Stanisław Leśniak

Optically pure hetero-organic organocatalysts, bearing a hydroxy moiety, a stereogenic sulfinyl group and a chiral amine moiety, have revealed high catalytic activity in the asymmetric reduction of various N-aryl ketimines leading to the corresponding chiral amines. Desired products were formed in high chemical yields (up to 95%) and with ee’s up to 97%. The influence of particular stereogenic centres on the stereochemical outcome of the reduction reaction is discussed.

In the present paper, we report the synthesis and evaluation of in vitro antimicrobial activities of aziridine-thiourea derivatives. A series of aziridines in reaction with isocyanates and isothiocyanates to obtain urea and thiourea derivatives were used. The structures of all new products were confirmed based on spectroscopic data (¹H-NMR, ¹³C-NMR, HR-MS). These compounds were screened for their in vitro antimicrobial activity against a panel of Gram-positive and Gram-negative strains of bacteria. Six of the tested compounds appeared to be promising agents against reference strains of Escherichia coli, Staphylococcus aureus and Staphylococcus epidermidis. Subsequently, compounds exhibiting promising antibacterial activity were tested against twelve clinical isolates of S. aureus from three different sources of infection. The most bactericidal compounds (MIC = 16–32 µg/mL) showed better antibacterial activity against MRSA than ampicillin and streptomycin. The in vitro cytotoxicity analysis on L929 murine fibroblast and HeLa human tumor cell line using the MTT assay allowed us to select the least toxic compounds for future investigation.

Optically pure, diastereomeric aziridine amides built on the chiral skeletons of camphor, fenchone, and menthone have proven to be highly efficient ligands for enantioselective asymmetric direct aldol reaction in the presence of water and zinc triflate. Desired products were formed in moderate to high chemical yields (up to 95%) and with enantiomeric excess up to 99%. The influence of the stereogenic centers located at the aziridine subunit on the stereochemical course of the reaction is discussed.

Herein, an advantage of the use of IDSCRF- over UFF-radii-based solute cavities in GIAO/DFT calculations is presented for the ¹³C and especially ¹⁵N NMR chemical shifts made for several bicyclic aromatic nitrogen heterocycles in CDCl₃ solution treated within the classical IEF-PCM solvation scheme. Successful application of the IDSCRF-radii in the non 1:1 joint multinuclear ¹H/¹³C and particularly ¹H/¹³C/¹⁵N correlations of the measured δ_H,C(,N) values to those obtained theoretically is also documented for a series of test systems (−268 ≤ δ_N ≤ −72 ppm). The experimentally yet unknown δ_N’s were found in this way for the title compounds via a trinuclear eq 1 determined for an optimally chosen value of the multiplication factor of initial raw δ_H data (m_H = 10). Such a simultaneous analysis of the δ_H,C(,N) data is proposed as a novel method to study the solution structure of the other similar conformationally homogeneous (bio)organic compounds. The issue of small spurious imaginary vibrational frequencies computed for a few molecular systems using the Gaussian 09 default UFF-radii is briefly considered as well.