978

Thiophene analogues of the carcinogens benzidine and 4-aminobiphenyl: evaluation in vitro.

A biologically active molecule with one or more aromatic rings often retains its activity when one of these rings is replaced by an isosteric and/or isoelectronic aromatic ring. Consideration has been given to whether this effect can be expected to apply to aromatic organic carcinogens. The literature relevant to this topic has been reviewed and the thiophene analogues of the carcinogens benzidine and 4-aminobiphenyl have been synthesized and evaluated for potential carcinogenicity. The compounds prepared were 5-p-acetamidophenyl-2-thiophenamine hydrochloride (XIII), 5-phenyl-2-thiophenamine hydrochloride (XIV), N-(5-p-acetamido-phenylthiophen-2-yl)acetamide (XV) and N-(5-phenylthiophen-2-yl)-acetamide (XVI) (see Chart for structures). Each compound was evaluated in the Salmonella reverse-mutation assay of Ames and the cell-transformation assay of Styles. The activity profiles observed for these compounds in vitro were consistent with their known chemistry, and indicate potential carcinogenicity. However, their overall chemical and biological behaviour casts doubt upon whether they would be capable of eliciting tumours in vivo. Because it is important to establish the degree of reliance which can be placed upon in vitro predictions of potential carcinogenicity generated for structurally new compounds, one of the thiophene derivatives, N-(5-phenylthiophen-2-yl)acetamide ((XVI), is currently being evaluated for carcinogenicity in mice.

Aminobiphenyl Compounds↗
PubMedDate not supplied

Effects of thiophene on the Purkinje cell dendritic tree: a quantitative Golgi study.

A quantitative analysis was made of alterations in the dentritic organisation of Purkinje cells in the cerebellum of the adult rat following the administration of the degranulating agent, thiophene. This substance completely eliminated the granule cell population in a number of regions of cerebellar cortex. Purkinje cell dentdritic trees in these regions were markedly reduced in size when compared with control cells and provided evidence for a non-random loss of dentritic segments. Other dendritic abnormalities were noted. These results were discussed in relation to current theories of neuronal maintenance, and the feasibility of using toxic degranulating agents, such as thiophene, was considered.

Animals↗
PubMed1977

Comparison of strains of Mycobacterium tuberculosis from British, Ugandan and Asian immigrant patients: a study in bacteriophage typing, susceptibility to hydrogen peroxide and sensitivity to thiophen-2-carbonic acid hydrazide.

Strains of Mycobacterium tuberculosis were obtained from 65 patients with pulmonary tuberculosis resident in Uganda, and from pulmonary and extrapulmonary tuberculosis in 42 British patients of European ethnic stock and in 67 Asian immigrants, often from Uganda, resident in Britain. The bacteriophage-type patterns of the African, British and Asian strains were different. The pattern for the Asian strains resembled that found previously in patients from South India, suggesting that there has been little interchange of organisms between the Asian community and the African and British communities alongside whom they have lived. The patterns for pulmonary and extra-pulmonary tuberculosis were similar. Strains of bacteriophage type 1, mainly obtained from Asians, were characterized by a greater susceptibility to the bactericidal activity of hydrogen-peroxide and/or a greater sensitivity to thiophen-2-carbonic acid hydrazide than strains of other types.

Asia↗
PubMed1979

Phototoxic polyacetylenes and their thiophene derivatives. (Effects on human skin).

Polyacetylenes and their thiophene derivatives were tested for their effects on human skin. Topically applied alpha-terthienyl evoked bi-phasic phototoxic dermatitis and the appearance of 'sunburn' cells in human epidermis. None of 11 polyacetylenes had the same effect although they mimicked alpha-terthienyl in their phototoxic effects on Candida albicans and certain pathogenic microorganisms. The UV-mediated antibiotic activity of the compounds and their apparent lack of phototoxicity towards the skin suggest a potential topical therapeutic role for them in yeast, fungal and bacterial infections and light-responsive dermatoses. Their topical sensitizing capacity, however, has not yet been studied.

Alkynes↗
PubMed1978

Suppression of calcific fibrous-fatty plaque formation in rabbits by agents not affecting elevated serum cholesterol levels. The effect of thiophene compounds.

We tested the suppressive effect of antihypercalcemic-hyperphosphatemic agents on atherogenesis. We studied five groups of rabbits for 8 weeks, one control group and four groups on a fibrogenic atherogenic diet. One group received the atherogenic diet alone, and the remaining three atherogenic groups were treated simultaneously with 2-thiophenecarboxylic acid (ThCA), 5-methyl-2-thiophenecarboxylic acid (5-CH3-ThCA), and 5-bromo-2-thiophenecarboxaldehyde (5-Br-ThCA). Rabbits receiving the atherogenic diet alone developed: (1) elevations of serum cholesterol, calcium, and phosphorus; (2) massive fibrous-fatty aortic plaques with excessive accumulation of aortic collagen, elastin, and lipids; (3) marked deposition of calcium and phosphorus in both aortic tissue and elastin; and (4) severe lipid infiltration of the liver. Treatment with all three drugs normalized the elevated serum calcium but not the cholesterol levels, and effectively inhibited all aspects of the atherosclerotic process as determined morphologically and biochemically. The order of effectiveness was: 5-CH3-ThCa greater than 5-Br-ThCA greater than ThCA. No bone resorption occurred in the treated groups. The normalizing effects of the thiophene compounds on serum phosphorus levels were not significant at the dosages used.

Animals↗
PubMed1975

A potentially antianginal benzo [b]thiophene with an amiodarone-like haemodynamic profile.

L 9146 or 2-methyl-3(3,5 dimethyl-4-gamma-di-n-butylaminopropoxy-benzoyl)-benzo [b] thiophene is a substance belonging to the amiodarone series which induces in the anaesthetized dog a decrease of myocardial oxygen consumption which is mainly due to slowing of the heart rate and reduction in systemic blood pressure. L 9146 also enhances coronary blood flow. L 9146 has also antiadrenergic properties since catecholamine-induced hypertension, tachycardia and increase of myocardial oxygen consumption are markedly antagonized; these antiacrenergic effects are not due to a competitive blockade of the beta-adrenoceptors. L 9146 does not decrease cardiac output, but increases it appreciably in the initial phase of its action. Several findings indicate that when the intensity of certain properties is considered, l9146 is more active than aniodarone since only half the dose used with aniodarone is required to achieve a given level of action. The overall haemodynamic properties of L 9146, which are similar to those of amiodarone, are considered to be potentially valuable for the long-term treatment of angina pectoris.

Adrenergic beta-Antagonists↗
PubMed1978

Pyrrole, furan, and thiophene oxamates as potential antiallergy agents.

Nine heterocyclic oxamic acid derivatives were synthesized and tested in the rat passive cutaneous anaphylactic assay as potential antiallergy agents. Some compounds also were tested for their effects on cholesterol-lipoprotein levels and for diuretic, antidiabetic, and antifertility activities in rats.

Amino Acids↗