Selective and facile oxidative desulfurization of thioureas and thiobarbituric acids with singlet molecular oxygen generated from <i>trans-</i>3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane

Azarifar, Davood; Golbaghi, Maryam

doi:10.1080/17415993.2015.1082181

Cited by 23 publications

(6 citation statements)

References 60 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Prepared from 4-CA and 4-chlorophenyl isocyanate. Yield: 86% (pinkish solid): mp 223–224 °C; LC/MS (70 eV) m / z (%): 281 [M + ]; IR (KBr): 3296 (NH), 1651 (C=O) cm −1 ; 1 H NMR spectrum was in agreement with the literature [ 42 ]. Anal.…”

Section: Methodssupporting

confidence: 78%

Searching for Small Molecules as Antibacterials: Non-Cytotoxic Diarylureas Analogues of Triclocarban

et al. 2021

View full text Add to dashboard Cite

Triclocarban (TCC), a broad-spectrum lipophilic antimicrobial agent, is a diarylurea derivative that has been used for more than 60 years as a major ingredient of toys, clothing, food packaging materials, food industry floors, medical supplies and especially of personal care products, such as soaps, toothpaste and shampoo. In September 2016, the U.S. FDA banned nineteen antimicrobial ingredients, including TCC, in over-the-counter consumer antiseptic wash products, due to their toxicity. Withdrawal of TCC has prompted efforts to search for new antimicrobial compounds. In this paper, we present the synthesis and biological evaluation, as antibiotic and non-cytotoxic agents, of a series of diarylureas, analogues of TCC. These compounds are characterized by an intriguingly simple chemistry and can be easily synthesized. Among the synthesized compounds, 1ab and 1bc emerge as the most interesting compounds as they show the same activity of TCC (MIC = 16 µg/mL) against Staphylococcus aureus, and a higher activity than TCC against Enterococcus faecalis (MIC = 32 µg/mL versus MIC = 64 µg/mL). Moreover, 1ab and 1bc show no cytotoxicity towards the human mammary epithelial cells MCF-10A and embryonic kidney epithelial cells Hek-293, in opposition to TCC, which exhibits a marked cytotoxicity on the same cell lines and shows a good antitumor activity on a panel of cell lines tested.

show abstract

Section: Methodssupporting

confidence: 78%

Searching for Small Molecules as Antibacterials: Non-Cytotoxic Diarylureas Analogues of Triclocarban

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The di(hydroperoxy)alkane adducts 1 – 9 are amenable to the classical H 2 O 2 based organic syntheses mentioned above. Another important application targets the oxidation of sulfides for academic purposes, but also for the energy saving and efficient oxidative desulfurization of petroleum batches . Once the fundamental insights about sulfide oxidation with 1 – 9 are gained, adducts of P‐chiral phosphine oxides could also be applied for the enantioselective synthesis of sulfoxides …”

Section: Resultsmentioning

confidence: 99%

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Ahn

Bhuvanesh

Blümel

2017

Chemistry A European J

View full text Add to dashboard Cite

The di(hydroperoxy)alkane adducts of phosphine oxides 1-9, Ph PO⋅(HOO) CMe , Cy PO⋅(HOO) CMe , Ph PO⋅ (HOO) CMeEt, Cy PO⋅(HOO) CMeEt, Cy PO⋅(HOO) CEt , Cy PO⋅ (HOO) C(CH ) , Cy PO⋅(HOO) CMePh, (Ph P(O)CH CH P(O)Ph )⋅ ((HOO) CEt ) , and Ph P(O)CH P(O)Ph ⋅(HOO) CMe , respectively, are synthesized and fully characterized by H, C, and P NMR, and IR spectroscopies. Single crystal X-ray structures are reported for 3-9. Different one-pot synthetic pathways, starting from R P, R PO, R PO⋅H O, and R PO⋅H O are explored and discussed and a mechanism for the formation of the di(hydroperoxy)alkane adducts of phosphine oxides is suggested. The longevity of the adducts is tested by monitoring the oxidation of Ph P with quantitative NMR. The solubilities of the adducts in organic solvents are presented, and their applicability as stoichiometric oxidizing agents for the selective oxidation of sulfides to sulfoxides is reported.

show abstract

“…Oxygenated sulfur compounds, like sulfinic and sulfonic acids, as well as the carbonyl analog of 8-TG, have not been detected. Considering what has been previously described for 6-TG and the proposed mechanism hypothesized for thiourea in the presence of singlet oxygen [22], we propose that a similar [2 + 2] attack of 1 O 2 on the thione moiety would lead to a thioperoxyl radical via 4-membered-ring opening. Subsequently, this unstable intermediate could, instead of proceeding to an oxygenated sulfur compound, evolve to form a carbene, leading afterwards to guanosine ( 2 ) (Scheme 3b).…”

Section: Resultsmentioning

confidence: 51%

“…Because of the highly applicability, several research groups have been interested in the redox chemistry of thioureas and have reported detailed mechanistic studies for these transformations. The reactivity of thioureas with hydrogen peroxide [20], common reducing agents such as K and NaBH 4 [21], singlet oxygen [22], and upon pulse radiolysis in both reducing and oxidizing conditions have been studied [23,24,25,26,27,28,29], outlining multiple mechanistic scenarios.…”

Section: Introductionmentioning

confidence: 99%

Converging Fate of the Oxidation and Reduction of 8-Thioguanosine

et al. 2019

View full text Add to dashboard Cite

Thione-containing nucleobases have attracted the attention of the scientific community for their application in oncology, virology, and transplantology. The detailed understanding of the reactivity of the purine derivative 8-thioguanosine (8-TG) with reactive oxygen species (ROS) and free radicals is crucial for its biological relevance. An extensive investigation on the fate of 8-TG under both reductive and oxidative conditions is here reported, and it was tested by employing steady-state photooxidation, laser flash photolysis, as well as γ-radiolysis in aqueous solutions. The characterization of the 8-TG T1 excited state by laser flash photolysis and the photooxidation experiments confirmed that singlet oxygen is a crucial intermediate in the formation of the unexpected reduced product guanosine, without the formation of the usual oxygenated sulfinic or sulfonic acids. Furthermore, a thorough screening of different radiolytic conditions upon γ-radiation afforded the reduced product. These results were rationalized by performing control experiments in the predominant presence of each reactive species formed by radiolysis of water, and the mechanistic pathway scenario was postulated on these bases.

show abstract

Selective and facile oxidative desulfurization of thioureas and thiobarbituric acids with singlet molecular oxygen generated from trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane

Cited by 23 publications

References 60 publications

Searching for Small Molecules as Antibacterials: Non-Cytotoxic Diarylureas Analogues of Triclocarban

Searching for Small Molecules as Antibacterials: Non-Cytotoxic Diarylureas Analogues of Triclocarban

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Converging Fate of the Oxidation and Reduction of 8-Thioguanosine

Contact Info

Product

Resources

About