Synthesis, in silico and in vitro studies of piperazinyl thiourea derivatives as apoptosis inducer for the treatment of colorectal carcinoma

Sashankh, Penki Venkata Sai; Dorairaj, Dorothy Priyanka; Chen, Jiaying; Chang, Yu-Lan; Chand, Kuldeep; Karvembu, Ramasamy; Chien, Ching-Ming; Hsu, Sodio C. N.

doi:10.1016/j.molstruc.2022.133086

Cited by 5 publications

(3 citation statements)

References 64 publications

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“…59). 61 A series of Pd metal complexes synthesized by Dorairaj et al were evaluated for their anticancer activity against MCF7 (breast), HeLa (cervical), A549 (lung) cancer HEK-293 (human embryonic kidney) normal cells. The activity of the compounds was found to a dose-dependent when incubated for 24 h, and IC 50 values of the synthesized complexes were in the range of 8.6-12.4 mM against HeLa, MCF7 and A549 cells and selectively targeted cancer cells.…”

Section: Biological Aspectsmentioning

confidence: 99%

“…59). 61 N,N-Di-2,4-dimethoxybenzyl-N 0 -2-nitrobenzoylthiourea (88) was synthesized by Arslan and Binzet by reacting 4-nitrobenzoyl isothiocyanate with bis(2,4-dimethoxybenzyl)amine in dry acetone. XRD analysis posed that the title compound crystallized in a triclinic crystal system and adopted the P 1 space group, carbonyl and thiocarbonyl tend to stay in opposite directions, and extensive delocalization was present at the acyl thiourea part of the molecule as indicated by the bond lengths, and crystal packing is due to intermolecular H-bonding among molecules (Fig.…”

Section: Molecular and Crystal Structurementioning

confidence: 99%

See 1 more Smart Citation

Exploring the latest trends in chemistry, structure, coordination, and diverse applications of 1-acyl-3-substituted thioureas: a comprehensive review

Ullah,

Saeed,

Azeem

et al. 2024

RSC Adv.

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Section: Biological Aspectsmentioning

confidence: 99%

Section: Molecular and Crystal Structurementioning

confidence: 99%

Exploring the latest trends in chemistry, structure, coordination, and diverse applications of 1-acyl-3-substituted thioureas: a comprehensive review

Ullah,

Saeed,

Azeem

et al. 2024

RSC Adv.

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show abstract

“…In the rst step, energy minimization was carried out using a smart minimizer with 1000 maximum steps and a RMS gradient of 0.001. Then, the compound-RBD complex was placed in an orthorhombic box and solvated with an explicit periodic boundary solvation water model [27]. Sodium and chloride ions were added to the system at a salt concentration of 0.145.…”

Section: Simulationmentioning

confidence: 99%

Targeting the Receptor Binding Domain and Heparan Sulfate Binding for Antiviral Drug Development against SARS-CoV-2 Variants

Yang

Chang

et al. 2023

Preprint

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SARS-CoV-2 is a highly infectious virus responsible for the COVID − 19 pandemic. The increased transmission rate led to the emergence of SARS-CoV-2 variants. In viral infection, the receptor-binding domain (RBD) proteins are essential role in binding to the host receptor. Others, Heparan sulfate (HS), widely distributed on the surface of host cells, is thought to play an important role in the viral infection cycle of SARS-CoV-2. Therefore, it might be a reasonable strategy for antiviral drug design to interference with the RBD in the HS binding site. In this study, we used computational approaches to analyze multiple sequences of coronaviruses and reveal important information about the binding of HS to RBD in the SARS-CoV-2 spike protein. Our results showed that the potential hot-spots, including F456, R457 and S459 in RBD, exhibited strong interactions in the HS-RBD binding region. Therefore, we screened different compounds in the natural product database towards these hot-spots to find potential antiviral candidates using LibDock and MD simulation in Discovery Studio 2019. The results showed six potential natural compounds, including acetoside, chrysin 6-C-arabinoside 8-C-glucoside (CAG), hyperoside, isoquercitrin, oroxyloside and chrysin 6-C-glucoside 8-C-arabinoside (CGA) had strong binding ability to the RBD. Our results demonstrate a feasible approach to identify potential antiviral agents through the evaluation of the binding interaction between viral glycoproteins and host receptors. The present study provided the applications of the structure-based computational approach for the design and development of new antiviral drugs against SARS-CoV-2 variants.

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Effect of Terminal Hydroxy Groups on the Structural Properties of Acyl Thioureas

Nossa González,

Gómez Castaño,

Echeverria

et al. 2024

ChemPhysChem

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The 1‐acyl thiourea family [R1C(O)NHC(S)NR2R3] exhibits the flexibility to incorporate a wide variety of substituents into their structure. The structural attributes of these compounds are intricately tied to the type and extent of substitution. In the case of 3‐mono‐substituted thioureas (R2 = H), the conformational behavior is predominantly shaped by the presence of an intramolecular N–H···O=C hydrogen bond. This study delves into the structural consequences stemming from the inclusion of substituents possessing hydrogen‐donor capabilities within four novel 1‐acyl‐3‐mono‐substituted thiourea derivatives. A comprehensive suite of analytical techniques, encompassing FTIR, Raman spectroscopy, multinuclear (1H and 13C) NMR spectroscopy, single‐crystal X‐ray diffraction, and supported by computational methods, notably NBO (Natural Bond Orbital) population analysis, Hirshfeld analysis, and QTAIM (Quantum Theory of Atoms in Molecules), was harnessed to scrutinize and characterize these compounds. In the crystalline state, these compounds exhibit an intricate interplay of intermolecular interactions, prominently featuring an expansive network of hydrogen bonds between the hydroxy (‐OH) groups and the carbonyl and thiocarbonyl bonds within the 1‐acyl thiourea fragment. Notably, the topological analysis underscores significant distinctions in the properties of the acyl thiourea fragment and the intramolecular >C=O···H‐N bond when transitioning from the isolated molecule to the crystalline environment.

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Synthesis, in silico and in vitro studies of piperazinyl thiourea derivatives as apoptosis inducer for the treatment of colorectal carcinoma

Cited by 5 publications

References 64 publications

Exploring the latest trends in chemistry, structure, coordination, and diverse applications of 1-acyl-3-substituted thioureas: a comprehensive review

Exploring the latest trends in chemistry, structure, coordination, and diverse applications of 1-acyl-3-substituted thioureas: a comprehensive review

Targeting the Receptor Binding Domain and Heparan Sulfate Binding for Antiviral Drug Development against SARS-CoV-2 Variants

Effect of Terminal Hydroxy Groups on the Structural Properties of Acyl Thioureas

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