Conformations, equilibrium thermodynamics and rotational barriers of secondary thiobenzanilides

Kozic, Ján; Novák, Zdeněk; Římal, Václav; Profant, Václav; Kuneš, Jiřı́; Vinšová, Jarmila

doi:10.1016/j.tet.2016.02.035

Cited by 8 publications

(3 citation statements)

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“…These results suggest that thioamides with a strongly polarized nitro group in the ortho position of the acyl moiety are more prone to be stabilized in the more stable rotamer in polar solvents. This is in accordance with results obtained by J. Kozic et al [ 30 ]. Indeed, these authors found, for a 2-methoxybenzothioamide derivative, that the ( Z )/( E ) rotamer ratio ranged from 97:3 in (CD 3 ) 2 CO to 86:14 in DMSO- d 6 , despite having not found any apparent relationship between the solvents’ properties and the ( Z )/( E ) conformational ratio.…”

Section: Resultssupporting

confidence: 94%

Synthesis and the In Vitro Evaluation of Antitumor Activity of Novel Thiobenzanilides

et al. 2023

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Cancer is a generic term for a large group of diseases that are the second-leading cause of death worldwide, accounting for nearly 10 million deaths in 2020. Melanoma is a highly aggressive skin tumor with an increasing incidence and poor prognosis in the metastatic stage. Breast cancer still stands as one of the major cancer-associated deaths among women, and diagnosed cases are increasing year after year worldwide. Despite the recent therapeutic advances for this type of cancer, novel drugs and treatment strategies are still urgently needed. In this paper, the synthesis of 18 thiobenzanilide derivatives (17 of them new) is described, and their cytotoxic potential against melanoma cells (A375) and hormone-dependent breast cancer (MCF-7) cells is evaluated using the MTT assay. In the A375 cell line, most of the tested thiobenzanilides derivatives showed EC50 values in the order of μM. Compound 17 was the most promising, with an EC50 (24 h) of 11.8 μM. Compounds 8 and 9 are also interesting compounds that deserve to be further improved. The MCF-7 cell line, on the other hand, was seen to be less susceptible to these thiobenzanilides indicating that these compounds show different selectivity towards skin and breast cancer cells. Compound 15 showed the highest cytotoxic potential for MCF-7 cells, with an EC50 (24 h) of 43 μM, a value within the range of the EC50 value determined for tamoxifen (30.0 μM). ADME predictions confirm the potential of the best compounds. Overall, this work discloses a new set of thiobenzanilides that are worth being considered as new scaffolds for the further development of anticancer agents.

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Section: Resultssupporting

confidence: 94%

Synthesis and the In Vitro Evaluation of Antitumor Activity of Novel Thiobenzanilides

et al. 2023

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“…Analytical solutions [1][2][3]33 for spectral lineshape have been used for fitting of the two-state exchange, but only numerical methods 4-6, 29, 30, 34 have been applied in the case of systems containing more states than two. This section illustrates the use and benefits of the analytical treatment of the multi-state chemical exchange scheme containing fast exchange processes (see Sec.…”

Section: Analysis Of An Actual System Exhibiting Multi-state Exchangementioning

confidence: 99%

“…NMR lineshape fitting is a straightforward method to obtain transition rate coefficients and often requires only the acquisition of simple 1D NMR spectra. [1][2][3] For more complicated molecules (e.g., proteins) HSQC spectra can be analyzed, where either a 1D crosssection [4][5][6] or the full 2D spectrum [7][8][9] lineshape is fitted. NMR lineshape fitting procedure is most suitable for the analysis of exchange processes with transition rate coefficients approximately in the range of 10-10 5 s −1 .…”

Section: Introductionmentioning

confidence: 99%

NMR Lineshape Analysis: Analytical Solution of Multi-State Chemical Exchange with Applications to Kinetics of Host-Guest Systems

Březina

Hanyková

Velychkivska

et al. 2022

Preprint

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Nuclear magnetic resonance (NMR) lineshape analysis is a powerful tool for the study of chemical kinetics. Here we provide techniques for analysis of the relationship between experimentally observed spin kinetics and corresponding chemical kinetics. The advantages of using analytical solutions for two-, three- or generally N-state exchange lineshapes (without J-coupling) over the widely used numerical calculation for NMR spectral fitting are demonstrated. Several aspects of exchange kinetics including the generalization of coalescence conditions in two-state exchange, the possibility of multiple processes between two states and differences between equilibrium and steady-state modes are discussed. ‘Reduced equivalent schemes’ are introduced for spin kinetics containing fast-exchanging states, effectively reducing the number of exchanging states. The theoretical results have been used to analyze a host-guest system containing an oxoporphyrinogen complexed with camphorsulfonic acid and several other literature examples, including isomerization, protein kinetics, or enzymatic reactions. The theoretical treatment and experimental examples present an expansion of the systematic approach to rigorous analyses of systems with rich chemical kinetics through NMR lineshape analysis.

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Thioamides: Overview

Murai¹

2019

Chemistry of Thioamides

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Conformations, equilibrium thermodynamics and rotational barriers of secondary thiobenzanilides

Cited by 8 publications

References 24 publications

Synthesis and the In Vitro Evaluation of Antitumor Activity of Novel Thiobenzanilides

Synthesis and the In Vitro Evaluation of Antitumor Activity of Novel Thiobenzanilides

NMR Lineshape Analysis: Analytical Solution of Multi-State Chemical Exchange with Applications to Kinetics of Host-Guest Systems

Thioamides: Overview

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