Efficient Synthesis of Various Substituted (Thio)Ureas, Semicarbazides, Thiosemicarbazides, Thiazolidones, and Oxadiazole Derived from [2.2]Paracyclophane

Alshammari, Mohammed B.; Aly, Ashraf A.; Bräse, Stefan; Nieger, Martin; El-Haleem, Lamiaa E. Abd

doi:10.1021/acsomega.2c00141

Cited by 3 publications

(2 citation statements)

References 28 publications

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“…We recently reacted thioureas bearing a [2.2]paracyclophane moiety with diethyl acetylene-dicarboxylate ( 4a ) to form thiazolidinones ( Alshammari et al, 2022 ). An X-ray crystal structure showed the C=N and C=C double bonds to both have ( Z ) stereochemistry ( Figure 5 ); in the current series 5a-l, we assign the C=N and C=C bonds as both ( Z ) by analogy with our earlier work.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of new thiazolidinone/uracil derivatives as antiproliferative agents targeting EGFR and/or BRAFV600E

et al. 2022

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Thiourea derivatives of uracil were efficiently synthesized via the reaction of 5-aminouracil with isothiocyanates. Then, we prepared uracil-containing thiazoles via condensation of thioureas with diethyl/dimethyl acetylenedicarboxylates. The structures of the products were confirmed by a combination of spectral techniques including infra-red (IR), nuclear magnetic resonance (NMR), mass spectrometry (MS) and elemental analyses. A rationale for the formation of the products is presented. The newly synthesized compounds were evaluated for their in vitro antiproliferative activity against four cancer cell lines. The compounds tested showed promising antiproliferative activity, with GI50 values ranging from 1.10 µM to 10.00 µM. Compounds 3c, 5b, 5c, 5h, 5i, and 5j were the most potent derivatives, with GI50 values ranging from 1.10 µM to 1.80 µM. Compound 5b showed potent inhibitory activity against EGFR and BRAFV600E with IC50 of 91 ± 07 and 93 ± 08 nM, respectively, indicating that this compound could serve as a dual inhibitor of EGFR and BRAFV600E with promising antiproliferative properties. Docking computations revealed the great potency of compounds 5b and 5j towards EGFR and BRAFV600E with docking scores of −8.3 and −9.7 kcal/mol and −8.2 and −9.3 kcal/mol, respectively.

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of new thiazolidinone/uracil derivatives as antiproliferative agents targeting EGFR and/or BRAFV600E

et al. 2022

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“…Recently, Aly et al reported that 2-(4′-[2.2]paracyclophanyl-4 H - N -substituted-hydrazine-carbothioamides 7a – f were prepared in 80–88% yields by refluxing compound 6 with the isothiocyanates in EtOH for 6–8 h ( Scheme 3 ) [ 52 ].…”

Section: Synthesis Of Thiosemicarbazide Derivativesmentioning

confidence: 99%

Transition Metal Complexes of Thiosemicarbazides, Thiocarbohydrazides, and Their Corresponding Carbazones with Cu(I), Cu(II), Co(II), Ni(II), Pd(II), and Ag(I)—A Review

et al. 2023

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: This review focuses on some interesting and recent applications of transition metals towards the complexation of thiosemicarbazides, thiocarbohydrazides, and their corresponding carbazones. We started the review with a description of the chosen five metals, including Cu[Cu(I), Cu(II], Co(II), Ni(II), Pd(II), and Ag(I) and their electronic configurations. The stability of the assigned complexes was also discussed. We shed light on different routes describing the synthesis of these ligands. We also reported on different examples of the synthesis of Cu(I), Cu(II), Co(II), Ni(II), Ag(I), and Pd(II) of thiosemicarbazide and thiocarbohydrazide complexes (until 2022). This review also deals with a summary of the fruitful use of metal complexes of thiosemicarbazones and thiocarbazones ligands in the field of catalysis. Finally, this recent review focuses on the applications of these complexes related to their biological importance.

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2-[2-(Phenylcarbamoyl)hydrazinylidene]propanoates: synthesis, structure and in vitro study of the activity against influenza virus

Pelipko,

Litvinov,

Sinegubova

et al. 2024

Mendeleev Communications

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Efficient Synthesis of Various Substituted (Thio)Ureas, Semicarbazides, Thiosemicarbazides, Thiazolidones, and Oxadiazole Derived from [2.2]Paracyclophane

Cited by 3 publications

References 28 publications

Design and synthesis of new thiazolidinone/uracil derivatives as antiproliferative agents targeting EGFR and/or BRAFV600E

Design and synthesis of new thiazolidinone/uracil derivatives as antiproliferative agents targeting EGFR and/or BRAFV600E

Transition Metal Complexes of Thiosemicarbazides, Thiocarbohydrazides, and Their Corresponding Carbazones with Cu(I), Cu(II), Co(II), Ni(II), Pd(II), and Ag(I)—A Review

2-[2-(Phenylcarbamoyl)hydrazinylidene]propanoates: synthesis, structure and in vitro study of the activity against influenza virus

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