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PubMed1988

[UV-spectrophotometry in drug control. 39. Spectrophotometric behavior of substances with chromophores and auxochromes in aliphatic chains, in saturated heterocyclics and the heterocyclic compounds: furan, imidazole, thiazole, thiadiazole and oxadiazole].

The spectra of 22 drug substances with chromophores and auxochromes in the aliphatic chain, in the saturated heterocyclus and in heterocyclic compounds (furan, imidazole, thiazole, thiadiazole and oxadiazole) underwent a systematic investigation and the results obtained were evaluated. Influences of substituents and solvents on shifts of the E, K, B and R bands were discussed.

Chemical Phenomena↗
PubMed1987

Synthesis of thiazole derivatives with positive inotropic effect.

Thiazole derivatives with potential positive inotropic effect were synthesized. The highest activity (medium positive inotropic effect) was exhibited by ethyl 2-(2-hydroxyethylamino)-4-phenylthiazole-5-carboxylate (3b) of which several derivatives have been prepared. Among these derivatives only those which could presumably easily removed in the living organism to give 3b exhibited a medium positive inotropic effect (6, 8b). It was assumed that the effect of 3b had a beta-agonist character.

Animals↗
PubMed1985

Novel thiazolidine-2,4-dione-4-thiosemicarbazone and 4-[(3,4-diaryl-3H-thiazol-2-yl)azo]thiazolidin-2-one derivatives: synthesis and evaluation for antimicrobial and anticancer properties.

Two novel series of 3-benzylthiazolidine-2,4-dione-4-thiosemicarbazones (V - IX) and 3-benzyl-4-[(3,4-diaryl-3H-thiazol-2-yl)azo]thiazolidin-2-on es (X - XXII) were synthesized as potential antimicrobial and anticancer agents. The products were found to be inactive against a variety of microorganisms and the preliminary antileukemic evaluation of some representative compounds against P 388 lymphocytic leukemia indicated insignificant activity.

Animals↗
PubMed1983

Peroxidase metabolism of the urinary bladder carcinogen 2-amino-4-(5-nitro-2-furyl)thiazole.

Metabolism of 2-amino-4-(5-nitro-2-furyl)thiazole (ANFT) by a variety of different peroxidases was examined. Metabolism of ANFT was measured by the binding of radiolabeled substrates to protein and DNA. Prostaglandin hydroperoxidase but not horseradish peroxidase, lactoperoxidase, or chloroperoxidase metabolically activated ANFT. All four peroxidases catalyzed the binding of benzidine to protein and DNA. With peroxide substrates, peroxidase-catalyzed binding of both carcinogens was observed with or without molecular oxygen. Arachidonic acid-dependent binding of ANFT and benzidine by prostaglandin endoperoxide synthetase was inhibited by anaerobic conditions and aspirin. Chloroperoxidase activation of benzidine was also inhibited by aspirin. Vitamin E inhibited activation of both carcinogens by all enzymes examined. Prostaglandin hydroperoxidase-catalyzed binding of benzidine to protein was inhibited by the 5-nitrofurans ANFT and 3-hydroxymethyl-1-(([3-(5-nitro-2-furyl)allydidene] amino))hydantoin and acetaminophen, while only acetaminophen inhibited horseradish peroxidase-catalyzed binding. These results indicate that different peroxidases may exhibit specificity with respect to their activation of carcinogens. Only prostaglandin hydroperoxidase activated the 5-nitrofuran ANFT, while a number of peroxidases activated the aromatic amine benzidine.

Anaerobiosis↗
PubMed1984

Bioconversion and macromolecular binding of 2-amino-4-(5-nitro-2-furyl)thiazole by cultured rat urothelial cells.

Bioconversion and binding of 2-amino-4-(5-nitro-2-furyl)-thiazole (ANFT) were examined using cultured rat bladder epithelial cells from weanling male F344 rats. Bladder cells were obtained in large quantities from outgrowths of dissected explants which were grown on collagen gels. Metabolic potential of rat urothelial cells to activate ANFT was evaluated by incubating primary culture cells with [2-14C]ANFT for 48 hr. Metabolites were subsequently analyzed by chromatographic and spectroscopic methods. Thin-layer chromatography of the ethyl acetate:diethyl ether (1:1, v/v) extract of the culture medium revealed two regions of radioactivity with Rf values of 0.12 and 0.60, the former corresponding to ANFT and the latter to one of its metabolites. High-pressure liquid chromatography of the solvent extract revealed two major peaks, with retention times of about 4 and 9 min, corresponding with the metabolite and ANFT, respectively. Low-resolution mass spectrum of the isolated metabolite showed a molecular ion at m/e 181. The metabolite was identified as 1-[4-(2-aminothiazolyl)]-3-cyano-1-propanone based on its chromatographic and spectral characteristics in comparison with the synthetic compound. About 24% of the recovered radioactivity from the culture medium was extractable into the organic phase, a majority of which was identified as 1-[4-(2-aminothiazolyl)]-3-cyano-1-propanone. Analysis of binding to proteins and nucleic acids prepared following exposure of [2-14C]ANFT revealed a 15- and 9-fold greater amount of binding, respectively, in cultures incubated with bladder cells than their corresponding heat-inactivated controls. Furthermore, homogenates of cultured bladder cells reduced ANFT on anaerobic incubation with reduced nicotinamide adenine dinucleotide phosphate to generate 1-[4-(2-aminothiazolyl)]-3-cyano-1-propanone. On reduction of [2-14C]ANFT with rat bladder or liver homogenates, about 23 and 11%, respectively, of the initial amounts of radioactivity were bound to the trichloracetic acid-insoluble fraction. These data demonstrate that rat bladder cells possess the metabolic capability to reduce ANFT and to generate reactive intermediate(s) that bind to cellular macromolecules.

Animals↗
PubMed1984

Medial smooth muscle cell proliferation in the balloon injured rabbit aorta: effect of a thiazole compound with platelet inhibitory activity.

Twenty-seven adult male New Zealand rabbits (3-4 kgs) were used in this study. Six rabbits received vehicle, 3 groups of 6 each received doses of 4,5-bis(p-methoxyphenyl)-2-(trifluoromethyl)-thiazole, (U-53,059), at 0.3 mg/kg, 3.0 mg/kg and 30.0 mg/kg/day respectively. Drug and vehicle doses were given orally each day starting 3 days before balloon injury and continuing for the entire 2 week time period. Three rabbits were used as nontreated sham controls. In the vehicle and U-53,059 treated groups aortae were denuded of endothelial cells by balloon catheter injury. Two weeks after injury platelet aggregation to collagen was measured and the aortae removed for analysis of surface characteristics by scanning electron microscopy and lesion size by morphometry. All doses of U-53,059 inhibited platelet aggregation. The 3.0 and 30.0 mg/kg groups had the greatest inhibitory effect. All balloon injured aortae had the same morphologic characteristics. All vessels had similar extent and intensity of Evan's blue staining, similar areas of leukocyte/platelet adhesion, and a myointimal cell cover of transformed smooth muscle cells. The myointimal proliferative response was not inhibited at any of the drug doses studied.

Animals↗
PubMed1981

Prostaglandin hydroperoxidase-mediated 2-amino-4-(5-nitro-2-furyl) [14C]thiazole metabolism and nucleic acid binding.

Prostaglandin hydroperoxide-mediated metabolism and binding of 2-amino-4-(5-nitro-2-furyl) [14C]thiazole ([14C]ANFT) metabolite to nucleic acids and proteins were investigated with rabbit bladder transitional epithelial and solubilized ram seminal vesicle microsomes. Metabolism was assessed by spectrophotometric and radiochemical techniques. Substrate and inhibitor studies are consistent with both metabolism and binding of [14C]ANFT occurring by the prostaglandin hydroperoxidase activity of prostaglandin endoperoxide synthetase. The ratio of the rates of [14C]ANFT product formation is approximately 3:7:10 (organic soluble:non-trichloroacetic acid precipitable: trichloroacetic acid precipitable) over a wide range of arachidonic acid concentrations. Approximately 2 and 1% of the total [14C]ANFT metabolized binds to transfer RNA and DNA, respectively. The metabolite isolated from the organic phase had a chromatographic profile and ultraviolet spectra different from authentic ANFT. If transfer RNA or DNA is added at the end of a 5-min incubation, no binding to nucleic acids was observed. The demonstration of prostaglandin hydroperoxidase-mediated covalent binding to nucleic acids is consistent with the involvement of this enzyme in 5-nitrofuran-induced bladder carcinogenesis.

Animals↗
PubMed1981

Mutagenicity, carcinogenicity, distribution, and nitroreduction of 4-(5-nitro-2-furyl)thiazole in the rat.

Albino noninbred weanling female Sprague-Dawley rats were fed a powdered basic grain diet (Group 1) or a basic diet supplemented with 1540 ppm of 4-(5-nitro-2-furyl)thiazole (NFT) (Group 2). Group 2 rats consumed an estimated mean NFT cumulative dose of 42 mmol/rat, exhibited significant growth retardation and hepatomegaly, and displayed 46 neoplasms (24 multiple mammary fibroadenomas, 19 forestomach squamous cell carcinomas, and 3 other malignant tumors) in 31 of 35 rats histologically evaluated. Six of 36 control rats had solitary, benign mammary fibroadenomas. After p.o. administration of NFT, extraction of urine with chloroform:diethyl ether followed by gas chromatography provided a major peak with a retention time of about 4 min. Catalytic hydrogenation of NFT with palladium on activated carbon afforded a product with the same retention time. The isolated urinary metabolite of NFT exhibited mass spectral fragmentation patterns and gas and high-pressure liquid chromatographic retention times similar to those of the chemical reduction product. These data demonstrate the identical chemical characteristics of the in vivo urinary metabolite of NFT and the compound obtained by chemical reduction of NFT. Spectroscopic analyses established the structural identity of this reduced product as 1-(4-thiazolyl)-3-cyano-1-propanone. Forty-eight hr after the intragastric administration of [14C]NFT, 32% of radioactivity was recovered in urine, 57% was recovered in gastrointestinal contents and feces, and 5.5% was recovered in expired 14CO2. About 2% of the urinary radioactivity was extracted in chloroform:diethyl ether, suggesting that 1-(4-thiazolyl)-3-cyano-1-propanone is quantitatively a minor urinary metabolite of NFT. 1-(4-Thiazolyl)-3-cyano-1-propanone was 1.1 x 10(4)-fold less active than was NFT in the Ames mutagenicity assay with Salmonella typhimurium TA 100.

Animals↗
PubMedDate not supplied

Synthesis of imidazo[2,1-b]thiazoles and thiazolines as potential antiulcer agents.

The replacement of the imidazole ring of cimetidine with a bicyclic system (imidazo[1,2-a]pyridine), reported in the literature, produced compounds endowed with potent antiulcer activity. In this paper we describe the synthesis of imidazo [2,1-b]thiazoles and thiazolines bearing the side chain of metiamide, cimetidine and ranitidine: the compounds obtained, tested on gastric lesions induced in rats by ethanol and by stress, were devoid of antiulcer activity.

Animals↗
PubMed1994

Use of thiazole orange homodimer as an alternative to ethidium bromide for DNA detection in agarose gels.

Detection of polymerase chain reaction-amplified DNA fragments is commonly accomplished by visualizing the products in electrophoretic agarose beds with the use of ethidium bromide under ultraviolet light. However, ethidium bromide is mutagenic, and special handling and disposal precautions must be used. We report the use of a nonmutagenic dye, thiazole orange dimer (TOTO), which can be substituted for ethidium bromide. The excitation maximum for TOTO under ultraviolet light is 488 nm, and the absorption maximum is 510 nm, necessitating photographic filters different from those used for ethidium bromide for optimal results. Of particular importance in TOTO's use is the quantity used for each gel lane, since excess TOTO will cause unacceptable product mobility retardation. TOTO is only slightly more expensive than ethidium bromide. Overall, this stain provides very good visualization of polymerase chain reaction--amplified DNA bands in agarose gels. We believe the use of this safer reagent will become more widespread with increased regulation of laboratory activities.

Base Sequence↗
PubMed1993

Antiinflammatory activity of aminoketone derivatives of 2,4-disubstituted thiazoles.

A group of nine aminoketones, 2,4-disubstituted thiazole derivatives were tested in vivo in order to evaluate their biological activity. Antiinflammatory activity was studied by means of the carrageenin-induced mouse paw edema. Writhing induced by acetic acid in rats used to evaluate the analgesic activity. The results are discussed from the view of structure activity relationship.

Analgesics↗
PubMed1996

Prevention of platelet-activating factor-induced gastrointestinal lesions in rats by the new specific antagonist N-(2-dimethylaminoethyl)-N-(3-pyridinylmethyl)[4-(2,4,6-triisopropylphe nyl) thiazol-2yl]amine.

SR 27417 (CAS 136468-36-5, N-(2-dimethylaminoethyl)-N-(3-pyridinylmethyl)[4-(2,4,6-triisop ropylphenyl) thiazol-2-yl]amine), a highly potent platelet-activating factor (PAF) receptor antagonist, was tested for its ability to prevent macroscopic and histologically assessed gastrointestinal (GI) lesions in rats induced by PAF as compared to the reference compound apafant. Both compounds were orally effective but SR 27417 prevented the gut lesioning effects of PAF at lower doses than apafant. In addition, a dose of apafant (1.5 mg/kg) that showed almost maximal effect when given 30 min before PAF, had lost most of its protective action by 3 h, while SR 27417 at a comparably effective dose (0.5 mg/kg) retained substantial ability to prevent gut lesions in all the GI tract segments investigated, 18 h after administration. These findings suggest that SR 27417 is a potent and long lasting inhibitor of PAF-induced gastrointestinal lesions in rats.

Animals↗
PubMed1997

Anti-HIV agents. V. Synthesis, structure and in vitro anti-HIV activity of novel 1H,3H-naphtho[2',3':4,5]imidazo[1,2-c]thiazoles.

A series of 1H,3H-naphtho[2',3':4,5]imidazo[1,2-c]thiazoles, TBZ analogues, was prepared in order to explore the influence on anti-HIV activity of the spatial requirements of the hydrophobic moiety fused to imidazothiazole system. In spite of a butterfly-like conformation evidenced by X-ray analysis of compound 4g, the results of in vitro screening suggest that the replacement of the benzene fused ring by the naphthyl moiety negatively influences the activity of analogous thiazolobenzimidazole derivatives, some of which are potent non-nucleoside HIV-1 RT inhibitors.

Anti-HIV Agents↗
PubMed1999

2,4-Disubstituted thiazoles, Part III. Synthesis and antitumor activity of ethyl 2-substituted-aminothiazole-4-carboxylate analogs.

The synthesis of several new ethyl 2-substituted-aminothiazole-4-carboxylate analogs is described. The prepared compounds were tested for their in vitro antitumor activity against 60 human tumor cell lines by the National Cancer Institute (NCI) and showed potential anticancer activity. Ethyl 2-[3-(diethylamino)-propanamido]-thiazole-4-carboxylate (14) exhibited remarkable activity against RPMI-8226 leukemia cell line with GI50 value of 0.08 microM, and a broad spectrum activity against all the tumor cell lines used with GI50 (MG-MID) value of 38.3 microM. The detailed synthesis and antitumor screening data are reported.

Antineoplastic Agents↗