Symmetric Bent-core Liquid Crystals of Some Schiff Bases Containing Azo Linkage

The paper presents the synthesis and liquid crystalline properties of some new symmetric bent-core liquid crystals containing a 1,3-dihydroxybenzene central core disubstituted with mesogenic units consisting of three aromatic rings connected through esteric, azomethinic and azo groups. The wings are ended with terminal acyloxy or alkyloxy chains containing 6 to 10 carbon atoms. Compounds were ob¬tained by the condensation reactions between some 4-((4-alcanoyloxyphenyl)azo)benzaldehydes or 4-((4-alkyloxyphenyl)azo)benzaldehydes with the 1,3-phenylene bis(4-aminobenzoate) core. The new synthe-sized compounds were characterized from structural point of view (1H NMR, 13C NMR, MS spectrosco¬py) and liquid crystalline properties (polarizing optical microscopy and differential scanning calorimetry). All the banana shaped compounds presented enantiotropic liquid crystalline properties, with a wide-ranging stability of mesophases both on heating and cooling cycles. The synthesized compounds present¬ed a good thermal stability in the existence range of the mesophases as evidenced by thermogravimetric studies. (doi: 10.5562/cca2150

Bent-Core Liquid Crystals: Structures and Mesomorphic Properties

Bent-core (BC) molecules became an attractive liquid crystal class due to their potential use in smart displays and photonic devices. In contrast to calamitic mesogens, bent-shaped mesogens are self-organized superstructures with remarkable properties, given the presence of polar order in mesophases, although the molecules themselves are not chiral. A particular interest represents the biaxial nematic liquid crystal materials that are used in display technology and allow a faster switching response, compared to calamitic liquid crystals, with considerably reduced costs. This chapter briefly reviews the bent-core liquid crystals with three different core units in the structure: (1) 2,5-disubstituted oxadiazole, (2) 1,3-disubstituted benzene, and (3) 2,7-disubstituted naphthalene. To the central bent units (BUs) containing reactive functional groups of phenolic or aminic type, various mesogenic groups are symmetrically or asymmetrically connected, via esterification or condensation reactions. The obtained compounds showed biaxial nematic and/or smectic mesophases with high transition temperatures in the case of oxadiazole derivatives or cholesteric and banana-type mesophases with lower transition temperatures in the case of benzene and naphthalene derivatives

Hybrid Pyridine Bis-Anthracene-Imidazolium Salt: NMR Studies on Zn-Acetate Complexation

We report here the design and synthesis of a new hybrid bis-anthracene-imidazolium salt, having a pyridine scaffold. NMR studies of dimer generation, as well as complexation with zinc acetate were performed

Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach

We report here an energy-efficient and straight synthesis of two new classes of derivatized fluorescent azatetracycles under ultrasound (US) irradiation. A first class of azatetracyclic compounds was synthesized by heterogeneous catalytic bromination of the α-keto substituent attached to the pyrrole moiety of the tetracyclic cycloadducts, while for the second, one class was synthesized by nucleophilic substitution of the bromide with the azide group. Comparative with conventional thermal heating (TH) under US irradiation, both types of reactions occur with substantially higher yields, shortened reaction time (from days to hours), lesser energy consumed, easier workup of the reaction, and smaller amounts of solvent required (at least three to five-fold less compared to TH), which make these reactions to be considered as energy efficient. The derivatized azatetracycle are blue emitters with λmax of fluorescence around 430–445 nm. A certain influence of the azatetracycle substituents concerning absorption and fluorescent properties was observed. Compounds anchored with a bulky azide group have shown decreased fluorescence intensity compared with corresponding bromides

Mesomorphic and Thermal Behavior of Symmetric Bent-Core Liquid Crystal Compounds Derived from Resorcinol and Isophthalic Acid

Bent-core liquid crystals (BCLC) have been widely studied as a result of their unusual polar and chiral properties. Similar to calamitic and discotic molecules, BCLC molecules also exhibit nematic phases, besides other higher order mesophases. The aim of this work is to comparatively analyze the mesomorphic behavior of some bent-core 1,3-disubstituted benzene core compounds derived from resorcinol and isophthalic acid. Thus, the two classes of compounds differ in the nature of the orientation of the ester bond between the benzene central core and the two branches attached to the core. The mesomorphic behavior was elucidated by polarized light optical microscopy and differential calorimetry. Given the relatively high isotropic points of the compounds, confirmation of the thermal stability in the domains manifesting liquid crystalline properties was performed by thermogravimetric studies. The theoretical explanation of the difference in mesomorphic behavior for the two classes was based on molecular modeling studies

Exploring Pyrrolo-Fused Heterocycles as Promising Anticancer Agents: An Integrated Synthetic, Biological, and Computational Approach

Five new series of pyrrolo-fused heterocycles were designed through a scaffold hybridization strategy as analogs of the well-known microtubule inhibitor phenstatin. Compounds were synthesized using the 1,3-dipolar cycloaddition of cycloimmonium N-ylides to ethyl propiolate as a key step. Selected compounds were then evaluated for anticancer activity and ability to inhibit tubulin polymerization in vitro. Notably, pyrrolo[1,2-a]quinoline 10a was active on most tested cell lines, performing better than control phenstatin in several cases, most notably on renal cancer cell line A498 (GI50 27 nM), while inhibiting tubulin polymerization in vitro. In addition, this compound was predicted to have a promising ADMET profile. The molecular details of the interaction between compound 10a and tubulin were investigated through in silico docking experiments, followed by molecular dynamics simulations and configurational entropy calculations. Of note, we found that some of the initially predicted interactions from docking experiments were not stable during molecular dynamics simulations, but that configurational entropy loss was similar in all three cases. Our results suggest that for compound 10a, docking experiments alone are not sufficient for the adequate description of interaction details in terms of target binding, which makes subsequent scaffold optimization more difficult and ultimately hinders drug design. Taken together, these results could help shape novel potent antiproliferative compounds with pyrrolo-fused heterocyclic cores, especially from an in silico methodological perspective

Cytotoxic substituted indolizines as new colchicine site tubulin polymerisation inhibitors

A potential microtubule destabilising series of new indolizine derivatives was synthesised and tested for their anticancer activity against a panel of 60 human cancer cell lines. Compounds 11a, 11b, 15a, and 15j showed a broad spectrum of growth inhibitory activity against cancer cell lines representing leukaemia, melanoma and cancer of lung, colon, central nervous system, ovary, kidney, breast, and prostate. Among them, compound 11a was distinguishable by its excellent cytostatic activity, showing GI50 values in the range of 10–100 nM on 43 cell lines. The less potent compounds 15a and 15j in terms of GI50 values showed a high cytotoxic effect against tested colon cancer, CNS cancer, renal cancer and melanoma cell lines and only on few cell lines from other types of cancer. In vitro assaying revealed tubulin polymerisation inhibition by all active compounds. Molecular docking showed good complementarity of active compounds with the colchicine binding site of tubulin