Synthesis, Characterization, and Anticancer Activity (MCF‐7) of Some Acetanilide‐based Heterocycles

Abdel‐Latif, Ehab; Keshk, Eman M.; Khalil, A. M.; Saeed, Ali; Metwally, Heba M.

doi:10.1002/jhet.3294

Cited by 13 publications

(4 citation statements)

References 29 publications

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“…Fortunately, a single product, N ‐(4‐anisyl)‐5‐imino‐6‐methyl‐3‐oxo‐3,5‐dihydro‐2 H ‐thiazolo[3,2‐ a ]thieno‐[2,3‐ d ]pyrimidine‐7‐carboxamide ( 18 ), has been produced (Scheme 3). We expect the reaction to proceed via nucleophilic substituting the chlorine atom from compound 3 , followed by intramolecular cyclization of the thiocyanate intermediate and Dimroth‐like rearrangements [33, 34] to generate the 2‐(thienylimino)thiazolidin‐4‐one intermediate 17 . The unexpected ring closure of the intermediate 17 through nucleophilic addition of the imino group (=NH‐) on the nitrile group resulted in the formation of thiazolo[3,2‐ a ]thiazolo[2,3‐ d ]pyrimidine ring system 18 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and anticancer activity of some thiophene, thienyl‐thiazole, and thienyl‐benzofuran analogues

El-Rayyes

Almatari

Ghani

et al. 2023

Journal of Heterocyclic Chem

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N‐(Anisyl)‐5‐(2‐chloroacetamido)‐4‐cyano‐3‐methylthiophene‐2‐carboxamide (3) was synthesized and reacted with several nucleophilic reagents. The reactions with sulfur nucleophiles (namely, mercaptoacetic acid, ethyl 2‐mercaptoacetate, 5‐(phenylamino)‐1,3,4‐thiadiazole‐2‐thiol, 2‐mercapto‐4,6‐dimethyl‐nicotinonitrile, 4‐anilino‐3‐arylazo‐4‐mercapto‐butenones, ethyl 3‐anilino‐2‐arylazo‐3‐mercapto‐acrylates, and ammonium thiocyanate) yielded the corresponding sulfide, thiophene, or thiazolin‐4‐one derivatives, respectively. The reaction with salicylaldehyde (an example of oxygen nucleophile) furnished the targeting benzofuran compound 21. The reactions with nitrogen nucleophiles (namely, piperidine and aniline) yielded the corresponding thiophene‐carboxamide derivatives 23 and 25, respectively. IR, 1H NMR, and 13C NMR were used to deduce the structures of the target thiophene containing compounds. The effect of the synthesized thiophenes on the viability of HepG2, A2780, and A2780CP was determined. The most effective drug was shown by the thienopyridine‐carboxamide compound 11, against liver cancer cell lines (HepG2) and ovarian cancer cell lines (A2780CP and A2780), whose IC50 values were remarkably near those of Sorafenib, the antitumor drug.

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Section: Resultsmentioning

confidence: 99%

“…Four (18), has been produced (Scheme 3). We expect the reaction to proceed via nucleophilic substituting the chlorine atom from compound 3, followed by intramolecular cyclization of the thiocyanate intermediate and Dimroth-like rearrangements [33,34]…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and anticancer activity of some thiophene, thienyl‐thiazole, and thienyl‐benzofuran analogues

El-Rayyes

Almatari

Ghani

et al. 2023

Journal of Heterocyclic Chem

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“…As a part of our continuous research program on the chemistry of N-aryl-2-chloroacetamide compounds [23][24][25], herein we report on the chemical reactivity of 2-chloroacetamide reagents towards the highly versatile sulfur donner, ammonium thiocyanate. The heterocyclization of Naryl-2-chloroacetamide derivatives 1 upon treatment with ammonium thiocyanate has been achieved by refluxing in ethanol for 4 hours to generate the corresponding 2-(arylimino) thiazolidin-4-ones 2a-e (Scheme 1).…”

Section: Synthesis Of 2-(arylimino)thiazolidin-4-onesmentioning

confidence: 99%

Molecular geometry and biological activity of 2-(4-substituted-phenylimino)thiazolidin- 4-one compounds

El-Rayyes,

T. Mogharbel,

H. Abdel-Rhman

et al. 2023

Bull. Chem. Soc. Eth.

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ABSTRACT. A series of 2-(4-substituted-phenylimino)thiazolidin-4-one compounds was synthesized via heterocyclizing the corresponding N-aryl-2-chloroacetamides with ammonium thiocyanate. Their chemical structures were elucidated based on an extensive analysis of their spectroscopic data, including infrared, 1H NMR, 13C NMR, and mass analyses. The possible tautomeric forms of synthesized thiazolidine-4-ones were studied. The tautomerization equilibrium parameters, ΔH, ΔG, and Keq were calculated using the DFT/B3LYP methodology, where it has been indicated that the tautomeric form, phenylimino, is more favourable than the phenylamino form. The antibacterial and antioxidant properties of the synthesized thiazolidin-4-ones were investigated. 2-(Chlorophenyl-imino)thiazolidin-4-one displayed potent antibacterial activity against E. coli (88.46%) and S. aureus (91.66%), and highest percent of inhibition (81.8%, ABTS assay). KEY WORDS: N-aryl-2-chloroacetamides, Ammonium thiocyanate, 2-(Arylimino)thiazolidin-4-ones, Mulliken’s charges, Dipole moment, ABTS assay Bull. Chem. Soc. Ethiop. 2023, 37(5), 1275-1286. DOI: https://dx.doi.org/10.4314/bcse.v37i5.18

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“…Several studies have been carried out using various sulfur and/ or nitrogen-containing heterocyclic compounds, including thiophene, thiazole, and pyridine, directed towards different pathologies. These thiophene, thiazole, and pyridine-containing compounds show anticancer [4][5][6][7][8], anti-inflammatory [9][10][11], antibacterial [12][13][14], antioxidant [15], anti-oxidant [16], anti-fungal [17,18], anti-coronavirus [19,20] properties. Thiazoles were also found to act as anti-Alzheimer [21], anti-tubercular [22], and anti-diabetic [23].…”

Section: Introductionmentioning

confidence: 99%

New thiazole, thiophene and 2-pyridone compounds incorporating dimethylaniline moiety: synthesis, cytotoxicity, ADME and molecular docking studies

Metwally,

Younis,

Abdel-Latif

et al. 2024

BMC Chemistry

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Various sets of thiazole, thiophene, and 2-pyridone ring structures containing a dimethylaniline component were synthesized. Substituted thiazoles 2–3 and thiophenes 5–7 were produced by reacting thiocarbamoyl compound 4 with α-halogenated reagents in different basic conditions. Also, a series of 2-pyridone derivatives 9a–f substituted with dimethylaniline was synthesized through Michael addition of malononitrile to α,β-unsaturated nitrile derivatives 8a–f. The synthesized products were structurally proven by spectroscopic methods such as IR, 1H NMR, 13C NMR, and MS data. Furthermore, the anti-cancer efficacy of the compounds was assessed using the MTT assay on two cell lines: hepatocellular carcinoma (HepG-2) and breast cancer (MDA-MB-231). The results showed the highest growth inhibition for derivatives 2, 6, 7, and 9c, which were further examined for their IC50 values. The IC50 for compound 2 showed equipotent activity (IC50 = 1.2 µM) against the HepG-2 cell line compared to Doxorubicin (IC50 = 1.1 µM). Compounds 2, 6, 7 and 9c showed very good ADME assessments for further drug administration. Moreover, the PASS theoretical prediction for the compounds showed high antimitotic and antineoplastic activities for compounds 2, 6, 7, and 9c, as well as potent inhibition activity for the insulysin enzyme (IDE). Molecular docking stimulations were performed on CDK1/CyclinB1/CKS2 (PDB ID: 4y72) and BPTI (PDB ID: 2ra3). When docked into (PDB ID: 4y72), all of the tested compounds showed considerable inhibition, and the 2-pyridone derivative 9d had the maximum binding affinity (− 8.1223 kcal/mol). While thiophene derivative 6 offered the maximum binding affinity (− 7.5094 kcal/mol) when docked into (PDB ID: 2ra3). Graphical Abstract

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Synthesis, Characterization, and Anticancer Activity (MCF‐7) of Some Acetanilide‐based Heterocycles

Cited by 13 publications

References 29 publications

Synthesis and anticancer activity of some thiophene, thienyl‐thiazole, and thienyl‐benzofuran analogues

Synthesis and anticancer activity of some thiophene, thienyl‐thiazole, and thienyl‐benzofuran analogues

Molecular geometry and biological activity of 2-(4-substituted-phenylimino)thiazolidin- 4-one compounds

New thiazole, thiophene and 2-pyridone compounds incorporating dimethylaniline moiety: synthesis, cytotoxicity, ADME and molecular docking studies

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