New dithio-bis-(diaroylmethanes) and acetyl diaroylchloromethyl disulfides: Attractive synthons and precursors for the liberation of highly reactive dithiiranes or thiosulfines

Franek, W.

doi:10.1007/bf00807029

Cited by 20 publications

(6 citation statements)

References 15 publications

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“…Synthesis of 1,3-Di-(4-tolyl)-propane-1,3-dione (1). 1 was prepared by a modification of the literature procedure . A solution of 4-methyl-benzoyl acid methyl ester (24.75 g, 165 mmol) and tolyl acetone (20.82 g, 150 mmol) in 10 mL dry THF, and 10 mL dry DMSO was added dropwise into a suspension of NaH (4 g, 166 mmol) in 45 mL dry THF and 35 mL dry DMSO under an argon atmosphere at 3∼5 °C with vigorous stirring.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of Ruthenium and Rhenium Nucleosides

et al. 2007

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We report the synthesis and characterization of new ruthenium and rhenium nucleosides [Ru(tolyl-acac) 2 (IMPy)-T] (tolyl-acac ) di(p-methylbenzonatemethane), IMPy ) 2′-iminomethylpyridine, T ) thymidine) ( 5) and [Re(CO) 3 -(IMPy)-T]Cl (9), respectively. Structural analysis of 9 shows that the incorporation of this metal complex causes minimal perturbation to the sugar backbone and the nucleobase. Eletrochemical (5, E 1/2 ) 0.265 V vs NHE; 9, E 1/2 ) 1.67 V vs NHE), absorption (5, λ max ) 600, 486 nm; 9, λ max ) 388 nm), and emission (9, λ max ) 770 nm, π ) 17 ns) data indicate that 5 and 9 are suitable probes for DNA-mediated ground-state electron-transfer studies. The separation and characterization of diastereoisomers of 5 and bipyridyl-based ruthenium nucleoside [Ru(bpy) 2 -(IMPy)-T] 2+ (7) are reported.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of Ruthenium and Rhenium Nucleosides

et al. 2007

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“…For example, 1,2,4-trithiiolane ( 2a ) has relevance to the sulfur cycle − and astrochemistry, − underscoring interest in its cycloreversion. Dithiiranes (CR 2 SS) and their valence isomers, the thiosulfines (R 2 CS 2 ), have also been proposed as intermediates in reaction mechanisms leading to sulfur-rich compounds. − To date, however, substituted forms of thiosulfine (thiocarbonyl S -sulfides) have received the most attention. − …”

Section: Introductionmentioning

confidence: 99%

Thioformaldehyde S-Sulfide, Sulfur Analogue of the Criegee Intermediate: Structures, Energetics, and Rovibrational Analysis

et al. 2017

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The ephemeral Criegee intermediate, first postulated over 70 years ago, has only recently been isolated in the gas phase. The sulfur analogue of this canonical zwitterion, thioformaldehyde S-sulfide, has eluded similar analysis; however, argon matrix isolation has been achieved ( Angew. Chem., Int. Ed. 2001 , 40 , 393 - 396 ). Here thioformaldehyde S-sulfide and its valence isomer dithiirane are examined with high-level coupled-cluster methods, including the minimum-energy pathway for interconversion. Relative enthalpies calculated from extrapolated energies at the complete basis set limit of the full CCSDTQ method are reported. Isomerization from thioformaldehyde S-sulfide to the lower-lying dithiirane (-7.2 kcal mol) is predicted to include a 27.0 kcal mol barrier. Harmonic and anharmonic vibrational frequencies are also predicted using second-order vibrational perturbation theory. These results should aid in future gas-phase identification.

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“…The aryl isocyanates intermediates ( 11a–h ) were prepared according to [scheme 2] starting from the corresponding acids ( 8a–h ), converting them to the acid chloride ( 9a–h ) using thionyl chloride under reflux conditions [26] , then reacting the appropriate acid chloride with sodium azide in acetone for 30 min at 0°C to give the corresponding aryl azides ( 10a–h ) [27] , finally Curtis rearrangement of the aryl azides ( 10a–h ) to the corresponding aryl isocyanates ( 11a–h ) was achieved by heating the aryl azides for 3 hours at 70°C in dry benzene [28] .…”

Section: Resultsmentioning

confidence: 99%

Applying Ligands Profiling Using Multiple Extended Electron Distribution Based Field Templates and Feature Trees Similarity Searching in the Discovery of New Generation of Urea-Based Antineoplastic Kinase Inhibitors

et al. 2012

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This study provides a comprehensive computational procedure for the discovery of novel urea-based antineoplastic kinase inhibitors while focusing on diversification of both chemotype and selectivity pattern. It presents a systematic structural analysis of the different binding motifs of urea-based kinase inhibitors and the corresponding configurations of the kinase enzymes. The computational model depends on simultaneous application of two protocols. The first protocol applies multiple consecutive validated virtual screening filters including SMARTS, support vector-machine model (ROC = 0.98), Bayesian model (ROC = 0.86) and structure-based pharmacophore filters based on urea-based kinase inhibitors complexes retrieved from literature. This is followed by hits profiling against different extended electron distribution (XED) based field templates representing different kinase targets. The second protocol enables cancericidal activity verification by using the algorithm of feature trees (Ftrees) similarity searching against NCI database. Being a proof-of-concept study, this combined procedure was experimentally validated by its utilization in developing a novel series of urea-based derivatives of strong anticancer activity. This new series is based on 3-benzylbenzo[d]thiazol-2(3H)-one scaffold which has interesting chemical feasibility and wide diversification capability. Antineoplastic activity of this series was assayed in vitro against NCI 60 tumor-cell lines showing very strong inhibition of GI50 as low as 0.9 uM. Additionally, its mechanism was unleashed using KINEX™ protein kinase microarray-based small molecule inhibitor profiling platform and cell cycle analysis showing a peculiar selectivity pattern against Zap70, c-src, Mink1, csk and MeKK2 kinases. Interestingly, it showed activity on syk kinase confirming the recent studies finding of the high activity of diphenyl urea containing compounds against this kinase. Allover, the new series, which is based on a new kinase scaffold with interesting chemical diversification capabilities, showed that it exhibits its “emergent” properties by perturbing multiple unexplored kinase pathways.

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New dithio-bis-(diaroylmethanes) and acetyl diaroylchloromethyl disulfides: Attractive synthons and precursors for the liberation of highly reactive dithiiranes or thiosulfines

Cited by 20 publications

References 15 publications

Synthesis and Characterization of Ruthenium and Rhenium Nucleosides

Synthesis and Characterization of Ruthenium and Rhenium Nucleosides

Thioformaldehyde S-Sulfide, Sulfur Analogue of the Criegee Intermediate: Structures, Energetics, and Rovibrational Analysis

Applying Ligands Profiling Using Multiple Extended Electron Distribution Based Field Templates and Feature Trees Similarity Searching in the Discovery of New Generation of Urea-Based Antineoplastic Kinase Inhibitors

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