NEW ROUTE FOR THE SYNTHESES OF SOME NOVEL DERIVATIVES OF 3-ARYL BENZO[d] THIAZOLE-2(3H)-IMINE FROM HIGH SUBSTITUTED THIOUREAS

Miar, Marzieh; Pourshamsian, Khalil; Shiroudi, Abolfazl; Hatamjafari, Farhad; Oliaey, Ahmad Reza

doi:10.4067/s0717-97072020000204853

Cited by 16 publications

(17 citation statements)

References 29 publications

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“…However, HFB derivatives ( Ia – b ) have a higher energy gap value indicating that DFBPs derivatives ( IIa – b ) have a greater capacity to transfer charge density from HOMO to LUMO, that is, IIa – b is softer than Ia – b . Additionally, a large energy gap increases the global hardness of compounds as follows: Ia > Ib > IIa > IIb , and their chemical reactivity decrease in the reverse order: Ia < Ib < IIa < IIb [32] (Table S3). These results show that all compounds exhibit a low energy gap, suggesting a significant intramolecular charge from HOMO to LUMO groups and high chemical reactivity [33,34] .…”

Section: Resultsmentioning

confidence: 99%

Cysteine‐Based Perfluorinated Derivatives: A Theoretical and Experimental Study**

et al. 2023

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Cysteine-based perfluoroaromatic (hexafluorobenzene (HFB) and decafluorobiphenyl (DFBP)) were synthesized and established as a chemoselective and available core to construct molecular systems ranging from small molecules to biomolecules with interesting properties. The DFBP was found more effective than HFB for the monoalkylation of decorated thiol molecules. As proof of concept of the potential application of perfluorinated derivatives as non-cleavable linkers, some antibody-perfluorinated conjugates were prepared via thiol through two different strategies, i) using thiol from reduced cystamine coupling to carboxylic acids from mAb by amide bond, and ii) using thiols from reduction of mAb disulfide bond. Conjugates cell binding analysis demonstrated that the bioconjugation does not affect the macromolecular entity. Besides, some molecular properties of synthesized compounds are evaluated through spectroscopic characterization (FTIR and 19 F NMR chemical shifts) and theoretical calculations. The comparison of calculated and experimental 19 F NMR shifts and IR wavenumbers give excellent correlations, asserting as powerful tools in structurally identifying HFB and DFBP derivatives. Moreover, molecular docking was also developed to predict cysteine-based perfluorated derivatives' affinity against topoisomerase Il and cyclooxygenase 2 (COX-2). The results suggested that mainly cysteine-based DFBP derivatives could be potential topoisomerase II α and COX-2 binders, becoming potential anticancer agents and candidates for anti-inflammatory treatment.

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Section: Resultsmentioning

confidence: 99%

Cysteine‐Based Perfluorinated Derivatives: A Theoretical and Experimental Study**

et al. 2023

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“…DFT computations were done with Gaussian 09 [71] . The geometry of compounds 4 b‐1 , 4 b‐2 , 4 a‐7 , and 4 b‐4 was optimized by using the DFT method with B3LYP in the ground state [72] . LANL2DZ was chosen as the basis set [73] .…”

Section: Methodsmentioning

confidence: 99%

“…[71] The geometry of compounds 4 b-1, 4 b-2, 4 a-7, and 4 b-4 was optimized by using the DFT method with B3LYP in the ground state. [72] LANL2DZ was chosen as the basis set. [73] Thereafter, the energy of compounds 4 b-1, 4 b-2, 4 a-7, and 4 b-4 was computed by keeping the DFT setups at the same level.…”

Section: Dft Calculationsmentioning

confidence: 99%

Synthesis, DFT Calculations, and Molecular Docking Study of Acetohydrazide‐Based Sulfonamide Derivatives as Paraoxonase 1 Inhibitors

Arslan¹,

Gökçe²,

Muhammed³

et al. 2023

ChemistrySelect

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Paraoxonase 1 (PON1), an esterase linked to high-density lipoprotein (HDL), is known to have strong antioxidant and anti-cardiovascular properties. In this study, eleven acetohydrazide-based sulfonamide derivatives were synthesized. All compounds were characterized by appropriate spectroscopic techniques and elemental analyses. To better understand the inhibitory properties of the new sulfonamide derivatives, their in vitro effects on purified PON1 enzyme activity were studied. For this purpose, PON1 was purified from human serum using simple chromatographic methods. In the experimental study, the novel compounds were found to be potent inhibitors of paraoxonase 1. The mode of binding to the enzyme, for the relatively active compounds, was investigated through molecular docking. The most active compound N'-(naphthalen-2ylsulfonyl)-2-(2-oxo-1,3-benzothiazol-3(2H)-yl)acetohydrazide demonstrated the highest interaction with the enzyme. Furthermore, the electrochemical properties of these compounds were assessed through DFT (density functional theory) analysis. N'-(naphthalen-2-ylsulfonyl)-2-(2-oxo-1,3-benzothiazol-3(2H)-yl)acetohydrazide is anticipated to have the highest potential to take part in electron exchanges whereas N'-[(4fluorophenyl)sulfonyl]-2-(2-oxo-1,3-benzoxazol-3(2H)yl)acetohydrazide is expected to have the highest chemical stability.

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“…The electronic chemical potential is represented by µ, where the compounds with larger chemical potential values are more reactive than those with small electronic chemical potentials [16]. From Table 3, we have noticed that all chemical potential (µ) values of complex ASA/HPCD are negative for all models in gas and solvation.…”

Section: Homo-lumo Parametersmentioning

confidence: 99%

Theoretical Study of Complex Aspirin and Hydroxypropyl-β-cyclodextrin in Solvent Phase

Jayyinunnisya

Solihat

Sugimori

et al. 2022

J. Phys.: Conf. Ser.

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We estimate the configuration of complex ASA/HPCD in the gas phase by using PM3 and B3LYP methods. Some physical properties in the gas phase, such as complexation energy, deformation energy, dipole moment, etc., are calculated by using PM3 and B3LYP methods. We investigate the dependence of physical properties such as complexation energy, etc., on solvation by using PM3 and B3LYP methods with the PCM method. Complex ASA/HPCD becomes more stable than the dissociation state. The present results suggest that the effect of solvent can be increasing the energy complexation, LUMO energy, HOMO energy, HOMO-LUMO gap energy, electronic potential, and chemical hardness, whereas the electrophilicity decrease.

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NEW ROUTE FOR THE SYNTHESES OF SOME NOVEL DERIVATIVES OF 3-ARYL BENZO[d] THIAZOLE-2(3H)-IMINE FROM HIGH SUBSTITUTED THIOUREAS

Cited by 16 publications

References 29 publications

Cysteine‐Based Perfluorinated Derivatives: A Theoretical and Experimental Study**

Cysteine‐Based Perfluorinated Derivatives: A Theoretical and Experimental Study**

Synthesis, DFT Calculations, and Molecular Docking Study of Acetohydrazide‐Based Sulfonamide Derivatives as Paraoxonase 1 Inhibitors

Theoretical Study of Complex Aspirin and Hydroxypropyl-β-cyclodextrin in Solvent Phase

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