Supramolecular assemblies of hydrogen-bonded carboxylic acid dimers mediated by phenyl-pentafluorophenyl stacking interactions.
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Journal Article↗
Biomedical subjects
Maria J Milewska
Publications and source records attributed to Maria J Milewska.
Creation of hydrogen bonded 1D networks by co-crystallization of N,N'-bis(2-pyridyl)aryldiamines with dicarboxylic acids.
The preparation and crystal structures of fourteen complexes of N,N'-bis(2-pyridyl)aryldiamines with dicarboxylic acids and two complexes with squaric acid are reported. The recognition between the carboxylic acids and the 2-aminopyridine units occurs through the formation of the cyclic R(2)2 (8) hydrogen bond motif, whereas squaric acid creates the analogous R(2)2 (9) motif. In the 1:1 complexes the cyclic motifs generate infinite hydrogen-bonded 1D networks with the alternating component molecules. These networks are further organised into densely packed layers assembled through weaker C-H...O interactions. Analysis of the intermolecular interactions in these complexes led us to the synthesis of N,N'-bis(2-pyridyl)-2,2'-oxybis(aminobenzene) (5) which acts as a tritopic receptor of the carboxylic group and forms exclusively 2:1 complexes with dicarboxylic acids.
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Hydrophobic derivatives of 2-amino-2-deoxy-D-glucitol-6-phosphate: a new type of D-glucosamine-6-phosphate synthase inhibitors with antifungal action.
Several N-acyl and ester derivatives of 2-amino-2-deoxy-D-glucitol-6-phosphate (ADGP) have been synthesised and tested as inhibitors of fungal enzymes involved in early steps of chitin biosynthesis and for antifungal activity. All the tested derivatives were found to be much poorer inhibitors of the enzyme, D-glucosamine-6-phosphate (GlcN-6-P) synthase, than the parent compound but some of them exhibited much better antifungal activity. MIC values for the investigated compounds ranged between 10 mg mL(-1), found for ADGP and 0.3 mg mL(-1) for the most active derivative, namely ADGP dimethyl ester. Increased affinity of ADGP derivatives to the artificial immobilised cell membrane was correlated with their enhanced ability to be taken up by fungal cells by free diffusion. It was found that some of the examined derivatives behaved as 'pro-drugs' and after internalisation were converted into ADGP in the cell-free extract. This conversion was relatively rapid for ADGP esters but very slow for N-acyl derivatives. Results of our studies demonstrate a possibility of design and preparation of GlcN-6-P synthase inhibitors exhibiting antifungal activity.
Acylation↗
(S)-trans-cyclohexane-1,2-dicarboximide.
The molecule of the title compound, C(8)H(11)NO(2), contains a strained bicyclic system with a significantly twisted imide chromophore. The five-membered ring fragment containing the imide function is strongly puckered and adopts a half-chair conformation. The six-membered ring has a slightly distorted chair conformation. The molecules are joined by strong N-H.O and weak C-H.O hydrogen bonds into infinite chains.
Journal Article↗