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According to the recent studies bezylcarboxamide fragment attached to the thiophene ring of thieno[2,3-d]pyrimidine is beneficial for antimicrobial activity of the compounds. Therefore we focused our efforts on constructing of the simple molecules such as N-(benzyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamides to get deeper insight into their antimicrobial activity. As the optimal procedure for preparation of target compounds we choose 1,1'-carbonyldiimidazole promoted interaction of 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid with the series of substituted benzyl amines. The obtained amides showed good activity against the strains of S. aureus and B. subtilis, which was higher for the derivative without substituents in benzene ring or the compounds with small substituents like methyl or methoxyl groups in the para-position of the benzene ring. Docking studies showed that despite the good values of the scoring functions, the conformational analysis of the ligands' poses in the active site revealed their ability for only partial inhibition of TrmD of P. aeruginosa. [ABSTRACT FROM AUTHOR]

The phenolic compounds in the leaves of 12 species of birch trees of the subgenera Neurobetula, Betulenta, and Betula were biochemically profiled using HPTLC. The duration of the vegetation period was found to be significantly related to the content of total phenols (r = 0.74) and flavonoids in leaves (r = 0.65). The correlations for Neurobetula plants were 0.86 and 0.91, respectively. The relationship between the duration of the growing season and the concentration of phenolic compounds in Betula plants was inverse (r = −0.84). A cluster analysis of phytochemical profiles revealed that the studied birch species form groups that coincide with the subgenera proposed by De Jong due to an affinity with the qualitative composition of phenolic compounds. A multiple correlation analysis confirmed the relationship between the qualitative composition of phenolic compounds and the morphological characteristics of the leaves. The results of phytochemical profiling revealed that the qualitative composition of polyphenols in the leaves of 12 birch species is quite specific, allowing the use of individual compounds as additional differential biochemical characters in identifying species and hybrids and studying their potential role in plant adaptation to habitat conditions. [ABSTRACT FROM AUTHOR]

6-Heteryl-5-methylthieno[2,3-d]pyrimidin-2,4(1H,3H)-diones are of great interest as the promising objects for the search of antibacterials. In this communication, we obtained 6-(imidazo[1,2-a]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione by interaction of 6-(bromoacetyl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione with 2-aminopyridine. The obtained heterocyclic hybrid was further modified by alkylation with 2-chloroarylacetamides. Antimicrobial activity studies for the synthesized compounds using the agar well diffusion method revealed their moderate activity against S. aureus, E. coli and B. subtilis. According to the double dilution assay MIC value results for 6-(imidazo[1,2-a]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneagainst P. aeruginosa was less than the value determined for the reference drug streptomycin. The docking study of the synthesized compounds to the active site of TrmD isolated from P. aeruginosa did not show their effective inhibitory activity. [ABSTRACT FROM AUTHOR]

Photoisomerizable peptides are promising drug candidates in photopharmacology. While azobenzene- and diarylethene-containing photoisomerizable peptides have already demonstrated their potential in this regard, reports on the use of spiropyrans to photoregulate bioactive peptides are still scarce. This work focuses on the design and synthesis of a spiropyran-derived amino acid, (S)-2-amino-3-(6'-methoxy-1',3',3'-trimethylspiro-[2H-1-benzopyran-2,2'-indolin-6-yl])propanoic acid, which is suitable for the preparation of photoisomerizable peptides. The utility of this amino acid is demonstrated by incorporating it into the backbone of BP100, a known membrane-active peptide, and by examining the photoregulation of the membrane perturbation by the spiropyran-containing peptides. The toxicity of the peptides (against the plant cell line BY-2), their bacteriotoxicity (E. coli), and actin-auxin oscillator modulation ability were shown to be significantly dependent on the photoisomeric state of the spiropyran unit., (© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)