Oxidationen an Thiourethanen, 10. α‐Carbamoylsulfoxide und ‐sulfone, 2. Thiosulfonatbildung bei der Hydrolyse cyclischer α‐Carbamoylsulfoxide

Hanefeld, Wolfgang; Jalili, M. A.

doi:10.1002/jlac.198619861012

Cited by 13 publications

(7 citation statements)

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“…This suggested that two of the three new oxygen atoms are at the S and the last is assigned as the hydroxyl group at N. Further evidence for this was the disappearance of the H−N at δ 6.1. In addition, the amide IR resonance in 2 is absent in 3 , and a new resonance at 1756 cm -1 appeared, indicating the presence of a CONOH system . The OH band at 3448 cm -1 is significantly increased in intensity for 3 , indicating the presence of two OH groups in 3 versus one OH group in 2 .…”

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confidence: 94%

“…In addition the amide IR resonance in 2 is absent in 3 and a new resonance at 1756 cm −1 appeared, indicating the presence of a CONOH system. 11 The OH band at 3448 cm −1 is significantly increased in intensity for 3 indicating the presence of two OH groups in 3 versus one OH group in 2. The IR showed a strong band at 1051 cm −1 indicating the presence of an SO 2 moiety.…”

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confidence: 96%

“…9,10 It has also been shown that oxygenation of the sulfur atom adjacent to the carbonyl of a 5-membered thiazolidinone will move chemical shifts upfield by ~10 ppm. 11 This suggested that two of the three new oxygen atoms are at the S and the last is assigned as the hydroxyl group at N. Further evidence for this was the disappearance of the H-N at δ6.1. In addition the amide IR resonance in 2 is absent in 3 and a new resonance at 1756 cm −1 appeared, indicating the presence of a CONOH system.…”

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confidence: 98%

“…The C-18 also moved upfield from δ 175.3 to 157.3. The chemical shift of the carbonyl carbon of a five-membered lactam ring will move upfield around 15 ppm when the lactam nitrogen is hydroxylated. , It has also been shown that oxygenation of the sulfur atom adjacent to the carbonyl of a five-membered thiazolidinone will move chemical shifts upfield by ∼10 ppm . This suggested that two of the three new oxygen atoms are at the S and the last is assigned as the hydroxyl group at N. Further evidence for this was the disappearance of the H−N at δ 6.1.…”

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Latrunculin with a Highly Oxidized Thiazolidinone Ring: Structure Assignment and Actin Docking

et al. 2007

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A new latrunculin, oxalatrunculin B (3), was isolated from Red Sea sponge Negombata corticata. Extensive spectroscopic analysis revealed an unprecedented heterocycle in which the rare thiazolidinone ring found in latrunculins was oxidized with three additional oxygens. An actin polymerization inhibition assay agreed with MM-PBSA free energy calculations that 3 binds more weakly than latrunculin B to actin. Significant antifungal and anticancer activity of 3 was found, suggesting an alternate target in addition to actin for latrunculin bioactivity.Latrunculins A (1) and B (2) (Fig. 1) were first isolated from Negombata magnifica (Keller) (formerly Latrunculia magnifica), discovered from the Red Sea. 1 Among the characteristic features of these natural products is the presence of a macrocyclic lactone ring of 14 or 16 carbon atoms and a 2-thiazolidinone moiety (Figure 1). 2,3 In vitro experiments revealed that the latrunculins disrupt actin polymerization, 4 a possible target for cancer. 5A recent study has also reported antimigratory and antiangiogenic activity of latrunculins, adding to their possible utility in the control of cancer. 6 In addition to significant ichthyotoxic and cytotoxic properties, the latrunculins are also antiviral against herpes simplex type 1 virus (HSV-1). 7Several new latrunculins including natural, synthetic or semisynthetic analogs have been reported recently. 6,8 We report here the structure assignment and bioactivity of a unique new jkhalifa_99@yahoo.com, rjd@olemiss.edu, mthamann@olemiss.edu. As further evidence for this, combustion analysis on 3 showed 53.6% carbon, 6.51% hydrogen, 3.16% nitrogen, 28.6% oxygen and 6.34% sulfur. 13 C NMR indicated that the carbon skeleton of 3 consisted of 2 methyl carbons, 7 methylenes, 7 methines and 4 quaternary carbon atoms, which is identical to the carbon multiplicities of 2. The 13 C NMR chemical shifts for the 14-membered and tetrahydropyran rings were in close agreement with those of 2 revealing that additional oxygenation must occur at the heteroatoms. Significant differences were found in the chemical shifts of the thiazolidinone ring. The C-17 resonance shifted downfield from δ28.5 to δ49.9 indicating the introduction of a neighboring oxygen atom. C-16 shifted slightly upfield so the only possible position for oxidation was at the sulfur atom. C-18 also moved upfield from δ175.3 to δ157.3. The chemical shift of the carbonyl carbon of a 5-membered lactam ring will move upfield around 15ppm when the lactam nitrogen is hydroxylated. 9,10 It has also been shown that oxygenation of the sulfur atom adjacent to the carbonyl of a 5-membered thiazolidinone will move chemical shifts upfield by ~10 ppm. 11 This suggested that two of the three new oxygen atoms are at the S and the last is assigned as the hydroxyl group at N. Further evidence for this was the disappearance of the H-N at δ6.1. In addition the amide IR resonance in 2 is absent in 3 and a new resonance at 1756 cm −1 appeared, indicating the presence of a CONOH system. 11 The OH...

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confidence: 94%

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confidence: 96%

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confidence: 98%

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Latrunculin with a Highly Oxidized Thiazolidinone Ring: Structure Assignment and Actin Docking

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“…CrO 3 ) oder durch die schwierige Entsorgung (Chromate, Schwermetalle). Zudem geht die Oxidation oftmals über das gewünschte Produkt II hinaus bis zur Stufe der Thiolurethan-Soxide III oder -S,S-dioxide IV [21], die durch leicht erfolgende Hydrolysereaktionen das Produktgemisch noch heterogener machen [22].…”

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Oxidationen an Thiourethanen. 16 [1]; Elektrochemische Oxidationen. 2 [2]: Elektrochemische Oxidationen von cyclischen Dithiourethanen, analytische Peakpotentialermittlung

Hanefeld

Schaible

2000

J. prakt. Chem.

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659 Cyclische Thiolurethane vom Typ II verfügen über eine breite biologische Wirksamkeit [3]. Im Vergleich zu den 2-Thioxo-Analoga I mit cyclischer Dithiourethanstruktur zeigen sie bei gleichem Substitutionsmuster teilweise gleichartige, in den meisten Fällen jedoch stark abweichende biologische Wirkprofile [4]. Ähnliche Effekte wurden bei anderen Verbindungen mit Dithiourethanbzw. Thiolurethanstruktur schon mehrfach beschrieben [5 -7]. Oxidationen an Thiourethanen. 16 [1]; Elektrochemische Oxidationen. 2 [2]: Elektrochemische Oxidationen von cyclischen Dithiourethanen, analytische PeakpotentialermittlungAbstract. It is possible to oxidize carbamodithioates of type I to the related carbamothioates of type II by electrochemical anodic oxidation. As analytical methods have been applied direct current voltammetry, differential pulse polarography

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Thiosulfonates as Emerging Reactants: Synthesis and Applications

et al. 2019

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The synthetic strategies towards thiosulfonates (RSO2SR1) are comprehensively reviewed from their original discovery to recent advances. Incorporation of the green credentials of the synthetic procedures towards thiosulfonates allows one to judge the merits of the state of the art, beyond the typical yield of a product and availability of the reactants. As reactant for organic transformations, thiosulfonates are particularly interesting given their possibility to react with nucleophiles, electrophiles and radicals. This review aims to give researchers, not familiar with the field, a good understanding of the general applications of thiosulfonates, while not skipping the recent important advances. The related, but less explored, selenosulfonates (RSO2SeR1) are also covered.

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Oxidationen an Thiourethanen, 10. α‐Carbamoylsulfoxide und ‐sulfone, 2. Thiosulfonatbildung bei der Hydrolyse cyclischer α‐Carbamoylsulfoxide

Abstract: Bei der Hydrolyse cyclischer ci-Carbamoylsulfoxide des Thiazintyps 1 und des Thiazolidintyps 4 werden Thiosulfonsaureester des Typs 12 bzw. 14 erhalten, deren neuartige Strukturen durch Spektren und unabhangige Synthesen belegt werden.

Cited by 13 publications

References 6 publications

Latrunculin with a Highly Oxidized Thiazolidinone Ring: Structure Assignment and Actin Docking

Latrunculin with a Highly Oxidized Thiazolidinone Ring: Structure Assignment and Actin Docking

Oxidationen an Thiourethanen. 16 [1]; Elektrochemische Oxidationen. 2 [2]: Elektrochemische Oxidationen von cyclischen Dithiourethanen, analytische Peakpotentialermittlung

Thiosulfonates as Emerging Reactants: Synthesis and Applications

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