Kinetic control in the formation of meso-dithia[3.3]-paracyclophane S,S′-dioxide

Barattucci, Anna; Bonaccorsi, Paola; Papalia, Teresa; Manganaro, Nadia; Gattuso, Giuseppe

doi:10.1016/j.tetlet.2014.07.082

Cited by 6 publications

(3 citation statements)

References 19 publications

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“…Compound 7a was subjected to an unrestricted conformer distribution calculation. Keeping in mind that 7a possesses limited conformational flexibility, 28 two relevant conformations emerged from the analysis, a ‘zig-zag’ (conformer A in Fig. 2) and a ‘folded’ one (B, Fig.…”

Section: Resultsmentioning

confidence: 99%

A two-site reactive platform in the synthesis of amino-functionalized amphiphilic molecules via sulfenic acids

Bonaccorsi

Gangemi

Greco³

et al. 2022

Org. Biomol. Chem.

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Section: Resultsmentioning

confidence: 99%

A two-site reactive platform in the synthesis of amino-functionalized amphiphilic molecules via sulfenic acids

Bonaccorsi

Gangemi

Greco³

et al. 2022

Org. Biomol. Chem.

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“…However, the most convenient procedure, for the generation of more than one sulfenic function in a single substrate, involved the use of sulfinyl precursors thermolyzing at 83 °C, for their stability and reactivity, producing final products in better total yields. Moreover, recent experimental observations led us to conclude that the formation of the two or three sulfenic functions is a stepwise process [ 38 , 39 ] that proceeds with the generation of the first sulfenic function and its addition or condensation to suitable molecules, followed by generation of the second sulfenic function and its reaction, and so forth ( Scheme 9 in Section 5 ).…”

Section: Glycoconjugated Disulfoxides and Disulfidesmentioning

confidence: 99%

Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products

et al. 2018

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Sulfenic acids as small molecules are too unstable to be isolated and their transient nature offers the possibility to involve them in concerted processes that lead to the obtainment of functional groups such as sulfoxides, sulfones, and disulfides. All these functions are present in a number of natural and synthetic drugs and can represent structural motives inducing biologically relevant properties. In this small review the generation and reactions of sulfenic acid bearing naturally occurring residues are described. Carbohydrate and aminoacid-derived sulfenic acids have been used in concerted addition with triple bonds to obtain alliin derivatives and thiosugars in enantiomerically pure form. Glycoconjugates with sulfinyl, sulfonyl, and disulfane functional groups and pyridine-derived disulfides have been obtained from bis- and tris-sulfinyl precursors of sulfenic acids. Small families of such compounds have been subjected to preliminary biological tests. Starting from the evidence that the control of molecular architecture and the presence of suitable functional groups can play a significant role on the exhibition of biological properties, apoptotic effects on malignant cells by glycoconjugates and inhibitory activity against the important human pathogen S. aureus by pyrimidine-derived disulfides have been found.

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“…However, the most convenient procedure, for the generation of more than one sulfenic function in a single substrate, involved the use of sulfinyl precursors thermolyzing at 83°C, for their stability and reactivity, producing final products in better total yields. Moreover, recent experimental observations led us to conclude that formation of the two or three sulfenic functions is a stepwise process [35,36] that proceeds with the generation of the first sulfenic function and its addition or condensation to suitable molecules, followed by generation of the second sulfenic function and its reaction, and so forth (Scheme 9 in paragraph 4).…”

Section: Glycoconjugated Disulfoxides and Disulfidesmentioning

confidence: 99%

Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products

Barattucci

Aversa

Mancuso

et al. 2018

Preprint

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Sulfenic acids as small molecules are too unstable to be isolated and their transient nature offers the possibility to involve them in concerted processes that lead to the obtainment of functional groups such as sulfoxides, sulfones and disulfides. All these functions are present in a number of natural and synthetic drugs and can represent structural motives inducing biological relevant properties. In this small review the generation and reactions of sulfenic acid bearing naturally occurring residues are described. Carbohydrate and aminoacid-derived sulfenic acids have been used in concerted addition to triple bonds to obtain alliin derivatives and thiosugars in enantiomerically pure form. Glycoconjugates with sulfinyl, sulfonyl and disulfane functional groups and pyridine-derived disulfides have been obtained from bis and tris-sulfinyl precursors of sulfenic acids. Small families of such compounds have been subjected to preliminary biological tests. Starting from the evidence that the control of molecular architecture and the presence of suitable functional groups can play a significant role on the exhibition of biological properties, apoptotic effects on malignant cells by glycoconjugates and inhibitory activity against the important human pathogen S. aureus by pyrimidine-derived disulfides have been found.

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Kinetic control in the formation of meso-dithia[3.3]-paracyclophane S,S′-dioxide

Cited by 6 publications

References 19 publications

A two-site reactive platform in the synthesis of amino-functionalized amphiphilic molecules via sulfenic acids

A two-site reactive platform in the synthesis of amino-functionalized amphiphilic molecules via sulfenic acids

Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products

Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products

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