Molecular structures, Hirshfeld analysis and biological investigations of isatin based thiosemicarbazones

Sivaraj, Saranya; Haribabu, Jebiti; Palakkeezhillam, Vishnunarayanan Namboothiri Vadakkedathu; Peter, Jerome; Gomathi, K.; Rao, Kodagala Kameswara; Babu, Velakaturi Hari Hara Surendra; Karvembu, Ramasamy; Gayathri, D.

doi:10.1016/j.molstruc.2019.126904

Cited by 24 publications

(10 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The central skeleton of thiosemicarbazone derivatives is a NNHC(S)NH structure, which makes them used as drugs and useful model for bioinorganic processes. Their biological activities usually manifest as antibacterial, [ 1–4 ] anti‐inflammatory, [ 4–6 ] anticancer, [ 1,7,8 ] antiviral, [ 9,10 ] and anti‐proliferative activity. [ 11 ] Further, not only thiosemicarbazone itself but also the multichelate formed by the coordination of its ligand with the metal has good activity.…”

Section: Introductionmentioning

confidence: 99%

Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies

Wang

Zhang

Fan

et al. 2020

J of Physical Organic Chem

View full text Add to dashboard Cite

Two novel thiosemicarbazone derivatives (E)‐N‐(3,5‐dimethylphenyl)‐2‐(3‐methylbenzylidene)thiosemicar‐bazone (1) and (E)‐N‐(3,5‐dimethylphenyl)‐2‐(3‐fluorobenzylidene)thiosemicarbazone (2) had been synthesized and characterized by FT‐IR, nuclear magnetic resonance, and elemental analysis. Single crystal X‐ray diffraction analysis showed that compound 1 belongs to triclinic system in P‐1 space group and compound 2 belongs to monoclinic system in C2/c space group. It could be seen from the determined crystal structure that the central skeleton NNHC(S)NH of both thiosemicarbazone compounds have good planarity. Density functional theory (DFT) calculations were done using B3LYP/6‐31+G(d, p) basis set and the calculated results are in good agreement with the experimental data. In addition, the UV‐visible absorption spectrum was estimated based on TD‐DFT quantum chemistry calculations. Likewise, the simulated absorption spectrum is very consistent with the experimental data. Combining Hirshfeld surface analysis and molecular structure, it was found that the intermolecular hydrogen bond NH···SC constitutes central symmetric dimer . Through quantum chemical calculation, we investigated the reduced density gradient function and the independent gradient model, which provided a deeper insight into the intermolecular and intramolecular interaction force of the compounds. The frontier molecular orbital analysis and molecular electrostatic potential were also discussed by theoretical calculations.

show abstract

Section: Introductionmentioning

confidence: 99%

Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies

Wang

Zhang

Fan

et al. 2020

J of Physical Organic Chem

View full text Add to dashboard Cite

show abstract

“…Molecular docking, a subfield of computational chemistry and bioscience, is a powerful tool to investigate and provide several quick insights into ligand–receptor interactions in order to facilitate the design of potential drugs. 36,37…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a novel hydrazone-based compound applied as a fluorescence turn-on chemosensor for iron(iii) and a colorimetric sensor for copper(ii) with antimicrobial, DFT and molecular docking studies

et al. 2023

View full text Add to dashboard Cite

show abstract

“…The isatin–(thio)semicarbazone hybrids also showed potential anticancer activity, [ 51–60 ] and the representative compound 13a (NSC73306, IC 50 : 2.23–22.40 μM and 0.99–36.79 μM against drug‐sensitive and drug‐resistant cancer cell lines, respectively, MTT assay) possessed promising activity against a panel of drug‐sensitive and ‐resistant (express human P‐glycoprotein [P‐gp]) cancer cell lines and the activity was comparable to that of doxorubicin (IC 50 : 0.24–17.32 μM) against drug‐resistant cancer cell lines. [ 51,52 ] Further study indicated that hybrids 13b,c (IC 50 : 1.07–17.15 μM, MTT assay) also showed potential activity against parental KB‐3‐1 and the P‐gp‐expressing KB‐V1 cancer cell lines and they were 8.3‐ and 14.8‐fold more active against P‐gp‐expressing KB‐V1 cells than against KB‐3‐1 cells, implying these hybrids could act as potential P‐gp inhibitors.…”

Section: Isatin–coumarin Hybridsmentioning

confidence: 99%

Recent advances in isatin hybrids as potential anticancer agents

Ding

Zhou

Zeng

2020

Archiv der Pharmazie

View full text Add to dashboard Cite

The isatin framework is a useful template for the development of novel anticancer agents. This is exemplified by the fact that several isatin‐based anticancer agents, such as semaxanib, sunitinib, nintedanib, and hesperadin, are already in use or under clinical trials for the treatment of diverse kinds of cancers. Isatin‐based hybrids could be obtained by incorporating other anticancer pharmacophores into the isatin skeleton and they have the potential to overcome drug resistance with reduced side effects. Thus, isatin‐based hybrids may provide attractive scaffolds for the development of novel anticancer agents. This review covers the recent advances of isatin‐based hybrids with anticancer activity, covering articles published between 2001 and 2019. The anticancer activities of these molecules and the structure–activity relationships are also discussed. The purpose of this review article is to set up the direction for the design and development of isatin‐based hybrids with high efficacy and low toxicity.

show abstract

Molecular structures, Hirshfeld analysis and biological investigations of isatin based thiosemicarbazones

Cited by 24 publications

References 44 publications

Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies

Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies

Synthesis of a novel hydrazone-based compound applied as a fluorescence turn-on chemosensor for iron(iii) and a colorimetric sensor for copper(ii) with antimicrobial, DFT and molecular docking studies

Recent advances in isatin hybrids as potential anticancer agents

Contact Info

Product

Resources

About