Synthesis of 3-(2-Alkylthio-4-chloro-5-methylbenzenesulfonyl)-2-(1-phenyl-3-arylprop-2-enylideneamino)guanidine Derivatives with Pro-Apoptotic Activity against Cancer Cells

Synthesis of 3-(2-Alkylthio-4-chloro-5-methylbenzenesulfonyl)-2-(1-phenyl-3-arylprop-2-enylideneamino)guanidine Derivatives with Pro-Apoptotic Activity against Cancer Cells

The untypical course of reaction between chalcones and benzenesulfonylaminoguanidines led to the new 3-(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)-2-(1-phenyl-3-arylprop-2-enylideneamino)guanidine derivatives <b>8</b>–<b>33</b>. The new compounds were tested in vitro for t...

Full description

Bibliographic Details
Main Authors:	Aneta Pogorzelska, Jarosław Sławiński, Anna Kawiak, Grzegorz Stasiłojć, Jarosław Chojnacki
Format:	Article
Language:	English
Published:	MDPI AG 2023-02-01
Series:	International Journal of Molecular Sciences
Subjects:	benzenesulfonamides benzenesulfonylguanidines amidrazones anticancer activity cytotoxicity cell cycle flow cytometry analysis
Online Access:	https://www.mdpi.com/1422-0067/24/5/4436

Similar Items

New <i>N</i>-Benzenesulfonylguanidine Derivatives and Their Selective Growth Inhibition of Human Breast Cancer Cell Line MCF-7 and Colon Carcinoma HCT-116
by: Aneta Pogorzelska, et al.
Published: (2022-11-01)

Novel 2-alkythio-4-chloro-<i>N</i>-[imino(heteroaryl)methyl]benzenesulfonamide Derivatives: Synthesis, Molecular Structure, Anticancer Activity and Metabolic Stability
by: Beata Żołnowska, et al.
Published: (2023-06-01)

Synthesis of New <i>N</i>-Substituted <i>N</i>′-(2-methylthio-4-chloro-5-methylbenzenesulfonyl)guanidines with Anticancer Activity
by: Beata Żołnowska, et al.
Published: (2022-11-01)

New 2-[(4-Amino-6-<i>N</i>-substituted-1,3,5-triazin-2-yl)methylthio]-<i>N</i>-(imidazolidin-2-ylidene)-4-chloro-5-methylbenzenesulfonamide Derivatives, Design, Synthesis and Anticancer Evaluation
by: Łukasz Tomorowicz, et al.
Published: (2022-06-01)

Evaluation of the Antimicrobial Activity of <i>N</i>-Acylated 4-Chloro-2-mercaptobenzenesulfonamide Derivatives
by: Anita Bułakowska, et al.
Published: (2022-11-01)

Synthesis, Antitumor Evaluation, Molecular Modeling and Quantitative Structure–Activity Relationship (QSAR) of Novel 2-[(4-Amino-6-<i>N</i>-substituted-1,3,5-triazin-2-yl)methylthio]-4-chloro-5-methyl-<i>N</i>-(1<i>H</i>-benzo[<i>d</i>]imidazol-2(3<i>H</i>)-ylidene)Benzenesulfonamides
by: Łukasz Tomorowicz, et al.
Published: (2020-04-01)

Novel 5-Substituted 2-(Aylmethylthio)-4-chloro-N-(5-aryl-1,2,4-triazin-3-yl)benzenesulfonamides: Synthesis, Molecular Structure, Anticancer Activity, Apoptosis-Inducing Activity and Metabolic Stability
by: Beata Żołnowska, et al.
Published: (2016-06-01)

Crystal structure of N-(3-chloro-1-methyl-1H-indazol-5-yl)-4-methoxybenzenesulfonamide
by: Hakima Chicha, et al.
Published: (2014-09-01)

New Chalcone Derivatives Containing 2,4-Dichlorobenzenesulfonamide Moiety with Anticancer and Antioxidant Properties
by: Anita Bułakowska, et al.
Published: (2023-12-01)

The Synthesis and Biological Activity of Amidrazone Derivatives Obtained in Reaction with <i>cis</i>-1,2,3,6-Tetrahydrophthalic Anhydride
by: Renata Paprocka, et al.
Published: (2022-11-01)

Synthesis and Anti-Yeast Evaluation of Novel 2-Alkylthio-4-chloro-5-methyl-N-[imino-(1-oxo-(1H)-phthalazin-2-yl)methyl]benzenesulfonamide Derivatives
by: Jarosław Sławiński, et al.
Published: (2014-09-01)

7-Chloro-3-(4-methylbenzenesulfonyl)pyrrolo[1,2-c]pyrimidine
by: Easha Narayan, et al.
Published: (2020-03-01)

A Review of the Biological Activity of Amidrazone Derivatives
by: Renata Paprocka, et al.
Published: (2022-09-01)

First Synthesis of 3-Glycopyranosyl-1,2,4-Triazines and Some Cycloadditions Thereof
by: Éva Bokor, et al.
Published: (2022-11-01)

Design, synthesis, and antimicrobial screening of novel pyridyl-2-amidrazone incorporated isatin mannich bases
by: N Saravana Kumar, et al.
Published: (2012-01-01)

Synthesis and Structure of <i>N</i>-(1-(Bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)benzenesulfonamide
by: Ivan A. Garagan, et al.
Published: (2023-05-01)

Some Anilides of 2-Alkylthio- and 2-Chloro-6-Alkylthio-4-Pyridinecarboxylic Acids: Synthesis and Photosynthesis-Inhibiting Activity
by: MiloÃ…Â¡ MachÃƒÂ¡Ã„Âek, et al.
Published: (2001-06-01)

Evaluation of Anthelmintic and Anti-Inflammatory Activity of 1,2,4-Triazole Derivatives
by: Renata Paprocka, et al.
Published: (2022-07-01)

An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide
by: Reham A. Mohamed-Ezzat, et al.
Published: (2024-02-01)

Designing, synthesis and bioactivities of 4-[3-(4-hydroxyphenyl)-5-aryl-4,5-dihydro-pyrazol-1-yl]benzenesulfonamides
by: Halise Inci Gul, et al.
Published: (2017-01-01)

Synthesis, characterization and antimicrobial activity of some new 4-(4-(2-isonicotinoylhydrazinyl)-6-((aryl)amino)-1,3,5-triazin-2-ylamino)-N-(pyrimidin-2-yl) benzenesulfonamides
by: N.C. Desai, et al.
Published: (2017-01-01)

Benzo[g]quinazolin-based scaffold derivatives as dual EGFR/HER2 inhibitors
by: Mostafa M. Ghorab, et al.
Published: (2018-01-01)

Design, Synthesis and Anti-HIV Integrase Evaluation of N-(5-Chloro-8-Hydroxy-2-Styrylquinolin-7-yl)Benzenesulfonamide Derivatives
by: Li-Ming Hu, et al.
Published: (2010-03-01)

Exploration of Benzenesulfonamide-Bearing Imidazole Derivatives Activity in Triple-Negative Breast Cancer and Melanoma 2D and 3D Cell Cultures
by: Benas Balandis, et al.
Published: (2021-11-01)

Novel 3-Amino-6-chloro-7-(azol-2 or 5-yl)-1,1-dioxo-1,4,2-benzodithiazine Derivatives with Anticancer Activity: Synthesis and QSAR Study
by: Aneta Pogorzelska, et al.
Published: (2015-12-01)

Evaluation of Biological Activity of New 1,2,4-Triazole Derivatives Containing Propionic Acid Moiety
by: Renata Paprocka, et al.
Published: (2023-04-01)

Efficient Routes to Pyrazolo[3,4-e][1,2,4]triazines and a New Ring System: [1,2,4]Triazino[5,6-d][1,2,3]triazines
by: Hamad Mohamed Al-Matar, et al.
Published: (2010-05-01)

Synthesis and QSAR Study of Novel 6-Chloro-3-(2-Arylmethylene-1-methylhydrazino)-1,4,2-benzodithiazine 1,1-Dioxide Derivatives with Anticancer Activity
by: Jarosław Sławiński, et al.
Published: (2015-04-01)

Triapine Derivatives Act as Copper Delivery Vehicles to Induce Deadly Metal Overload in Cancer Cells
by: Kateryna Ohui, et al.
Published: (2020-09-01)

Synthesis and Antimicrobial Evaluation of Some New Pyrazolo[1,5-a]pyrimidine and Pyrazolo[1,5-c]triazine Derivatives Containing Sulfathiazole Moiety
by: Elsherbiny Hamdy El-Sayed, et al.
Published: (2020-12-01)

Discovery of a Novel Benzenesulfonamide Analogue That Inhibits Proliferation and Metastasis Against Ovarian Cancer OVCAR-8 Cells
by: Jia Y, et al.
Published: (2020-01-01)

Design, synthesis and biological evaluation of novel biphenylsulfonamide derivatives as selective AT2 receptor antagonists
by: Danhui Wang, et al.
Published: (2022-08-01)

Crystal structure and Hirshfeld surface analysis of N,N′-[ethane-1,2-diylbis(oxy)]bis(4-methylbenzenesulfonamide)
by: Seher Meral, et al.
Published: (2019-01-01)

Synthesis, characterization and antimicrobial activity of some novel 4-(4-(arylamino)-6-(piperidin-1-yl)-1,3,5-triazine-2-ylamino)-N-(pyrimidin-2-yl)benzenesulfonamides
by: N.C. Desai, et al.
Published: (2016-11-01)

Synthesis and Structural Study of Amidrazone Derived Pyrrole-2,5-Dione Derivatives: Potential Anti-Inflammatory Agents
by: Renata Paprocka, et al.
Published: (2022-04-01)

Design, synthesis, cytotoxic evaluation and molecular docking of novel 1, 3, 4-thiadiazole sulfonamides with azene and coumarin moieties as carbonic anhydrase inhibitors
by: Samir Bondock, et al.
Published: (2023-08-01)

Novel benzofuran-based sulphonamides as selective carbonic anhydrases IX and XII inhibitors: synthesis and in vitro biological evaluation
by: Mohamed A. Abdelrahman, et al.
Published: (2020-01-01)

Unprecedented synthesis of a 14-membered hexaazamacrocycle
by: Anastasia A. Fesenko, et al.
Published: (2023-11-01)

Crystal structure of N-{[3-bromo-1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide
by: M. Umadevi, et al.
Published: (2015-10-01)

Synthesis and Monoamine Oxidase Inhibition Properties of 4-(2-Methyloxazol-4-yl)benzenesulfonamide
by: Anton A. Shetnev, et al.
Published: (2024-03-01)