Recent Advances in Chemistry of Condensed 4‐Thiazolidinones

Gupta, Richa

doi:10.1002/jhet.2476

Cited by 5 publications

(1 citation statement)

References 40 publications

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“…During the last few decades, they have attracted attention due to their proven usefulness in material sciences. [1][2][3] Moreover, the study of heterocyclic compounds is also of great interest theoretically. Specifically, thiazolidinones which belong to an important group of heterocyclic compounds, have been widely explored for their application in the field of medicine.…”

Section: Introductionmentioning

confidence: 99%

Molecular Structure, FT-IR, NMR (13C/1H), UV-Vis Spectroscopy and DFT Calculations on (2Z, 5Z)-3-N(4-Methoxy phenyl)-2-N'(4-methoxy phenyl imino)-5-((E)-3-(2-nitrophenyl)allylidene) thiazolidin-4-one

Rahmani¹,

Djafri²,

Chouaih³

et al. 2019

S.Afr.j.chem.

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In this study, some molecular properties of (2Z, 5Z)-3-N(4-methoxy phenyl)-2-N'(4-methoxy phenyl imino)-5-((E)-3-(2-nitrophenyl) allylidene) thiazolidin-4-one (MNTZ) are evaluated using a combination of spectroscopic characterization (FT-IR, 1 H and 13 C NMR chemical shifts) and theoretical calculations. Molecular geometry, vibrational wavenumbers, gauge-independent atomic orbital (GIAO), 1 H and 13 C chemical shift values and NBO analysis are investigated using B3LYP and PBE functionals with the 6-31G(d,p) basis set in the ground state. The calculated geometrical parameters and vibrational spectra are compared to available experimental data and each vibrational frequency is assigned on the basis of potential energy distribution (PED). The electronic transitions are calculated using time-dependent density functional theory (TDDFT). The energy band gap between the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies are obtained by computing the frontier molecular orbitals using the B3LYP/6-31G(d,p) and PBE/6-31G(d,p) levels along with the global reactivity descriptors. Mulliken atomic charges and molecular electrostatic potential (MEP) are simulated using both functionals to find more reactive sites for electrophilic and nucleophilic attack. Finally, the thermodynamic functions (heat capacity, entropy, and enthalpy) from spectroscopic data are obtained and discussed in the range of 100-1000 K.

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Section: Introductionmentioning

confidence: 99%

Molecular Structure, FT-IR, NMR (13C/1H), UV-Vis Spectroscopy and DFT Calculations on (2Z, 5Z)-3-N(4-Methoxy phenyl)-2-N'(4-methoxy phenyl imino)-5-((E)-3-(2-nitrophenyl)allylidene) thiazolidin-4-one

Rahmani¹,

Djafri²,

Chouaih³

et al. 2019

S.Afr.j.chem.

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The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones

et al. 2018

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A series of tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7(1H, 6H)-diones were synthesized via the reaction of imidazotriazinethiones and bromoacetic acid followed by condensation with isatins. Amidine skeletal rearrangement of 3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7 (1H, 6H)-diones into 1,3a,4,9a-tetrahydroimidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-2,8 (3H, 7H)-diones under KOH treatment has been studied. The influence of substituents at positions 1,3,3a,6,9a of imidazothiazolotriazine on the ability to undergo rearrangement was analyzed based on experimental data and theoretical calculations. Both imidazothiazolo[3,2-b]triazines and their rearrangement products were evaluated for their cytotoxic activity against rhabdomyosarcoma, A549, HCT116 and MCF7 human cancer cell lines by MTT assay. Among the derivatives, 1,3-diethyl-6-[1-(2-propyl)-2-oxoindolin-3-ylidene]-3,3a,9,9a-tetrahydroimidazo [4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7(1H, 6H)-dione 4i was found to have the highest antiproliferative activity toward the tested cell lines (4i: [Formula: see text], 2.29, 0.47 and [Formula: see text], respectively). The [Formula: see text] value of compound 4i against normal human embryonic kidney cells HEK293 was [Formula: see text], which appeared to be 6-41-fold higher than [Formula: see text] values of 4i against human cancer cells.

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The Literature of Heterocyclic Chemistry, Part XVI, 2016

Беленький

Evdokimenkova

2018

Advances in Heterocyclic Chemistry

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Recent Advances in Chemistry of Condensed 4‐Thiazolidinones

Cited by 5 publications

References 40 publications

Molecular Structure, FT-IR, NMR (13C/1H), UV-Vis Spectroscopy and DFT Calculations on (2Z, 5Z)-3-N(4-Methoxy phenyl)-2-N'(4-methoxy phenyl imino)-5-((E)-3-(2-nitrophenyl)allylidene) thiazolidin-4-one

Molecular Structure, FT-IR, NMR (13C/1H), UV-Vis Spectroscopy and DFT Calculations on (2Z, 5Z)-3-N(4-Methoxy phenyl)-2-N'(4-methoxy phenyl imino)-5-((E)-3-(2-nitrophenyl)allylidene) thiazolidin-4-one

The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones

The Literature of Heterocyclic Chemistry, Part XVI, 2016

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