Design, synthesis and evaluation of novel sulfonamides as potential anticancer agents

Kachaeva, Maryna; Hodyna, Diana; Semenyuta, Ivan; Pilyo, Stepan; Прокопенко, В. М.; Kovalishyn, Vasyl; Metelytsia, Larysa; Броварец, В. С.

doi:10.1016/j.compbiolchem.2018.04.006

Cited by 48 publications

(31 citation statements)

References 27 publications

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“…4‐Cyano‐1,3‐oxazole‐5‐sulfonyl amides 19 ‐ 22 have been synthesized according to the procedure from sulfonyl chlorides 17 or 18 by refluxing with appropriate amine and excess of triethylamine (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…To understand the connection between the chemical constitution of the 1,3‐oxazole derivatives and their biological activity, particularly, as potential anticancer agents, the detailed study of the qualitative structure‐activity relationship (QSAR) of the some substituted 2‐phenyl‐1,3‐oxazoles were early performed . It was a modeled formation of complex in the binding site of tubulin, and it showed the effective protein‐ligand interaction.…”

Section: Resultsmentioning

confidence: 99%

“…The latter were converted into the corresponding sulfonyl derivatives 12-16 by oxidation with hydrogen peroxide. [46] 4-Cyano-1,3-oxazole-5-sulfonyl amides 19-22 have been synthesized according to the procedure [35] from sulfonyl chlorides 17 or 18 [47] by refluxing with appropriate amine and excess of triethylamine (Scheme 2).…”

Section: Chemistrymentioning

confidence: 99%

“…To understand the connection between the chemical constitution of the 1,3-oxazole derivatives and their biological activity, particularly, as potential anticancer agents, the detailed study of the qualitative structure-activity relationship (QSAR) of the some substituted 2-phenyl-1,3-oxazoles were early performed. [2,35] It was a modeled formation of complex in the binding site of tubulin, and it showed the effective protein-ligand interaction. So, the results of molecular docking have indicated the formation of the π-σ interaction between the conjugated systems of the 1,3-oxazole ligand and peptide fragment (σ is lone electron pair at nitrogen atom), which stabilizes the protein-ligand complex; the predicted binding affinity ≈ −7.7 kcal/mol.…”

Section: Quantum-chemical Modeling Of Donor/acceptor Property Of Sumentioning

confidence: 99%

“…[5,6] Thus, 1,3-oxazole could be considered as perspective moiety in the design and further synthesis of novel biologically active agents that exert anticancer activity. [1][2][3][4][23][24][25][26][27][28][29][30][31][32][33][34] So, the QSAR models were developed for wide site of 1,3-oxazole derivatives showing inhibitory effect on the NCI-60 cancer cell lines, [2,35] and the well correlation was established between many descriptors and biological activity. So, it was investigated the interaction of the azole derivatives with the tubulin inhibitors which significantly improve the clinical effectivity of novel proposed biological active molecules as anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

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Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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A series of new 1,3‐oxazole derivatives, containing in position 5 both donor and acceptor substituents were synthesized. These substances were considered as potentially active anticancer pharmacophores in the human tumor cell line panel derived from nine cancer types, including lung, colon, melanoma, renal, ovarian, brain, leukemia, breast, and prostate. Primary in vitro one‐dose anticancer screening was shown that compounds with acceptor substituents (such as –C(O)OMe, –CN) in the position 5 inhibit the growth of most cell lines, and compounds with donor substituents (such as –NHR, −SR) in the position 5 do not practically inhibit the growth of cancer cell lines. It can be assumed that the pharmacological activity of 1,3‐oxazole derivatives depends on donor/acceptor nature of the substituents in position 5. It was proposed to evaluate the donor/acceptor ability of 1,3‐oxazole derivatives using the special parameter φ0, which takes into account the relative position of the boundary levels (HOMO end LUMO). The quantum‐chemical modeling was performed; the special parameter φ0 for 1,3‐oxazole derivatives correlates with the experimental results. Quantum‐chemical calculations of the special parameter φ0 allow modeling the pharmacological activity of 1,3‐oxazole derivatives by introducing donor or acceptor substituents at position 2 or 5. This work may be useful for chemists to develop a target synthesis of potential biologically active compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Quantum-chemical Modeling Of Donor/acceptor Property Of Sumentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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Significance of Selective Protein Degradation in the Development of Novel Targeted Drugs and Its Implications in Cancer Therapy

Yang

Wang

Feng

et al. 2020

Advanced Therapeutics

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The evolution of traditional chemotherapeutic drugs to targeted drugs has led to major changes in cancer treatment. However, it remains difficult to develop effective targeted drugs that can act against “undruggable” proteins, including some well‐known oncoproteins such as KRas. Moreover, mutations of target genes limit the use of targeted drugs. Although some strategies such as RNA interference and DNA editing have been adopted to solve these problems, their clinical use remains challenging. Therefore, new strategies are urgently needed to meet the dilemmas encountered in the use of targeted drugs. As protein degradation is a rapid and well‐regulated biological process in cells, targeting protein degradation by inducing cellular protein degradation machinery, regardless of the status of the target, is an attractive idea for developing novel targeted drugs. This review summarizes recent advances in targeted protein degradation, with a focus on the current reagents and strategies used for inducing selective degradation of target proteins to provide clues for the development of novel anticancer drugs and cancer therapies.

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An overview of sulfonamide‐based conjugates: Recent advances for tuberculosis treatment

Scarim

Pavan

2022

Drug Development Research

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In 2019, tuberculosis (TB) caused approximately 1.4 million deaths around the world.TB is an infectious respiratory disease mainly caused by Mycobacterium tuberculosis.The lack of new drugs to treat drug-resistant strains is a principal factor for the continuous slow rise in TB infections. Sulfonamides are active moieties in various drugs used against several sicknesses, including TB. Our aim is to aid the development of new TB treatments and drugs by describing recent improvements (2011-2021) to sulfonamide-based compounds.

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Design, synthesis and evaluation of novel sulfonamides as potential anticancer agents

Cited by 48 publications

References 27 publications

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Significance of Selective Protein Degradation in the Development of Novel Targeted Drugs and Its Implications in Cancer Therapy

An overview of sulfonamide‐based conjugates: Recent advances for tuberculosis treatment

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