Synthesis of New Planar-Chiral Linked [2.2]Paracyclophanes-N-([2.2]-Paracyclophanylcarbamoyl)-4-([2.2]Paracyclophanylcarboxamide, [2.2]Paracyclophanyl-Substituted Triazolthiones and -Substituted Oxadiazoles

Aly, Ashraf A.; Bräse, Stefan; Hassan, Alaa A.; Mohamed, Nasr K.; El-Haleem, Lamiaa E. Abd; Nieger, Martin

doi:10.3390/molecules25153315

Cited by 3 publications

(3 citation statements)

References 71 publications

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“…Crude products were purified by flash chromatography with silica gel 60 (0.040 × 0.063 mm, Geduran ® ) (Merck, Darmstadt, Germany). Compounds 2 and 5-8 were prepared according to the methodology mentioned in References [30] and [31], respectively.…”

Section: Methodsmentioning

confidence: 99%

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New Paracyclophanylthiazoles with Anti-Leukemia Activity: Design, Synthesis, Molecular Docking, and Mechanistic Studies

et al. 2020

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A new series of methyl 2-(2-(4′-[2.2]paracyclophanyl)-hydrazinylidene)-3-substituted-4-oxothiazolidin-5-ylidene)acetates 3a–f were synthesized from the reaction of paracyclophanyl-acylthiosemicarbazides 2a–f with dimethyl acetylenedicarboxylate. Based upon nuclear magnetic resonance (NMR), infrared (IR), and mass spectra (HRMS), the structure of the obtained products was elucidated. X-ray structure analysis was also used as unambiguous tool to elucidate the structure of the products. The target compounds 3a–f were screened against 60 cancer cell lines. They displayed anticancer activity against a leukemia subpanel, namely, RPMI-8226 and SR cell lines. The activity of compound 3a was found as the most cytotoxic potency against 60 cancer cell lines. Consequently, it was selected for further five doses analysis according to National Cancer Institute (NCI) protocol. The cytotoxic effect showed selectivity ratios ranging between 0.63 and 1.28 and between 0.58 and 5.89 at the GI50 and total growth inhibition (TGI) levels, respectively. Accordingly, compound 3a underwent further mechanistic study against the most sensitive leukemia RPMI-8226 and SR cell lines. It showed antiproliferation with IC50 = 1.61 ± 0.04 and 1.11 ± 0.03 µM against RPMI-8226 and SR cell lines, respectively. It also revealed a remarkable tubulin inhibitory activity, compared to colchicine with IC50 = 4.97 µM/mL. Caspase-3, BAX, and Bcl-2 assays for 3a using annexin V-FITC staining revealed significant pro-apoptotic activity. Furthermore, multidrug-resistant leukemia SR cells were used to show better resistance indices (1.285 ng/mL, 1.15-fold) than the reference. Docking studies with β-tubulin indicate that most of the tested compounds illustrated good binding at the colchicine binding site of the enzyme, especially for compound 3a, which made several interactions better than that of the reference colchicine.

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Section: Methodsmentioning

confidence: 99%

“…Starting with acyl hydrazide 1 [30], the acylthiosemicarbazides 2a-f could be prepared (Scheme 1). Compounds 2a-f were used as the target compounds for the formation of thiazolidinones, 3a,b,d-f, and 3c (Scheme 1).…”

Section: Chemistry Sectionmentioning

confidence: 99%

New Paracyclophanylthiazoles with Anti-Leukemia Activity: Design, Synthesis, Molecular Docking, and Mechanistic Studies

et al. 2020

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“…Previously, we reported the various classes of connection between PC and heterocycle moieties . Aly et al synthesized heterocycles conjugated to [2.2]paracyclophane such as five-membered rings (i.e., imidazolinone, pyrrole, triazolethiones, and substituted oxadiazoles) together with six-membered rings (i.e., pyridine). , …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

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The strategies of the syntheses of various (thio)ureas, semicarbazides, thiosemicarbazides, thiazolidones, and oxadiazole derived from the [2.2]paracyclophane molecule are achieved starting with 4-(2.2]paracyclophanyl)isocyanate. The structures of the obtained products were elucidated by NMR, mass spectrometry, and infrared (IR) spectroscopy in addition to high-resolution mass spectrometry (HRMS). X-ray structure analysis was also used to prove the assigned structure.

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Stereoselective synthesis of homochiral paracyclophanylindenofuranylimidazo[3.3.3]propellanes

et al. 2021

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The reaction between N-paracyclophanyl-substituted hydrazinecarbothioamides and dicyanomethylene-1,3-indanedione (CNIND), furnished planar and central chiral substituted (epiminomethanoimino)indenofuranyl)-1,4-(1,4-dibenzenocyclohexaphane)-1,2-carboxamides as a type of paracyclophanylfuroimidazo[3.3.3]propellanes in (35-81% yields) as a major product as single diastereomers, and substituted spiro[indene-2,4'-indeno-pyran]-3'-carbonitrile (9-12% yields) as a minor product. To prepare the homochiral paracyclophanylpropellane, oxidation of scalemic  Alaa A. Hassan

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Synthesis of New Planar-Chiral Linked [2.2]Paracyclophanes-N-([2.2]-Paracyclophanylcarbamoyl)-4-([2.2]Paracyclophanylcarboxamide, [2.2]Paracyclophanyl-Substituted Triazolthiones and -Substituted Oxadiazoles

Cited by 3 publications

References 71 publications

New Paracyclophanylthiazoles with Anti-Leukemia Activity: Design, Synthesis, Molecular Docking, and Mechanistic Studies

New Paracyclophanylthiazoles with Anti-Leukemia Activity: Design, Synthesis, Molecular Docking, and Mechanistic Studies

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

Stereoselective synthesis of homochiral paracyclophanylindenofuranylimidazo[3.3.3]propellanes

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