Antitumor activity of 3,4-ethylenedioxythiophene derivatives and quantitative structure-activity relationship analysis

Jukić, Marijana; Rastija, Vesna; Opačak-Bernardi, Teuta; Stolić, Ivana; Krstulović, Luka; Bajić, Miroslav; Glavaš‐Obrovac, Ljubica

doi:10.1016/j.molstruc.2016.11.074

Cited by 12 publications

(3 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Substitution of two OH groups in compound 12 at the position 2,4 decreased values of Mor22u (0.216) and antioxidant activity (log %DPPH = 0.924). Our recent study has also evinced sensitivity of the 3D-MoRSE descriptor Mor19e to the changes of substituents and their position on the 3,4-ethylenedioxythiophene central unit [ 40 ].…”

Section: Resultsmentioning

confidence: 99%

Deep Eutectic Solvents as Convenient Media for Synthesis of Novel Coumarinyl Schiff Bases and Their QSAR Studies

et al. 2017

Self Cite

View full text Add to dashboard Cite

Deep eutectic solvents, as green and environmentally friendly media, were utilized in the synthesis of novel coumarinyl Schiff bases. Novel derivatives were synthesized from 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide and corresponding aldehyde in choline chloride:malonic acid (1:1) based deep eutectic solvent. In these reactions, deep eutectic solvent acted as a solvent and catalyst as well. Novel Schiff bases were synthesized in high yields (65–75%) with no need for further purification, and their structures were confirmed by mass spectra, 1H and 13C NMR. Furthermore, their antioxidant activity was determined and compared to antioxidant activity of previously synthesized derivatives, thus investigating their structure–activity relationship utilizing quantitative structure-activity relationship QSAR studies. Calculation of molecular descriptors has been performed by DRAGON software. The best QSAR model (Rtr = 0.636; Rext = 0.709) obtained with three descriptors (MATS3m, Mor22u, Hy) implies that the pairs of atoms higher mass at the path length 3, three-dimensional arrangement of atoms at scattering parameter s = 21 Å−1, and higher number of hydrophilic groups (-OH, -NH) enhanced antioxidant activity. Electrostatic potential surface of the most active compounds showed possible regions for donation of electrons to 1,1-diphenyl-2-picryhydrazyl (DPPH) radicals.

show abstract

Section: Resultsmentioning

confidence: 99%

Deep Eutectic Solvents as Convenient Media for Synthesis of Novel Coumarinyl Schiff Bases and Their QSAR Studies

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…For anticancer drug development, designing molecules that can selectively inhibit the proliferation of abnormal cells with minimal or no effect on normal cells is critical. Therefore, developing anticancer drugs is of utmost importance worldwide [1,2,3].…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Benzimidazole-Chalcone Derivatives as Potential Anticancer Agents

Hsieh

Chang

et al. 2019

Molecules

View full text Add to dashboard Cite

Numerous reports have shown that conjugated benzimidazole derivatives possess various kinds of biological activities, including anticancer properties. In this report, we designed and synthesized 24 new molecules comprising a benzimidazole ring, arene, and alkyl chain-bearing cyclic moieties. The results showed that the N-substituted benzimidazole derivatives bearing an alkyl chain and a nitrogen-containing 5- or 6-membered ring enhanced the cytotoxic effects on human breast adenocarcinoma (MCF-7) and human ovarian carcinoma (OVCAR-3) cell lines. Among the 24 synthesized compounds, (2E)-1-(1-(3-morpholinopropyl)-1H-benzimidazol-2 -yl)-3-phenyl-2-propen-1-one) (23a) reduced the proliferation of MCF-7 and OVCAR-3 cell lines demonstrating superior outcomes to those of cisplatin.

show abstract

“…Consonni and co-workers [ 6 ] proposed a new molecular representation calculated from the spatial coordinates of the molecule atoms in a chosen conformation, allowing for a more accurate similarity/diversity analysis of compounds stored in databases. The development of structure–activity modeling of different biological/physicochemical endpoints confirmed the usefulness of GETAWAY descriptors in molecular sciences [ 8 , 9 , 10 , 11 , 12 , 13 , 14 ]. Several studies prove that the combination of GETAWAY and WHIM descriptors significantly improves the predictive power of the QSAR model [ 15 , 16 , 17 , 18 ].…”

Section: Introductionmentioning

confidence: 84%

HATS5m as an Example of GETAWAY Molecular Descriptor in Assessing the Similarity/Diversity of the Structural Features of 4-Thiazolidinone

Zapadka

Dekowski²,

Kupcewicz

2022

IJMS

View full text Add to dashboard Cite

Among the various methods for drug design, the approach using molecular descriptors for quantitative structure–activity relationships (QSAR) bears promise for the prediction of innovative molecular structures with bespoke pharmacological activity. Despite the growing number of successful potential applications, the QSAR models often remain hard to interpret. The difficulty arises from the use of advanced chemometric or machine learning methods on the one hand, and the complexity of molecular descriptors on the other hand. Thus, there is a need to interpret molecular descriptors for identifying the features of molecules crucial for desirable activity. For example, the development of structure–activity modeling of different molecule endpoints confirmed the usefulness of H-GETAWAY (H-GEometry, Topology, and Atom-Weights AssemblY) descriptors in molecular sciences. However, compared with other 3D molecular descriptors, H-GETAWAY interpretation is much more complicated. The present study provides insights into the interpretation of the HATS5m descriptor (H-GETAWAY) concerning the molecular structures of the 4-thiazolidinone derivatives with antitrypanosomal activity. According to the published study, an increase in antitrypanosomal activity is associated with both a decrease and an increase in HATS5m (leverage-weighted autocorrelation with lag 5, weighted by atomic masses) values. The substructure-based method explored how the changes in molecular features affect the HATS5m value. Based on this approach, we proposed substituents that translate into low and high HATS5m. The detailed interpretation of H-GETAWAY descriptors requires the consideration of three elements: weighting scheme, leverages, and the Dirac delta function. Particular attention should be paid to the impact of chemical compounds’ size and shape and the leverage values of individual atoms.

show abstract

Antitumor activity of 3,4-ethylenedioxythiophene derivatives and quantitative structure-activity relationship analysis

Cited by 12 publications

References 34 publications

Deep Eutectic Solvents as Convenient Media for Synthesis of Novel Coumarinyl Schiff Bases and Their QSAR Studies

Deep Eutectic Solvents as Convenient Media for Synthesis of Novel Coumarinyl Schiff Bases and Their QSAR Studies

Design and Synthesis of Benzimidazole-Chalcone Derivatives as Potential Anticancer Agents

HATS5m as an Example of GETAWAY Molecular Descriptor in Assessing the Similarity/Diversity of the Structural Features of 4-Thiazolidinone

Contact Info

Product

Resources

About