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PubMed · 14097621

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B VURDELJA. 1963. [WITHOUT ANALEPTICS?].. https://pubmed.ncbi.nlm.nih.gov/14097621/

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Supramolecular chirality of the hydrogen-bonded complex Langmuir-Blodgett film of achiral barbituric acid and melamine.

Complex monolayers of barbituric acid and melamine were formed by spreading a chloroform solution of amphiphilic barbituric acid on the subphase of melamine solution. It was confirmed that the complex monolayer was formed through in situ complementary hydrogen bonding at the air-water interface. It was interesting to find that the complex LB films showed supramolecular chirality although both of the molecules were achiral, as verified by the circular dichroism spectral measurements. It was suggested that the pi-pi stacking of the neighboring barbituric acid and melamine group in a helical sense resulted in the chirality of the molecular assemblies. Due to the directionality of the hydrogen bonding, the BA-M film could form regular aligned nanofibers on the AFM images. Increasing the subphase temperature will lead to the decrease of CD intensity and the change of the morphologies. We suggested that the strength of the hydrogen bonding resulted in the difference.

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C-5-disubstituted barbiturates as potential molecular probes for noninvasive matrix metalloproteinase imaging.

Studies have demonstrated a positive correlation between inflammation, metastasis, or atherosclerosis and the unbalanced or culminated expression of matrix metalloproteinases (MMPs). The molecular imaging of locally upregulated MMP activity in vivo is a clinical challenge. Actually, radioligands based on nonpeptidyl MMP inhibitors (MMPIs) are currently in development as putative radiopharmaceutical agents for the noninvasive in vivo assessment of activated MMPs. Nonpeptidyl MMPIs bind to the zinc active site of the activated enzyme via mono- (e.g. carboxylate) or bidentate (e.g. hydroxamate) complexation thereby exhibiting a broad-spectrum MMP binding potency. Thus, these mentioned endopeptidase inhibitors should be useable lead compounds for the redevelopment as diagnostic MMPI radiotracers. Recently, the non-hydroxamate C-5-disubstituted pyrimidine-2,4,6-triones were disclosed as subgroup-selective MMP inhibitors. We here describe a set of fine-tuned barbiturates as a new class of MMPI radiotracers for the noninvasive in vivo visualization of activated MMPs using scintigraphic techniques such as SPECT or PET.

Barbiturates↗

5-Butyl-5-ethylbarbituric acid: a phase transition at low temperature.

The room-temperature crystal structure of 5-butyl-5-ethylbarbituric acid (generally known as butobarbitone), C10H16N2O3, was reported in space group C2/c [Bideau (1971). C. R. Acad. Sci. Paris Ser. C, 272, 757-760]. A redetermination at 120 K using synchrotron radiation shows the space group at this temperature to be P2(1)/n and not C2/c. There are two crystallographically independent molecules in the asymmetric unit, but no solvent. Reported issues concerning possible disorder of the molecule are addressed; the butyl substituent of one of the molecules adopts an unusual conformation in being not fully extended. A subsequent re-collection at room temperature shows that the space group is indeed C2/c (A2/a with the axes selected in this report), and so the crystal structure undergoes a phase change upon cooling to 120 K.

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