Synthesis of difluorinated β-ketosulfones and novel gem-difluoromethylsulfone-containing heterocycles as fluorinated building blocks

Loghmani-Khouzani, Hossein; Hajiheidari, Dariush

doi:10.1016/j.jfluchem.2009.12.022

Cited by 25 publications

(8 citation statements)

References 77 publications

(14 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…White crystals (yield 90%), m.p. 179–181 °C (reported: 189–191 °C [ 40 ]); IR (KBr, ν cm −1 ): 3410 (NH) and 1675 (C=O); 1 H-NMR (DMSO- d 6 ) δ ppm: 5.04 (s, 2H, CH 2 ), 7.09–7.13 (m, 2H, H-5 and H-6 of 2-mercaptobenzimidazole), 7.40–7.42 (m, 2H, H-4 and H-7 of 2-mercaptobenzimidazole), 7.64 (d, 2H, H-3 and H-5 of 4-ClC 6 H 4 , J = 8.0 Hz), 8.08 (d, 2H, H-2 and H-6 of 4-ClC 6 H 4 , J = 8.5 Hz), 12.64 (s, 1H, NH); 13 C-NMR (DMSO- d 6 ) δ ppm: 40.49 (CH 2 ), 112.45, 121.87, 129.41, 130.82, 134.67, 139.06, 149.82, 193.09 (C=O); ESI MS m / z : 302.9 [M] + , 304.9 [M + 2] + .…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Crystal Study, and Anti-Proliferative Activity of Some 2-Benzimidazolylthioacetophenones towards Triple-Negative Breast Cancer MDA-MB-468 Cells as Apoptosis-Inducing Agents

Abdel‐Aziz

Eldehna

Ghabbour

et al. 2016

IJMS

View full text Add to dashboard Cite

On account of its poor prognosis and deficiency of therapeutic stratifications, triple negative breast cancer continues to form the causative platform of an incommensurate number of breast cancer deaths. Aiming at the development of potent anticancer agents as a continuum of our previous efforts, a novel series of 2-((benzimidazol-2-yl)thio)-1-arylethan-1-ones 5a–w was synthesized and evaluated for its anti-proliferative activity towards triple negative breast cancer (TNBC) MDA-MB-468 cells. Compound 5k was the most active analog against MDA-MB-468 (IC50 = 19.90 ± 1.37 µM), with 2.1-fold increased activity compared to 5-fluorouracil (IC50 = 41.26 ± 3.77 µM). Compound 5k was able to induce apoptosis in MDA-MB-468, as evidenced by the marked boosting in the percentage of florecsein isothiocyanate annexin V (Annexin V–FITC)-positive apoptotic cells (upper right (UR) + lower right (LR)) by 2.8-fold in comparison to control accompanied by significant increase in the proportion of cells at pre-G1 (the first gap phase) by 8.13-fold in the cell-cycle analysis. Moreover, a quantitative structure activity relationship (QSAR) model was established to investigate the structural requirements orchestrating the anti-proliferative activity. Finally, we established a theoretical kinetic study.

show abstract

Section: Methodsmentioning

confidence: 99%

Synthesis, Crystal Study, and Anti-Proliferative Activity of Some 2-Benzimidazolylthioacetophenones towards Triple-Negative Breast Cancer MDA-MB-468 Cells as Apoptosis-Inducing Agents

Abdel‐Aziz

Eldehna

Ghabbour

et al. 2016

IJMS

View full text Add to dashboard Cite

show abstract

“…[21] In the second step, obtained 1,3benzo[d]oxazole-2-thiol (1) was reacted with different kinds of acetophenone derivatives in the presence of sodium ethoxide through conventional and microwave techniques with high yields to obtain 2-(benzo[d]oxazol-2-ylthio)-1-(4-substitutedphenyl)ethan-1-one (2 a-d). [22,23] When compounds 2 a-d were reacted with hydroxylammonium chloride, and sodium acetate, 2-( benzo[d]oxazol-2-ylthio)-1-(4-substitutedphenyl)ethan-1one oxime (3 a-d) were obtained through conventional and microwave techniques with high yields (up to 91 %) (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Molecular Docking Studies of Potent Urease Inhibitors Based on Benzoxazole Scaffold

et al. 2021

View full text Add to dashboard Cite

In this study, we report the synthesis, in silico molecular docking, and in vitro urease inhibition studies of a novel series of benzoxazole derivatives. The title compound in the series namely (2-(benzo[d]oxazol-2-ylthio)-1-(4-substitute-phenyl) ethan-1-one oxime was synthesized by the reaction of 2aminophenol with different kinds of intermediates in several steps through both conventional and microwave techniques.All compounds were found to have an excellent degree of urease inhibitory potential ranging from 0.46 � 0.01 to 46.10 � 0.45 μM in compared with standard inhibitor acetohydroxamic acid with IC 50 320.70 � 4.24 μM. Structure-activity relationship was established in detail. In addition, we confirmed the binding interactions of compounds with enzymes using molecular docking.

show abstract

“…The difluorination of heterocyclic b-ketosulfones with Selectfluor afforded the corresponding gem-difluoromethylsulfones, which after baseinduced cleavage of the ketoaryl group allowed to access a series of difluoromethylsulfones (Eq. 46) [82,87]. The fluorination was carried out in acetonitrile but can also be performed in ionic liquids in which Selectfluor is soluble [88].…”

Section: ð44þ ð45þmentioning

confidence: 99%

Selectfluor and Its Analogs Electrophilic Fluorination for Preparing Alkyl Fluorides

Guyon¹,

Cahard²

2017

Fluorination

View full text Add to dashboard Cite

Synthesis of difluorinated β-ketosulfones and novel gem-difluoromethylsulfone-containing heterocycles as fluorinated building blocks

Cited by 25 publications

References 77 publications

Synthesis, Crystal Study, and Anti-Proliferative Activity of Some 2-Benzimidazolylthioacetophenones towards Triple-Negative Breast Cancer MDA-MB-468 Cells as Apoptosis-Inducing Agents

Synthesis, Crystal Study, and Anti-Proliferative Activity of Some 2-Benzimidazolylthioacetophenones towards Triple-Negative Breast Cancer MDA-MB-468 Cells as Apoptosis-Inducing Agents

Synthesis and Molecular Docking Studies of Potent Urease Inhibitors Based on Benzoxazole Scaffold

Selectfluor and Its Analogs Electrophilic Fluorination for Preparing Alkyl Fluorides

Contact Info

Product

Resources

About