Displacement of the 2-Methylmercapto Group in Pyrimidines Bearing a 5-Nitroso Substituent<sup>1</sup>

Cresswell, R. M.; Strauss, T.

doi:10.1021/jo01045a018

Cited by 15 publications

(8 citation statements)

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“…There are some precedents [5][6] indicating that a 5-nitroso group can act as strong activator of nucleophilic substitution of alkylthio groups from pyrimidines. However, the studies have not been, to our knowledge, extended to the activation of other leaving groups.…”

Section: Introductionmentioning

confidence: 99%

“…However, another strong electron-withdrawing group, the nitroso group, has received little attention as an activator of nucleophilic substitution, even when it is one of the most widely employed to introduce a nitrogen functionalisation at C (5) in pyrimidine derivatives during the synthesis of azaheterocycles fused with pyrimidine (i.e., purines, 8-azapurines, pteridines, etc.). There are some precedents [5][6] indicating that a 5-nitroso group can act as strong activator of nucleophilic substitution of alkylthio groups from pyrimidines. However, the studies have not been, to our knowledge, extended to the activation of other leaving groups.…”

Section: Introductionmentioning

confidence: 99%

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Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5‐nitroso

Marchal

Nogueras

Sánchez

et al. 2002

Journal of Heterocyclic Chem

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The nucleophilic substitution of 2‐mefhoxy groups in pyrimidine derivatives was strongly activated by introduction of a 5‐nitroso group on to the pyrimidine ring. The aminolysis of several 2‐methoxy‐5‐nitrosopyrimidine derivatives was performed at room temperature in hydroxylic as well as in non‐hydroxylic media with different primary amines in short time and good yields. The aminolysed substrates include 6‐[(per‐O‐acetyl)glycosyl]aminopyrimidines which afforded the corresponding 2‐aminopyrimidines without harming the acetyl protecting groups of the sugar moiety.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5‐nitroso

Marchal

Nogueras

Sánchez

et al. 2002

Journal of Heterocyclic Chem

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show abstract

“…Fox, I. Wempen, A. Hampton, and I. L. Doerr, ibid., 80, 1669 had been applied previously to both hydroxylamino-purines17 and hydroxylaminopyrimidines. 18 The high susceptibility to nucleophilic attack of 4alkylthiopteridines,19'20 2-alkylthiopteridines,20 and 4-alkoxypteridines21'22 has been noted previously.…”

Section: IIImentioning

confidence: 65%

Nucleophilic Displacement Reactions of 2-Amino-4-alkylthiopteridines^1-3

McCormack¹,

Mautner²

1964

J. Org. Chem.

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“…Accordingly, it was decided to introduce the desired 2,4-diamino substitution prior to the formation of the pteridine ring. Since dimethylamine, pyrrolidine and piperidine had been shown to displace the 2-methylthio group of 4,6-diamino-2-methylthio-5-nitrosopyrimidine (3) [ 21 ], the route envisaged here involved 5-nitrosation, 2-amination, then reduction and cyclization to give the pteridine ring system ( Figure 2 ).…”

Section: Resultsmentioning

confidence: 99%

Pteridine-2,4-Diamine Derivatives as Radical Scavengers and Inhibitors of Lipoxygenase that can Possess Anti-Inflammatory Properties

et al. 2015

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BackgroundReactive oxygen species are associated with inflammation implicated in cancer, atherosclerosis and autoimmune diseases. The complex nature of inflammation and of oxidative stress suggests that dual-target agents may be effective in combating diseases involving reactive oxygen species.ResultsA novel series of N-substituted 2,4-diaminopteridines has been synthesized and evaluated as antioxidants in several assays. Many exhibited potent lipid antioxidant properties, and some are inhibitors of soybean lipoxygenase, IC50 values extending down to 100 nM for both targets. Several pteridine derivatives showed efficacy at 0.01 mmol/kg with little tissue damage in a rat model of colitis. 2-(4-methylpiperazin-1-yl)-N-(thiophen-2-ylmethyl)pteridin-4-amine (18f) at 0.01 mmol/kg exhibited potent anti-inflammatory activity (reduction by 41%).ConclusionThe 2,4-diaminopteridine core represents a new scaffold for lipoxygenase inhibition as well as sustaining anti-inflammatory properties.

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Displacement of the 2-Methylmercapto Group in Pyrimidines Bearing a 5-Nitroso Substituent¹

Cited by 15 publications

References 1 publication

Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5‐nitroso

Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5‐nitroso

Nucleophilic Displacement Reactions of 2-Amino-4-alkylthiopteridines^1-3

Pteridine-2,4-Diamine Derivatives as Radical Scavengers and Inhibitors of Lipoxygenase that can Possess Anti-Inflammatory Properties

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Displacement of the 2-Methylmercapto Group in Pyrimidines Bearing a 5-Nitroso Substituent1

Cited by 15 publications

References 1 publication

Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5‐nitroso

Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5‐nitroso

Nucleophilic Displacement Reactions of 2-Amino-4-alkylthiopteridines1-3

Pteridine-2,4-Diamine Derivatives as Radical Scavengers and Inhibitors of Lipoxygenase that can Possess Anti-Inflammatory Properties

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Displacement of the 2-Methylmercapto Group in Pyrimidines Bearing a 5-Nitroso Substituent¹

Nucleophilic Displacement Reactions of 2-Amino-4-alkylthiopteridines^1-3