Here, we have presented a new method of 1,1,3-triglycidyloxypropane (TGP) synthesis and investigated how cross-linker branching affects mechanical properties and cytotoxicity of chitosan scaffolds in comparison with those cross-linked using diglycidyl ethers of 1,4-butandiol (BDDGE) and poly(ethylene glycol) (PEGDGE). We have demonstrated that TGP is an efficient cross-linker for chitosan at a subzero temperature at TGP:chitosan molar ratios from 1:1 to 1:20. Although the elasticity of chitosan scaffolds increased in the following order of the cross-linkers PEGDGE > TGP > BDDGE, TGP provided cryogels with the highest compressive strength. Chitosan-TGP cryogels have shown low cytotoxicity for colorectal cancer HCT 116 cell line and supported the formation of 3D multicellular structures of the spherical shape and size up to 200 µm, while in more brittle chitosan-BDDGE cryogel this cell culture formed epithelia-like sheets. Hence, the selection of the cross-linker type and concentration for chitosan scaffold fabrication can be used to mimic the solid tumor microenvironment of certain human tissue, control matrix-driven changes in the morphology of cancer cell aggregates, and facilitate long-term experiments with 3D tumor cell cultures.

A preparative procedure has been developed for the synthesis of ethyl 3-oxo-2-(2,4,6-trinitrophenyl)­butanoate in an overall yield of 76% under mild conditions from commercially available picric acid and ethyl acetoacetate. The product structure was confirmed by X-ray analysis and ¹H NMR spectroscopy. The UV spectroscopic data revealed that the title compound is capable of intramolecular charge transfer.

A preparative method has been developed for the synthesis of 1,3,5-trinitro-2-(prop-2-yn-1-yloxy)benzene in 79% yield under mild conditions from commercially available initial compounds. The structure of the title compound has been confirmed by ¹ H NMR spectroscopy. 1,3,5-Trinitro-2-(prop-2-yn-1-yloxy)benzene has been found to form noncovalent bioconjugates with DNA molecules and deoxynucleoside triphosphates. The resulting bioconjugates can be involved in click reactions with azide dyes.

A preparative procedure has been developed for the synthesis of 3′-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 5′-phosphoramidite, the key reagent for the photolithographic synthesis of oligonucleotides on a solid support. The synthetic steps, including the preparation of 2-(2-nitrophenyl)propyl chloroformate, have been considered in detail, and conditions for the removal of the trityl protecting group from 3′-O-(2-(2-nitrophenyl)propoxycarbonyl)-5′-O-tritylthymidine have been optimized. The UV spectral properties of 3′-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 5′-phosphoramidite have been studied, its molar absorption coefficient has been refined, and the results have been compared with the previously reported data for 2-(2-nitrophenyl)propan-1-ol.

A procedure has been developed for the synthesis of 4-R-3-nitrophenyl carbonyl compounds via tandem oxidation–nitration of benzyl alcohols. The proposed one-pot procedure makes it possible to obtain the target products in good yields under mild conditions using stable commercially available reagents. The major requirement to the substrate structure is the presence of a mesomeric donor substituent at the para position with respect to the hydroxymethyl group.