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Design, Synthesis and Biological Applications of Functional Compounds and Materials

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Materials Science".

Deadline for manuscript submissions: closed (20 January 2025) | Viewed by 6710

Special Issue Editor


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Guest Editor
Institute of Chemistry, Saint Petersburg State University, 198504 Peterhof, Russia
Interests: heterocyclic compounds; lactams; multicomponent reactions; imines; anhydrides; diazo compounds

Special Issue Information

Dear Colleagues,

We are pleased to present a Special Issue of the International Journal of Molecular Science, entitled “Design, Synthesis and Biological Applications of Functional Compounds and Materials”.

This Special Issue will primarily focus on the rational design and synthesis of the organic functional compounds and materials employed in the biological applications and will include (but are not limited to) discussions of drug development, administration and delivery, personalized healthcare and the monitoring of the parameters of biological objects and living bodies.

The modern toolbox of synthetic chemistry provides extremely broad chemical diversity, and rational design plays an extremely vital role in the development of functional compounds and materials, increasing the win rate of the targeted synthesis. Approaches to the targeted synthesis of biological and other applications are also essential for the development of the functional compounds and materials.

In this Special Issue, we welcome the studies devoted to the design of functional compounds and materials andsynthetic approaches for the preparation of various classes, families and scaffolds of such materials. We are also interested in structure–property studies, examinations of biological activity and research into other functional applications of organic compounds and materials.

Suitable topics include, but are not limited to:

  • Rational design and synthesis of functional compounds and materials;
  • Synthesis of biologically active compounds and materials;
  • Structure–property relationship;
  • In silico screening for the functional properties.

Dr. Olga Yu Bakulina
Guest Editor

Manuscript Submission Information

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Keywords

  • rational design
  • organic synthesis
  • targeted synthesis
  • functional compounds
  • biological activity
  • medicinal chemistry
  • drug developement

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Published Papers (3 papers)

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Research

25 pages, 2653 KiB  
Article
1,3-Dipolar Cycloaddition of Nitrile Oxides and Nitrilimines to (−)-β-Caryophyllene: Stereoselective Synthesis of Polycyclic Derivatives and Their Biological Testing
by Dmitry E. Shybanov, Maxim E. Kukushkin, Yuri K. Grishin, Vitaly A. Roznyatovsky, Viktor A. Tafeenko, Louay Abo Qoura, Vadim S. Pokrovsky, Olga I. Yarovaya, Svetlana V. Belyaevskaya, Alexandrina S. Volobueva, Iana L. Esaulkova, Vladimir V. Zarubaev and Elena K. Beloglazkina
Int. J. Mol. Sci. 2024, 25(21), 11435; https://doi.org/10.3390/ijms252111435 - 24 Oct 2024
Cited by 2 | Viewed by 2203
Abstract
The cycloaddition of nitrile oxides and nitrilimines to one or both of the C=C double bonds of caryophyllene is described. The possibility of introducing five-membered fused and spiro-linked heterocycles into the structure of sesquiterpenes by the 1,3-dipolar cycloaddition reactions of nitrile oxides and [...] Read more.
The cycloaddition of nitrile oxides and nitrilimines to one or both of the C=C double bonds of caryophyllene is described. The possibility of introducing five-membered fused and spiro-linked heterocycles into the structure of sesquiterpenes by the 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrilimines to caryophyllene was demonstrated. As a result of these reactions, pharmacophore fragments of isoxazoline and pyrazoline are introduced into the structure of caryophyllene, which leads to an increase in the conformational rigidity of the molecule. A complete stereochemical assignment of 1,3-dipolar cycloaddition adducts to caryophyllene was carried out. The study of antiviral and cytotoxic activity for some heterocyclic derivatives synthesized in this work revealed relatively high biological activity of previously little-studied cycloaddition adducts at the exocyclic C=CH2 bond of caryophyllene. The effect of substituents in the synthesized heterocycles on biological activity was demonstrated. Compounds with a good inhibitory effect on the H1N1 influenza virus were revealed. The activity of the compound was demonstrated up to 6 h post infection, and this could be due to slight inhibiting activity against viral neuraminidase, necessary at the stage of progeny virion budding. Full article
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20 pages, 5088 KiB  
Article
Discovery of Indole–Thiourea Derivatives as Tyrosinase Inhibitors: Synthesis, Biological Evaluation, Kinetic Studies, and In Silico Analysis
by Yang Xu, Xuhui Liang and Chang-Gu Hyun
Int. J. Mol. Sci. 2024, 25(17), 9636; https://doi.org/10.3390/ijms25179636 - 5 Sep 2024
Cited by 4 | Viewed by 2546
Abstract
Tyrosinase, a key enzyme in melanin synthesis, represents a crucial therapeutic target for hyperpigmentation disorders due to excessive melanin production. This study aimed to design and evaluate a series of indole–thiourea derivatives by conjugating thiosemicarbazones with strong tyrosinase inhibitory activity to indole. Among [...] Read more.
Tyrosinase, a key enzyme in melanin synthesis, represents a crucial therapeutic target for hyperpigmentation disorders due to excessive melanin production. This study aimed to design and evaluate a series of indole–thiourea derivatives by conjugating thiosemicarbazones with strong tyrosinase inhibitory activity to indole. Among these derivatives, compound 4b demonstrated tyrosinase inhibitory activity with an IC50 of 5.9 ± 2.47 μM, outperforming kojic acid (IC50 = 16.4 ± 3.53 μM). Kinetic studies using Lineweaver–Burk plots confirmed competitive inhibition by compound 4b. Its favorable ADMET and drug-likeness properties make compound 4b a promising therapeutic candidate with a reduced risk of toxicity. Molecular docking revealed that the compounds bind strongly to mushroom tyrosinase (mTYR) and human tyrosinase-related protein 1 (TYRP1), with compound 4b showing superior binding energies of −7.0 kcal/mol (mTYR) and −6.5 kcal/mol (TYRP1), surpassing both kojic acid and tropolone. Molecular dynamics simulations demonstrated the stability of the mTYR−4b complex with low RMSD and RMSF and consistent Rg and SASA values. Persistent strong hydrogen bonds with mTYR, along with favorable Gibbs free energy and MM/PBSA calculations (−19.37 kcal/mol), further support stable protein–ligand interactions. Overall, compound 4b demonstrated strong tyrosinase inhibition and favorable pharmacokinetics, highlighting its potential for treating pigmentary disorders. Full article
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29 pages, 14737 KiB  
Article
New Amphiphilic Terpolymers of N-Vinylpyrrolidone with Acrylic Acid and Triethylene Glycol Dimethacrylate as Promising Drug Delivery: Design, Synthesis and Biological Properties In Vitro
by Svetlana V. Kurmaz, Roman I. Komendant, Evgenia O. Perepelitsina, Vladimir A. Kurmaz, Igor I. Khodos, Nina S. Emelyanova, Natalia V. Filatova, Vera I. Amozova, Anastasia A. Balakina and Alexey A. Terentyev
Int. J. Mol. Sci. 2024, 25(15), 8422; https://doi.org/10.3390/ijms25158422 - 1 Aug 2024
Cited by 3 | Viewed by 1339
Abstract
The terpolymers of N-vinylpyrrolidone (VP) with acrylic acid and triethylene glycol methacrylate were synthesized with more than 90% yield by radical copolymerization in ethanol from monomeric mixtures of different molar composition (98:2:2, 95:5: 2 and 98:2:5) and their monomer composition, absolute molecular masses [...] Read more.
The terpolymers of N-vinylpyrrolidone (VP) with acrylic acid and triethylene glycol methacrylate were synthesized with more than 90% yield by radical copolymerization in ethanol from monomeric mixtures of different molar composition (98:2:2, 95:5: 2 and 98:2:5) and their monomer composition, absolute molecular masses and hydrodynamic radii in aqueous media were determined. Using the MTT test, these terpolymers were established to be low toxic for non-tumor Vero cells and HeLa tumor cells. Polymer compositions of hydrophobic dye methyl pheophorbide a (MPP) based on studied terpolymers and linear polyvinylpyrrolidone (PVP) were obtained and characterized in water solution. Quantum-chemical modeling of the MPP-copolymer structures was conducted, and the possibility of hydrogen bond formation between terpolymer units and the MPP molecule was shown. Using fluorescence microscopy, the accumulation and distribution of polymer particles in non-tumor (FetMSC) and tumor (HeLa) cells was studied, and an increase in the accumulation of MPP with both types of particles was found. Full article
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