Design and Synthesis of Novel Thioureas Derived from 4‐(4‐Fluorophenoxy)aniline as Anticancer Agents

Yıldız, İnci Nejla; Oruç‐Emre, Emine Elçin; Tasdemir, D; Karaküçük‐İyidoğan, Ayşegül; Ulaşlı, Mustafa; Bayram, Hasan

doi:10.1002/jccs.201600193

Cited by 6 publications

(7 citation statements)

References 26 publications

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“…The peaks were observed due to the specific fragmentations of compounds seen in Supporting Information Figure S2. The fragmentation patterns were compatible with the literature . For the thiourea derivatives, the bond between NH and CS was cleaved and the H atom on the nitrogen migrated to the other NH and isothiocyanate and amine were formed.…”

Section: Resultssupporting

confidence: 83%

Design and evaluation of biological activities of 1,3‐oxazolidinone derivatives bearing amide, sulfonamide, and thiourea moieties

Karaman

Zainel

Kapkac

et al. 2018

Archiv der Pharmazie

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1,3-Oxazolidine-2-one is an important heterocyclic ring participating in the chemical structure of many drugs. In this research, 22 new amide/sulfonamide/thiourea derivatives (1-22) were obtained by the reaction of (S)-4-(4-aminobenzyl)-2(1H)-1,3-oxazolidinone with 4-substituted benzoyl chlorides, 4-substituted benzene sulfonyl chlorides, and 4-substituted phenyl isothiocyanates. The structures of all synthesized compounds were clarified by FT-IR, NMR, and mass spectroscopic and elemental analysis techniques. The synthesized compounds were screened for their antimicrobial activity. Antimicrobial susceptibility and cellular physiology were evaluated using the microbroth dilution assay and the flow cytometry method. As a result, it was determined that compound 16 displayed better antimicrobial activity than chloramphenicol against Gram-positive bacteria, especially Staphylococcus aureus. In order to understand the mechanism of effect of the compounds on the cell membrane, fluorescence microscopy was used. Cell membrane damage of the Gram positive bacteria treated with compound 16 was observed as a result of intense staining with propidium iodide. In addition, genotoxicity, cytotoxicity, and absorption, distribution, metabolism, and excretion (ADME) parameters of compound 16 were examined and it was found as non-mutagenic and non-cytotoxic at the concentration at which it showed antimicrobial activity. According to the calculated ADME parameters and drug likeness scores, the compounds can be good drug candidates, especially compound 16.

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Section: Resultssupporting

confidence: 83%

Design and evaluation of biological activities of 1,3‐oxazolidinone derivatives bearing amide, sulfonamide, and thiourea moieties

Karaman

Zainel

Kapkac

et al. 2018

Archiv der Pharmazie

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“…The synthetic pathway of target compounds is outlined in Scheme 1. The chiral thiourea derivatives were obtained according to the literature [27,28] and then reacted with oxalyl chloride to obtain chiral 1,3‐thiazolidine‐4,5‐diones derivatives [29,30] . The compounds were characterized by FT‐IR, NMR, mass spectra, and elemental analysis.…”

Section: Resultsmentioning

confidence: 99%

“…The reaction was controlled by TLC. The solid formed was separated from the solvent by filtration and washed with petroleum ether [29,30] …”

Section: Methodsmentioning

confidence: 99%

“…The solid formed was separated from the solvent by filtration and washed with petroleum ether. [29,30] [1] [2] (S)-(+)-1-(1-(4-bromophenyl)ethyl)-3-(naphthalen-1-yl)thiourea: [3] Light yellow solid; yield 77 %; m.p. : 165-167 (R)-(À )-1-(1-(4-bromophenyl)ethyl)-3-(naphthalen-1-yl)thiourea: [4] Brown solid; yield 75 %; m.p.…”

Section: Synthesis Of 13-thiazolidine-45-dione Derivatives (17-32)mentioning

confidence: 99%

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Design, in Silico Studies and Biological Evaluation of New Chiral Thiourea and 1,3‐Thiazolidine‐4,5‐dione Derivatives

Evyapan,

Oruç‐Emre,

Sıcak

et al. 2023

Chemistry & Biodiversity

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In this study, new chiral thiourea and 1,3‐thiazolidine‐4,5‐dione derivatives were synthesized, it was aimed to evaluate the various biological activities and molecular docking of these compounds. Firstly, the new thioureas (1–16) were obtained by reacting 1‐naphthylisothiocyanate with different chiral amines. Then, the chiral thioureas were cyclized with oxalyl chloride to obtain 1,3‐thiazolidine‐4,5‐dione derivatives (17–32). All compounds were evaluated with several in vitro antioxidant and enzyme inhibition activities. Compound 30 was the most active compound against AChE, with a value of IC50=8.09±0.58 μM. On the other hand, all compounds were tested in silico absorption, distribution, metabolism, and excretion (ADME) assays to better understand their bioavailability. These physicochemical properties, pharmacokinetics, and drug‐likeness of all compounds were calculated using SwissADME. Furthermore, according to molecular docking analyses compound 30 exhibited significant binding affinities for all enzymes. Based on our overall observations, compound 30 could be recommended as a potential lead for the therapuetic of Alzheimer's.

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“…This has increased interest in such compounds in the pharmaceutical studies. According to the substituents they contain, thioureas show various biological activities i.e., anti-HIV, antituberculosis, anticancer, antimalarial, anticonvulsant, anticholinesterase, antityrosinase and antiurease [7,[12][13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Predictions of Drug-Likeness and Pharmacokinetic Properties of Some Chiral Thioureas as Potent Enzyme Inhibition Agents

2021

Turk J Chem

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A series of chiral thioureas (1-17) were synthesized from and tested for their anticholinesterase, tyrosinase and urease enzyme inhibitor activities. Various phenylisothiocyanates were added to solution of ʟ-cysteine in methanol:water (1:1 v/v) at room temperature and stirred for 24h. Precipitated solid was recrystallized from nbutanol. Pure compounds were characterized by NMR ( 1 H and 13 C), FTIR and CHNS. Tertiary amine containing N-(4-(diethylamino)phenyl)-N'-(2-mercapto-1carboxyethanyl)thiourea 17, N-(4-(dimethylamino)phenyl)-N'-(2-mercapto-1carboxyethanyl)thiourea 16 and trimethoxy containing N-(3,4,5-trimethoxyphenyl)-N'-(2-mercapto-1-carboxyethanyl)thiourea 14 were more active than galantamine against AChE and BChE enzymes. In tyrosinase enzyme inhibition activity, compound 14, 10, 12, 6, 13, and 11 exhibited higher tyrosinase inhibitory activity showing IC50 values of 1.1±0.1, 1.5±0.3, 1.6±0.6, 1.9±0.5, 2.2±0.9 and 2.9±0.2 mM, respectively. In urease enzyme inhibition activity assay, 17 showed higher activity. This work demonstrates the pharmacological significance of chiral thiourea derivatives synthesized from ʟ-cysteine and showing their potential. There is a need to perform more in vitro and in vivo biological activities followed by clinical trials to bring such thiourea to the market.

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Design and Synthesis of Novel Thioureas Derived from 4‐(4‐Fluorophenoxy)aniline as Anticancer Agents

Cited by 6 publications

References 26 publications

Design and evaluation of biological activities of 1,3‐oxazolidinone derivatives bearing amide, sulfonamide, and thiourea moieties

Design and evaluation of biological activities of 1,3‐oxazolidinone derivatives bearing amide, sulfonamide, and thiourea moieties

Design, in Silico Studies and Biological Evaluation of New Chiral Thiourea and 1,3‐Thiazolidine‐4,5‐dione Derivatives

Synthesis, Predictions of Drug-Likeness and Pharmacokinetic Properties of Some Chiral Thioureas as Potent Enzyme Inhibition Agents

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