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PubMed1976

Neighbouring acetamido-group participation in reactions of derivatives of 2-acetamido-2-deoxy-D-glucose.

Kinetic measurements suggest that neighbouring acetamido-group participation occurs in the spontaneous hydrolysis and methanolysis of o-carboxyphenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside and in the spontaneous hydrolysis of 2,4-dinitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside and 2-acetamido-2-deoxy-beta-D-glycopyranosyl fluoride. The methanolyses of these compounds proceed with predominant retention of configuration which is also consistent with neighbouring acetamido-group participation. The oxazoline intermediate which would arise from such a process was detected during methanolysis of 2-acetamido-2-deoxy-beta-D-glucopyranosyl fluoride in the presence of bases by n.m.r., i.r., and u.v. spectroscopy. Attempts to isolate the oxazoline were unsuccessful.

Acetylglucosamine↗
PubMed1975

Synthesis and spectral properties of cytosine nucleosides of 2-amino-2-deoxy-alpha-D-arabino-furanose and -pyranose.

Ethyl 2-deoxy-3,5-di-O-p-nitrobenzoyl-1-thio-2-(trifluoroacetamido)-beta-D-arabinofuranoside (3) was converted into the glycosyl chloride. Condensation of the latter with 2,4-dimethoxypyrimidine, followed by amination, gave 1-(2-amino-2-deoxy-alpha-D-arabinofuranosyl)cytosine (6), which was also obtained from the alpha-D anomer (4) of 3. Similarly, 1-(2-amino-2-deoxy-alpha-D-arabinopyranosyl)cytosine (12) was synthesized from ethyl 2-deoxy-3,4-di-O-p-nitrobenzoyl-1-thio-2-(trifluoroacetamido)-alpha-D-arabinopyranoside (9). The p.m.r. spectra of these nucleosides, as well as those of the 1-thioglycosides, are discussed in terms of the conformation of the sugar portion. In particular, a large change of the J1,2 coupling constants of the alpha-D-furanosides, according to the substituents at C-1 and C-2, was interpreted on the basis of conformational mobility.

Arabinose↗
PubMed2001

Separation of six uremic middle molecular compounds by high performance liquid chromatography and analysis by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.

BACKGROUND: Since the postulation of uremic middle molecule (UMM) hypothesis made by Babb et al. [Trans-Am Soc Artif Intern Organs 18 (1972) 98], there has been great interest in the separation and identification of the role of UMM. However, few of the compounds isolated from UMM fractions were demonstrated to play an important role in humans. Thus, the separation and identification of the real UMM is essential for UMM research. METHODS: Urine and serum samples from uremic patients and healthy subjects were separated by gel permeation chromatography. Two presumed UMM fractions, A and B, were obtained from uremic sera and urine, normal urine, but not normal sera. Fraction A was further isolated by anion exchange chromatography and a series of sub-peaks were obtained. The sub-fraction A-3 obtained in the second step was desalted on a Sephadex G-15 column, and characterized by IR, UV and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS). Further separation of sub-fraction A-3 was performed by high performance liquid chromatography (HPLC). RESULTS: By gel permeation chromatography, two UMM peaks (A and B) were detected at 206 nm in normal urine, uremic sera, but they were barely noticed in the profile of normal sera. In contrast, the absorption at 206 nm of fractions A and B from uremic serum and urine were smaller than that of fractions A and B from normal urine. Fractions A from different origins were resolved into eight to nine sub-peaks at 230 nm by anion exchange chromatography. One of these sub-peaks, A-3, was detected in uremic serum and normal urine, but is undetectable in uremic urine. After desalting, sub-fraction A-3 was separated into two parts designated as A-3-I and A-3-II. MALDI-TOF-MS revealed that fraction A-3-I and A-3-II from two origins were identical, respectively-fraction A-3-I contained three components with MW 839.69, 1007.94 and 2015.16 and fraction A-3-II consisted of another three components with MW 873.69, 1106.67 and 1680.28. Six middle molecular compounds in sub-fraction A-3 were thoroughly resolved by HPLC. CONCLUSION: Our results demonstrated that the UMM sub-fraction A-3 contains the real UMM in the MW range of 800-2015 Da. By multi-step chromatographic isolation, six real middle molecular compounds were purified and characterized with MALDI-TOF-MS. It is likely that three of these UMM compounds are important, as they readily accumulated in sera of uremic patients, but are normally excreted in healthy subjects.

Adult↗
PubMedDate not supplied

Synthesis of N-[4-(propyl)cyclohexyl]-amides with anti-inflammatory and analgesic activities.

Seventeen (un)substituted N-[4-(propyl)cyclohexyl]-amides (6a-h, 7a-h and 8) were synthesized and tested as anti-inflammatory and analgesic agents. The substituents on the aromatic ring were chosen in order to study the influence of electron-withdrawing or electron-donating residues, that change the electronic density on the aromatic moiety. The pharmacological results allow drawing some preliminary considerations on structure-activity relationships.

Amides↗
PubMed2001

Synthesis and antimicrobial properties of N-substituted derivatives of (E)-4-azachalcones.

Syntheses of 11 new N-bromoalkyl substituted bromides of (E)-4-azachalcone and N-o-(m- and p-) halobenzyl substituted halides of (E)-3'-hydroxy-4-azachalcone of antimicrobial activity are reported. Compounds 3d, 3e, 6b, 6c, and 6e reveal good antimicrobial activity against Staphylococcus aureus and Enterococcus faecalis as well as moderate activity against Escherichia coli and Klebsiella pneumoniae.

Anti-Bacterial Agents↗
PubMed2001

Synthesis and analgesic activity of some 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole derivatives.

In this study, derivatives of 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole were synthesized and their analgesic activity assayed in two tests. 1,2,4,5-Tetrasubstituted imidazole compounds were obtained by the treatment of purified imidazole compounds with benzyl chloride in the presence of sodium hydride. The structure elucidation of the compounds was performed by IR, 1H-NMR and mass spectroscopic data and elemental analysis results. Generally the prepared compound exhibited only moderate analgesic activity in mice at the dose of 100 mg/kg i.p.; however, a few of them exhibited good activity, almost equivalent to that of morphine at 1 mg/kg i.p. was observed. At the above dosage, no toxicity was observed for all compounds.

Analgesics, Non-Narcotic↗
PubMed2002

Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones.

Sixteen 1-(2-naphthyloxyacetyl)-4-substituted-3-thiosemicarbazide, 2-(2-naphthyloxymethyl)-5-substitutedamino-1,3,4-oxadiazole, 2-(2-naphthyloxymethyl)-5-substitutedamino-1,3,4-thiadiazole and 5-(2-naphthyloxymethyl)-4-substituted-1,2,4-triazole-3thione derivatives have been prepared and evaluated as orally active anti-inflammatory agents with reduced side-effects. The structures of the compounds were confirmed by IR and 1H NMR spectral data and microanalysis. The anti-inflammatory and ulcerogenic activities of the compounds were compared with naproxen, indomethacin and phenylbutazone. In carrageenan-induced foot pad edema assay, 2-(2-naphthyloxymethyl)-5-methylamino-1,3,4-oxadiazole, 5-(2-naphthyloxymethyl)-4-methyl-1,2,4-triazole-3-thione and 5-(2-naphthyloxymethyl)-4-ethyl-1,2,4-triazole-3-thione showed an interesting anti-inflammatory activity. In the air-pouch test, 1,3,4-oxadiazole and 1,2,4-triazole-3-thione derivatives reduced total number of leukocytes of the exudate that indicates excellent inhibition of prostaglandin production. Side effects of the compounds were examined on gastric mucosa, liver and stomach and none of the compounds showed significant side effects compared with reference nonsteroidal anti-inflammatory drugs (NSAIDs).

Administration, Oral↗
PubMed2002

Spiro[1,2,4-benzotriazine-3(4H),4'-(1'-substituted)piperidines] and related compounds as ligands for sigma receptors.

As analogues of some conformationally restricted spiropiperidine derivatives which are endowed with high affinity for sigma1 receptor, a set of 16 spiro[1,2,4-benzotriazine-3(4H),4'-(1'-substituted)piperidines] and congeneric compounds was prepared and tested for affinity to sigma1 receptor subtype. All N-arylalkyl substituted derivatives exhibited high affinity for the relevant receptor, with Ki in the low nanomolar range. Affinity for sigma2 subtype (assayed only for a few representative compounds) was from one to three order of magnitude lower. Spiro[1,2,4-benzotriazine-3(4H),4'-(1'-benzyl)piperidine] (2), with a ratio Ki sigma2/Ki sigma1 = 7000 should represent the most selective sigma1 ligand so far described.

Indicators and Reagents↗
PubMed1999

Synthesis, structural elucidation and pharmacological properties of some 5-acetyl-3,4-dihydro-6-methyl-4-(substituted phenyl)-2(1H) -pyrimidinones.

In this study, the synthesis of some new 5-acetyl-3,4-dihydro-6-methyl-4-(substituted phenyl)-2(1H)-pyrimidinones has been reported. The compounds were prepared by the Biginelli reaction of acetylacetone with aromatic aldehydes and urea. The structures of the compounds were characterized by UV, IR, 1H NMR, 13C NRM, mass spectra and elementary analysis. The calcium antagonistic activity of these compounds was tested in vitro on rat ileum precontracted with 4 x 10(-3) M barium chloride.

Animals↗