1H, 13C and 15N NMR of spiro acridines integrated with pyrrole scaffolds

Vilková, Mária; Šoral, Michal; Bečka, Michal; Potočňák, Ivan; Sabolová, Danica; Béres, Tibor; Dušek, Michal; Imrich, Ján

doi:10.1002/mrc.4974

Cited by 3 publications

(1 citation statement)

References 20 publications

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“…In accordance with our previous results [23], the dihydroacridine moiety in 6a is nearly planar. On the other hand, in a related 1-[(E)-[(4 -bromophenyl)methylidene]amino]-5-oxo-1,5-dihydro-10 H-spiro[acridine-9 ,2-pyrrole]-4-carbonitrile compound [31], the dihydroacridine moiety is slightly parabolically curved as was also observed in some structures of dihydroacridines [32]. The mean plane of the dihydroacridine moiety in 6a is in a nearly orthogonal position towards the pyrrole ring (87.52(4) • ), partially due to the steric repulsion between the two mentioned systems and partially due to the sp 3 hybridized C2 atom that is shared by both systems and links them.…”

Section: X-ray Analysismentioning

confidence: 99%

Derivatives Incorporating Acridine, Pyrrole, and Thiazolidine Rings as Promising Antitumor Agents

Garberová,

Potočňák,

Tvrdoňová

et al. 2023

Molecules

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Derivatives combining acridine, pyrrole, and thiazolidine rings have emerged as promising candidates in the field of antitumor drug discovery. This paper aims to highlight the importance of these three structural motifs in developing potent and selective anticancer agents. The integration of these rings within a single molecule offers the potential for synergistic effects, targeting multiple pathways involved in tumor growth and progression. Spiro derivatives were efficiently synthesized in a two-step process starting from isothiocyanates and 2-cyanoacetohydrazide. The thiourea side chain in spiro derivatives was utilized as a key component for the construction of the thiazolidine-4-one ring through regioselective reactions with bifunctional reagents, namely methyl-bromoacetate, dietyl-acetylenedicarboxylate, ethyl-2-bromopropionate, and ethyl-2-bromovalerate. These reactions resulted in the formation of a single regioisomeric product for each derivative. Advanced spectroscopic techniques, including 1D and 2D NMR, FT-IR, HRMS, and single-crystal analysis, were employed to meticulously characterize the chemical structures of the synthesized derivatives. Furthermore, the influence of these derivatives on the metabolic activity of various cancer cell lines was assessed, with IC50 values determined via MTT assays. Notably, derivatives containing ester functional groups exhibited exceptional activity against all tested cancer cell lines, boasting IC50 values below 10 μM. Particularly striking were the spiro derivatives with methoxy groups at position 3 and nitro groups at position 4 of the phenyl ring. These compounds displayed remarkable selectivity and exhibited heightened activity against HCT-116 and Jurkat cell lines. Additionally, 4-oxo-1,3-thiazolidin-2-ylidene derivatives demonstrated a significant activity against MCF-7 and HCT-116 cancer cell lines.

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Section: X-ray Analysismentioning

confidence: 99%

Derivatives Incorporating Acridine, Pyrrole, and Thiazolidine Rings as Promising Antitumor Agents

Garberová,

Potočňák,

Tvrdoňová

et al. 2023

Molecules

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Synthesis, characterization, and antimicrobial evaluation of some novel anthracene heterocycles derivatives

Dardeer

Taha

Elamary

2020

Journal of Heterocyclic Chem

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A series of novel heterocyclic compounds containing anthracene moiety was synthesized. Reaction of (11R,15S)‐9,10‐dihydro‐9,10‐[3,4]furanoanthracene‐12,14‐dione with 2‐cyanoacetohydrazide gave 2‐cyano‐pyrroloanthracen acetamide (1), which acts as an adaptable material for the synthesis of new heterocyclic compounds. The synthesized compounds were examined for their antimicrobial activity against Escherichia coli and Staphylococcus aureus via p‐iodonitrotetrazolium violet formazon assay. The results exhibited great activity against the tested strains with a minimum bactericidal concentration range from 0.636 to 3.8 mg/mL) and 0.159 to 3.6 mg/mL for E coli and S aureus, respectively. Interestingly, the highest activity was recorded for chromene derivative (6) against both strains.

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Spectral, structural, and pharmacological studies of perillaldehyde and myrtenal based benzohydrazides

Garberová

Potočňák

Tvrdoňová

et al. 2023

Journal of Molecular Structure

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¹H, ¹³C and ¹⁵N NMR of spiro acridines integrated with pyrrole scaffolds

Cited by 3 publications

References 20 publications

Derivatives Incorporating Acridine, Pyrrole, and Thiazolidine Rings as Promising Antitumor Agents

Derivatives Incorporating Acridine, Pyrrole, and Thiazolidine Rings as Promising Antitumor Agents

Synthesis, characterization, and antimicrobial evaluation of some novel anthracene heterocycles derivatives

Spectral, structural, and pharmacological studies of perillaldehyde and myrtenal based benzohydrazides

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