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Abstract A negative linear temperature expansion and a negative linear compressibility were observed for imidazolium benzoate salt. Its strongly anisotropic strain induced by the temperature and pressure changes has been explained by the mechanism of H-bonded helices deformed in the structure. X-ray diffraction and vibrational spectroscopy were used to analyze interactions in the crystal. The Quantum Theory of Atoms in Molecules (QTAiM) approach was applied to analyze the hydrogen bonds and other interactions. In the salt under study, the interactions within the helix are substantially higher in energy than between helices. With decreasing temperature and increasing pressure, the value of the helix pitch increases while the value of the semi-major axis decreases, which results in the negative linear expansion and negative linear compression, respectively.

A series of 2-(1H-indol-2-yl)-3-acrylonitrile derivatives, 2a–x, 3, 4a–b, 5a–d, 6a–b, and 7, were synthesized as potential antitumor and antimicrobial agents. The structures of the prepared compounds were evaluated based on elemental analysis, IR, 1H- and 13NMR, as well as MS spectra. X-ray crystal analysis of the representative 2-(1H-indol-2-yl)-3-acrylonitrile 2l showed that the acrylonitrile double bond was Z-configured. All compounds were screened at the National Cancer Institute (USA) for their activities against a panel of approximately 60 human tumor cell lines and the relationship between structure and in vitro antitumor activity is discussed. Compounds of interest 2l and 5a–d showed significant growth inhibition potency against various tumor cell lines with the mean midpoint GI50 values of all tests in the range of 0.38–7.91 μM. The prominent compound with remarkable activity (GI50 = 0.0244–5.06 μM) and high potency (TGI = 0.0866–0.938 μM) against some cell lines of leukemia (HL-60(TB)), non-small cell lung cancer (NCI-H522), colon cancer (COLO 205), CNS cancer (SF-539, SNB-75), ovarian cancer ((OVCAR-3), renal cancer (A498, RXF 393), and breast cancer (MDA-MB-468) was 3-[4-(dimethylamino)phenyl]-2-(1-methyl-1H-indol-2-yl)acrylonitrile (5c). Moreover, the selected 2-(1H-indol-2-yl)-3-acrylonitriles 2a–c and 2e–x were evaluated for their antibacterial and antifungal activities against Gram-positive and Gram-negative pathogens as well as Candida albicans. Among them, 2-(1H-indol-2-yl)-3-(1H-pyrrol-2-yl)acrylonitrile (2x) showed the most potent antimicrobial activity and therefore it can be considered as a lead structure for further development of antimicrobial agents. Finally, molecular docking studies as well as drug-likeness and ADME profile prediction were carried out.

Thiazolidine-2,4-dione core is widely used in the medicinal chemistry of different types of potential drug-like small molecules. In the present work, the synthesis of a novel non-condensed thiazolidine-2,4-dione-bearing derivative is reported by the two-step cost-effective approach including alkylation and Knoevenagel condensation. The structure of the synthesized 3-(2-diisopropylaminoethyl)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione was determined and characterized using 1H, 13C NMR, LC-MS spectra and the X-ray diffraction method.