Synthesis, Antiviral Bioactivity of Novel 4-Thioquinazoline Derivatives Containing Chalcone Moiety

A series of novel 4-thioquinazoline derivatives containing chalcone moiety were designed, synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited moderate to good anti-TMV activity. In particular, compounds M2 and M6 possessed appreciable protection activities against TMV in vivo, with 50% effective concentration (EC50) values of 138.1 and 154.8 μg/mL, respectively, which were superior to that of Ribavirin (436.0 μg/mL). The results indicated that chalcone derivatives containing 4-thioquinazoline moiety could effectively control TMV. Meanwhile, the structure-activity relationship (SAR) of the target compounds, studied using the three-dimensional quantitative structure-activity relationship (3D-QSAR) method of comparative molecular field analysis (CoMFA) based on the protection activities against TMV, demonstrated that the CoMFA model exhibited good predictive ability with the cross-validated q2 and non-cross-validated r2 values of 0.674 and 0.993, respectively. Meanwhile, the microscale thermophoresis (MST) experimental showed that the compound M6 may interaction with the tobacco mosaic virus coat protein (TMV CP).

• Publication year

  2015

• Venue

  Molecules

• Publication date

  2015-06-29

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.3390/molecules200711861PMID 26132908PMCID 6332188
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Flavonoids as noncompetitive inhibitors of Dengue virus NS2B-NS3 protease: inhibition kinetics and docking studies.

  2015cited by this paper
• Crystal Structure of a Four-Layer Aggregate of Engineered TMV CP Implies the Importance of Terminal Residues for Oligomer Assembly

  2013influential reference
• Hexachlorocyclotriphosphazene (HCCP)-Mediated Direct Formation of Thioethers and Ethers from Quinazolin-4(3H)-ones

  2013cited by this paper
• Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives

  2013cited by this paper
• Heteroaryl Chalcones: Design, Synthesis, X-ray Crystal Structures and Biological Evaluation

  2013cited by this paper
• Synthesis and Antibacterial Activity of Some Heterocyclic Chalcone Analogues Alone and in Combination with Antibiotics

  2012cited by this paper
• Inhibitory Evaluation of Sulfonamide Chalcones on β-Secretase and Acylcholinesterase

  2012cited by this paper
• Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives

  2011cited by this paper
• Molecular Design of Anticancer Drug Leads Based on Three-Dimensional Quantitative Structure-Activity Relationship

  2011cited by this paper
• Synthesis, cytotoxicity, and anti-Trypanosoma cruzi activity of new chalcones.

  2008cited by this paper
• Antibacterial activity of some 3-(arylideneamino)-2-phenylquinazoline-4(3H)-ones: synthesis and preliminary QSAR studies.

  2007cited by this paper
• Synthesis of isomeric, oxathiolone fused chalcones, and comparison of their activity toward various microorganisms and human cancer cells line.

  2007cited by this paper
• Synthesis and antifungal activity of novel s-substituted 6-fluoro-4-alkyl(aryl)thioquinazoline derivatives.

  2007cited by this paper
• Synthesis and bioactivity of 4-alkyl(aryl)thioquinazoline derivatives.

  2007influential reference
• Highly Predictive CoMFA and CoMSIA Models for Two Series of Stromelysin-1 (MMP-3) Inhibitors Elucidate S1' and S1-S2' Binding Modes

  2006cited by this paper
• Synthesis and antiviral activity of novel chiral cyanoacrylate derivatives.

  2005cited by this paper
• Antitrichomonal activity of 1,3-diaryl-2-propen-1-ones on Trichomonas gallinae

  2004cited by this paper
• SYNTHESIS AND BIOLOGICAL SCREENING OF SOME NEW SUBSTITUTED-3H-QUINAZOLIN-4-ONE ANALOGS AS ANTIMICROBIAL AGENTS

  2004cited by this paper
• Synthesis of Purine Antiviral Agents, Hypoxanthine and 6-Mercaptopurine

  2002cited by this paper
• [Chalcones and their heterocyclic analogs as potential therapeutic agents in bacterial diseases].

  2000cited by this paper
• 100 years of virology: from vitalism via molecular biology to genetic engineering.

  2000cited by this paper
• Comparative studies of inhibitory activities of chalcones on tomato ringspot virus (ToRSV)

  1997cited by this paper
• Inhibition of tomato ringspot virus by flavonoids

  1996cited by this paper
• Inhibition of infectivity of potato virus X by flavonoids

  1992cited by this paper
• Predictive ability of regression models. Part II: Selection of the best predictive PLS model

  1992cited by this paper
• Predictive ability of regression models. Part I: Standard deviation of prediction errors (SDEP)

  1992cited by this paper
• Flavonoids inhibit infectivity of tobacco mosaic virus.

  1991cited by this paper
• The synthesis of some quinazoline derivatives and their biological properties

  1983cited by this paper
• Study on the effect of flavonoids on the infectivity of potato virus X.

  1973cited by this paper

• Iodine-Promoted Intermolecular Cyclization for the Synthesis of 2-Phenylquinazolines

  2025cites this paper
• Amide linked chalcone derivatives, a promising class of compounds with versatile biological effects

  2025cites this paper
• Synthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studies

  2025cites this paper
• Recent advances in the pesticide activities of chalcone derivatives

  2025cites this paper
• Synthesis, molecular docking, assessment of biological and anti-diabetic properties of benzalacetophenone derivatives

  2025cites this paper
• Discovery of Potential Antifungal Agents: Chalcone Derivatives Containing Thiourea and Piperidine Moieties.

  2025cites this paper
• Targeting Blood‐Stage Malaria: Design, Synthesis, Characterization, In Vitro, and In Silico Evaluation of Pyrrolidinodiazenyl Chalcones

  2025cites this paper
• BPR3P0128, a non-nucleoside RNA-dependent RNA polymerase inhibitor, inhibits SARS-CoV-2 variants of concern and exerts synergistic antiviral activity in combination with remdesivir

  2024cites this paper
• Design, synthesis and antifungal activity of indole derivatives containing 1,3,4-oxadiazole

  2024cites this paper
• Design, synthesis, X-ray crystal structure, and antifungal evaluation of new acetohydrazide derivatives containing a 4-thioquinazoline moiety.

  2024cites this paper
• One-pot green synthesis, biological evaluation, and in silico study of pyrazole derivatives obtained from chalcones

  2024cites this paper
• Synthesis of 4-(Phenylamino)quinazoline-2(1H)-thiones Using Green Solvents.

  2024cites this paper
• N-Heterocycles as Promising Antiviral Agents: A Comprehensive Overview

  2024cites this paper
• New 1,3,4‒oxadiazole Quinazolines as Potential Anticancer Agents: Design, Synthesis, Biological Evaluation, and In silico Studies.

  2024cites this paper
• Antiviral activity evaluation and action mechanism of chalcone derivatives containing phenoxypyridine

  2024cites this paper
• Design, synthesis and biological evaluation of novel hybrids of quinazoline derivatives and phenylsulfonylfuroxan as potential anti-tumor agents

  2023cites this paper
• Transition-metal-catalyzed synthesis of quinazolines: A review

  2023cites this paper
• Myricetin derivatives containing the benzoxazinone moiety discovered as potential anti-tobacco mosaic virus agents.

  2023cites this paper
• Design, synthesis, and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moiety

  2023cites this paper
• Time-resolved spectroscopic and computational study of the initial events in doxazosin photochemistry.

  2023cites this paper
• Design, synthesis, and antiviral activities evaluation of novel quinazoline derivatives containing sulfonamide moiety

  2023cites this paper
• Packing Preferences of Chalcones: A Model Conjugated Pharmaceutical Scaffold

  2022cites this paper
• Phenolic compounds

  2022cites this paper
• Synthesis and Antitumor Activity Evaluation of 2,4,6-Trisubstituted Quinazoline Derivatives Containing Thiazole Structure

  2022cites this paper
• Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

  2022cites this paper
• An update on inhibitors targeting RNA-dependent RNA polymerase for COVID-19 treatment: Promises and challenges

  2022cites this paper
• Synthesis, reaction, antimicrobial, and docking study of new chalcones incorporating isoquinoline moiety

  2022cites this paper
• A Fluorescence and Molecular Docking Study on the Interaction of 4′-Hydroxychalcone with Bovine Serum Albumin and Human Serum Albumin

  2022cites this paper
• Plant Secondary Metabolites as a Tool to Investigate Biotic Stress Tolerance in Plants: A Review

  2022cites this paper
• Recent research progress and outlook in agricultural chemical discovery based on quinazoline scaffold.

  2022cites this paper
• Computational Study on Molecular Structure, UV-Visible and Vibrational Spectra and Frontier Molecular Orbital Analysis of (E)-7-((2-Chloroquinolin-3-yl)methylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

  2022cites this paper
• Spectral Study and Theoretical Treatment of 2-( 2-( 4-bromocyclohexa-1 , 3-dienyl )-4-oxo-2 H-benz [ 1 , 3 ] oxazin-3 ( 4 H )-ylamino )-2-oxoethyl carbamimidothioate and Derivatives

  2022cites this paper
• Antibacterial, Docking, DFT and ADMET Properties Evaluation of Chalcone-Sulfonamide Derivatives Prepared Using ZnO Nanoparticle Catalysis

  2021cites this paper
• Synthesis and anticancer activity of chalcone–quinoxalin conjugates

  2021cites this paper
• Secondary metabolites as biostimulant and bioprotectant agents: A review

  2021cites this paper
• Chalcones: A review on synthesis and pharmacological activities

  2021cites this paper
• Recent achievements on the agricultural applications of thioether derivatives: A 2010–2020 decade in review

  2021cites this paper
• Antiviral Agents – Benzazine Derivatives

  2021cites this paper
• The Dimroth Rearrangement in the Synthesis of Condensed Pyrimidines – Structural Analogs of Antiviral Compounds

  2021cites this paper
• Quinoline and Quinazoline Derivatives Inhibit Viral RNA Synthesis by SARS-CoV-2 RdRp

  2021cites this paper
• Synthesis & Structure-Photophysics Evaluation on 2-N-Aminoquinazolines - Small-Molecule Fluorophores for Solution and Solid State.

  2021cites this paper
• Insights on a new sulfonamide chalcone with potential antineoplastic application

  2021cites this paper
• 3D-QSAR, molecular docking and in silico ADMET studies of propiophenone derivatives with anti-HIV-1 protease activity

  2021cites this paper
• An overview of triazoloquinazolines: Pharmacological significance and recent developments.

  2021cites this paper
• Electronic, reactivity and third order nonlinear optical properties of thermally-stable push-pull chalcones for optoelectronic interest: Experimental and DFT assessments

  2021cites this paper
• Synthesis of Alicyclic 2-Methylenethiazolo[2,3-b]quinazolinone Derivatives via Base-Promoted Cascade Reactions

  2021cites this paper
• New chalcone derivatives: synthesis, antiviral activity and mechanism of action

  2020cites this paper
• Synthesis and Biological Investigation of Novel Adamantylated Heterocyclic Rings with Chalcone Based Structure

  2020cites this paper
• The Quinazoline-Chalcone and Quinazolinone-Chalcone Hybrids: A Promising Combination for Biological Activity.

  2020cites this paper
• Experimental and Theoretical Studies on the Molecular Structure, FT-IR, NMR, HOMO, LUMO, MESP, and Reactivity Descriptors of (E)-1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

  2020cites this paper
• The Molecular Docking, Synthesis and anti-HIV-1 protease Activity of Novel Chalcones.

  2020cites this paper
• Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole

  2020cites this paper
• Microwave-assisted three component synthesis of novel bis-fused quinazolin-8(4H)-ones linked to aliphatic or aromatic spacer via amide linkages

  2020cites this paper
• Design, synthesis and anti-influenza A virus activity of novel 2,4-disubstituted quinazoline derivatives.

  2020cites this paper
• Ultrasound Promoted Stereoselective Synthesis of 2,3-Dihydrobenzofuran Appended Chalcones at Ambient Temperature

  2020cites this paper
• Synthesis of Functionalized 2,3-Dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-one via Intramolecular Electrophilic Cyclization

  2020cites this paper
• Color Differences Highlight Concomitant Polymorphism of Chalcones

  2020cites this paper
• Phenolic Compounds Against Fungal and Viral Plant Diseases

  2020cites this paper
• Molecular modelling and optical properties of a novel fluorinated chalcone

  2020cites this paper
• Proteomic and Phosphoproteomic Analysis in Tobacco Mosaic Virus-Infected Tobacco (Nicotiana tabacum)

  2019cites this paper
• Crystal structure, spectroscopic analyses, linear and third-order nonlinear optical properties of anthracene-based chalcone derivative for visible laser protection

  2019cites this paper
• Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and antiviral activities

  2019cites this paper
• Silver-Catalyzed Annulation of Arynes with Nitriles for Synthesis of Structurally Diverse Quinazolines.

  2019cites this paper
• New 1,2,4-triazole-Chalcone hybrids induce Caspase-3 dependent apoptosis in A549 human lung adenocarcinoma cells.

  2018cites this paper
• Solvent-Free Synthesis and Antiviral Activity of Chiral Dialkyl 2-(Substituted-((4-(Pyridin-3-Yl)Pyrimidin-2-Yl)Amino)Methyl) Malonate

  2018cites this paper
• Cyclization of mercaptopyrimidine derivative: a facile synthetic approach for condensed pyrimidines

  2018cites this paper
• Evaluation of chalcones as inhibitors of glutathione S‐transferase

  2018cites this paper
• Synthesis and three-dimensional quantitative structure-activity relationship study of quinazoline derivatives containing a 1,3,4-oxadiazole moiety as efficient inhibitors against Xanthomonas axonopodis pv. citri

  2018cites this paper
• Antiviral properties and interaction of novel chalcone derivatives containing a purine and benzenesulfonamide moiety.

  2018cites this paper
• Synthesis and antiviral bioactivity of novel chalcone derivatives containing purine moiety

  2018cites this paper
• An overview of quinazolines: Pharmacological significance and recent developments.

  2018cites this paper
• Study of the synthesis, antiviral bioactivity and interaction mechanisms of novel chalcone derivatives that contain the 1,1-dichloropropene moiety

  2017cites this paper
• Synthesis and antiviral evaluation of novel 1,3,4-oxadiazole/thiadiazole-chalcone conjugates.

  2017cites this paper
• Molecular structure, second- and third-order nonlinear optical properties and DFT studies of a novel non-centrosymmetric chalcone derivative: (2E)-3-(4-fluorophenyl)-1-(4-{[(1E)-(4-fluorophenyl)methylene]amino}phenyl)prop-2-en-1-one.

  2017cites this paper
• Design, synthesis, antiviral bioactivity and three-dimensional quantitative structure-activity relationship study of novel ferulic acid ester derivatives containing quinazoline moiety.

  2017cites this paper
• Design, synthesis, docking studies and biological evaluation of novel chalcone derivatives as potential histone deacetylase inhibitors.

  2017cites this paper
• Design and Development of a Novel Chalcone Derivative as an Anticholinesterase Inhibitor for Possible Treatment of Dementia

  2017cites this paper
• Biophysics: for HTS hit validation, chemical lead optimization, and beyond

  2017cites this paper
• Novel trans-Ferulic Acid Derivatives Containing a Chalcone Moiety as Potential Activator for Plant Resistance Induction.

  2017cites this paper
• Chalcone: A Privileged Structure in Medicinal Chemistry.

  2017cites this paper
• Synthesis of 8-Trifluloromethyl-2-Thioquinazolin-(3H)-4-One Nucleosides

  2017cites this paper
• Design, Synthesis, and Antiviral Activity of Novel Chalcone Derivatives Containing a Purine Moiety

  2017cites this paper
• Discovery of novel double pyrazole Schiff base derivatives as anti-tobacco mosaic virus (TMV) agents

  2017cites this paper
• Chemical outbreak for tobacco mosaic virus control

  2017cites this paper
• Recent advances on the synthesis and pesticidal activity evaluations of quinazoline derivatives

  2017cites this paper
• Synthesis and investigation of the antibacterial activity and action mechanism of 1,3,4-oxadiazole thioether derivatives.

  2017cites this paper
• Synthesis, electronic, and spectral properties of novel geranylated chalcone derivatives: a theoretical and experimental study

  2016cites this paper
• SYNTHESIS, ANTIMICROBIAL ACTIVITY AND MOLECULAR DOCKING STUDY OF SOME NEW N-BENZYL AND N-BENZOYL-3-INDOLYL HETEROCYCLES

  2016cites this paper
• Quinazoline pharmacophore in therapeutic medicine

  2016cites this paper
• Synthesis and antiviral activity of novel thioether derivatives containing 1,3,4-oxadiazole/thiadiazole and emodin moieties

  2016cites this paper
• Medicinal Chemistry Research Synthesis and Evaluation of Antibacterial and Antifungal Activities of 4-thiazolidinones and 2-azetidinones Derivatives from Chalcone

  year unknowncites this paper