ChemInform Abstract: 4,5‐DICARBAMYL‐2‐ARYLOXAZOLES. SYNTHESIS AND ANTI‐INFLAMMATORY PROPERTIES

Tarzia, Giorgio; Schiatti, P; D, Selva; Favara, D.; Ceriani, Sergio

doi:10.1002/chin.197642260

Cited by 2 publications

(5 citation statements)

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“…Synthesis of N-imidoylimidate 9. Ethyl 4-methoxybenzimidate hydrochloride 29 (5.6 g, 30.0 mmol, 1.0 equiv.) was suspended in dry dichloromethane (20 mL) and triethylamine (2.8 mL, 20.0 mmol, 2.0 equiv.)…”

Section: General Proceduresmentioning

confidence: 99%

Fluorescent benzene-centered mono-, bis- and tris-triazapentadiene–boron complexes

et al. 2015

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A series of novel benzene centered mono-, bis-and tris-1,3,5-triazapentadiene ligands 6a-e was synthesized and investigated with respect to their reactivity towards triphenylborane. The resulting blue-fluorescent boron complexes 14a-e with a six-membered ring chelate structure show excellent thermal and chemical stability. All title compounds were completely characterized including X-ray diffraction studies for 14a-c and 14e. Whereas the absorption spectra of all three classes of compounds are similar, the fluorescence spectra show distinct differences. Thus, the emission spectra of 14a,b show Stokes shifts of 4100-6700 cm −1 with low quantum yields both in solution and in the solid state. However, the more bulky compounds 14c-e show markedly larger molar extinction coefficients and smaller bathochromic shifts compared to 14a,b. For all compounds, we observe significantly more intense red-shifted fluorescence in the solid state compared to that in dichloromethane solutions. For the interpretation of the absorption properties TD-DFT studies were performed based on DFT geometry optimizations.

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Section: General Proceduresmentioning

confidence: 99%

Fluorescent benzene-centered mono-, bis- and tris-triazapentadiene–boron complexes

et al. 2015

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“…The resultant precipitate was filtered, washed with H 2O, and dried in a vacuum oven overnight to give 15.2 g (77%) of the title compound as a white solid. 1 (39). A mixture of 6-phenyl-1H-pyrrolo [3,2-d]pyrimidine-2,4-diol (38) (6.0 g, 26.6 mmol) and POCl3 (210 mL, 229 mmol) in a 500-mL, round-bottomed flask was heated at 120°C for 60 h. POCl3 was removed in vacuo to give a dark-red residue.…”

Section: -Amino-6-phenylpyrrolo[32-d]pyrimidin-4-ol (29) To a Rounmentioning

confidence: 99%

“…Treatment of ethyl acetoacetate ( 9 ) with sodium nitrite and acetic acid provided ethyl 2-hydroxyimino-3-butyrate ( 10 ). , This material was reduced with zinc and sulfuric acid to give the corresponding 2-aminoacetoacetic acid ethyl ester . This amine was isolated and acylated with an appropriate acid chloride to give 11 ; however, higher yields were obtained by the in situ acylation of the amine by the method described by Tarzia and co-workers . Condensation of the ethyl N -acylated-2-aminoacetoacetates 11 with acetamidine hydrochloride in sodium ethoxide provided acylpyrimidine intermediates 12 .…”

Section: Chemistrymentioning

confidence: 99%

“…37 This amine was isolated and acylated with an appropriate acid chloride to give 11; 38 however, higher yields were obtained by the in situ acylation of the amine by the method described by Tarzia and co-workers. 39 Condensation of the ethyl N-acylated-2-aminoacetoacetates 11 with acetamidine hydrochloride in sodium ethoxide provided acylpyrimidine intermediates 12. Madelung cyclization of pyrimidines 12 at 360 °C gave the desired 3-hydroxypyrrolo [3,2-d]pyrimidines 13, albeit in poor yields.…”

Section: Chemistrymentioning

confidence: 99%

“…2,4-Dichloro-6-phenylpyrrolo[3,2-d]pyrimidine (39). A mixture of 6-phenyl-1H-pyrrolo [3,2-d]pyrimidine-2,4-diol (38) (6.0 g, 26.6 mmol) and POCl3 (210 mL, 229 mmol) in a 500-mL, round-bottomed flask was heated at 120 °C for 60 h. POCl3 was removed in vacuo to give a dark-red residue.…”

Section: Phenyl-n-(6-phenyl-4-piperidylpyrrolo[32-d]pyrimidin-2-yl)fo...mentioning

confidence: 99%

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Structure−Activity Relationships of a Series of Pyrrolo[3,2-d]pyrimidine Derivatives and Related Compounds as Neuropeptide Y5 Receptor Antagonists

Norman

Chen

et al. 2000

J. Med. Chem.

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Neuropeptide Y (NPY) has been shown to play an important role in the regulation of food intake and energy balance. Pharmacological data suggests that the Y5 receptor subtype contributes to the effects of NPY on appetite, and therefore a Y5 antagonist might be a useful therapeutic agent for the treatment of obesity. In attempts to identify potential Y5 antagonists, a series of pyrrolo[3, 2-d]pyrimidine derivatives was prepared and evaluated for their ability to bind to Y5 receptors in vitro. We report here the synthesis and initial structure-activity relationship investigations for this class of compounds. The target compounds were prepared by a variety of synthetic routes designed to modify both the substitution and the heterocyclic core of the pyrrolo[3,2-d]pyrimidine lead 1. In addition to identifying several potent Y5 antagonists for evaluation as potential antiobesity agents, a pharmacophore model for the human Y5 receptor is presented.

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ChemInform Abstract: 4,5‐DICARBAMYL‐2‐ARYLOXAZOLES. SYNTHESIS AND ANTI‐INFLAMMATORY PROPERTIES

Abstract: Ausgehend von den Verbindungen (I), (VIII) bzw. (XIV) werden nach den aufgezeichneten Reaktionsfolgen die Oxazolylcarbonsäureamide (VII), (XIII) bzw. (XVI) synthetisiert und pharmakologisch untersucht.

Cited by 2 publications

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Fluorescent benzene-centered mono-, bis- and tris-triazapentadiene–boron complexes

Fluorescent benzene-centered mono-, bis- and tris-triazapentadiene–boron complexes

Structure−Activity Relationships of a Series of Pyrrolo[3,2-d]pyrimidine Derivatives and Related Compounds as Neuropeptide Y5 Receptor Antagonists

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