levo-2,3-Dinitroxybutane

McKay, A. F.; Meen, R. H.; Wright, George F

doi:10.1021/ja01181a524

Cited by 10 publications

(13 citation statements)

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“…Formation of the thiazoline derivative is reminiscent of the preparation of cyclic nitroguanidine derivatives from diamines and nitroguanidine with liberation of ammonia (21,22). The possibility that 2-nitramino-4-carboxylthiazoline might arise from reaction of cysteine with N-methyl-N1-nitroguanidine can be eliminated, since no reaction took place on mixing cysteine and N-methyl-N1-nitroguanidine for 20 h at room temperature in aqueous ethanol.…”

Section: Reactions Of Cysteine With Ngmentioning

confidence: 99%

Reactions of cysteine with N-methyl-N-nitroso-p-toluenesulfonamide and N-methyl-N′-nitro-N-nitrosoguanidine

Schulz¹,

McCalla²

1969

Can. J. Chem.

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The reaction between cysteine and N-methyl-N-nitroso-p-toluenesulfonamide affords almost quantitative yields of cystine and N-methyl-p-toluenesuIfonaniide. A mechanism based on the intermediacy of the S-nitroso derivative of cysteine and the intermediate formation of nitric oxide is proposed. Nitrous oxide is shown to be a final product. In the reaction of cysteine with N-methyl-N'-nitro-N-nitrosoguanidine a substantial yield of 2-nitramino-4-carboxyl-thiazoline is obtained. Cystine, N-methyl-N'-nitroguanidine and S-methylcysteine are formed in lesser amounts. The major product arises from nucleophilic attack on the iniino carbon of N-methyl-N'-nitro-N-nitrosoguanidine. Concomitant elimination of the methylnitrosamino group accounts for the methylating ability of the system. Canadian Journal of Chemistry, 47, 2021 (1969) Previous work in this laboratory has shown that deoxyribonucleic acid (DNA) becomes methylated when it is allowed to react in vitro with either N-methyl-N'-nitro-N-nitrosoguanidine (NG) or with N-methyl-N-nitroso-p-toluenesulfonamide (MNTS) (1). Addition of cysteine to the reaction mixture was found to increase methylation by N G but to decrease dramatically methylation by MNTS, results which are of considerable interest in view of biological studies showing that cysteine has a protective action against certain types of alkylating agents (2).Both N G and MNTS are well-established sources of diazomethane in their reactions with aqueous base (3,4). For the reactions of N G and MNTS with nucleophilic reagents other than oxygen nucleophiles, a variety of products are reported. McKay and Wright (5) demonstrated that primary alkyl or aryl amines react with N G with the elimination of the methylnitrosamino group and the formation of N-substituted nitroguanidines. The only secondary amine to react with N G to give a Ndisubstituted-Nf-nitroguanidine is dimethylamine. Reaction of N G with other secondary amines resulted in denitrosation (6). In the reaction of N G with azide ion the methylnitrosamino group is eliminated and 5-nitroaminotetrazole is formed by cyclization of the intermediate nitrogiianylazide (7). The reaction between MNTS and piperidine results in transfer of the nitroso group to form N-nitrosopiperidine without the formation of any diazomethane (4). Low yields of diphenylnitrosamine are reported to result from reaction of MNTS with diphenylamine (8).Thus, while the existing literature pointed to the fact that the N-methyl-N-nitroso compounds under consideration exhibit two centers susceptible to nucleophilic attack, resulting in loss of the methylnitrosamino group and the nitroso function respectively, no information was available on their reactions with mercaptans. We report here data that provide a reasonable explanation for the difference in the behavior of N G and MNTS in the presence of cysteine. Results and Discussion Reactions of Cysteitze rvith M N T SThe reactions of cysteine with MNTS were carried out at room temperature in aqueous 25 % ethanol at pH 7 in an atmosphere of nit...

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Section: Reactions Of Cysteine With Ngmentioning

confidence: 99%

Reactions of cysteine with N-methyl-N-nitroso-p-toluenesulfonamide and N-methyl-N′-nitro-N-nitrosoguanidine

Schulz¹,

McCalla²

1969

Can. J. Chem.

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“…[17]. Nitroguanidine (17) 55 (m, 1 H, H a -1, and m, 1 H, H b -1 The syntheses of guanidines 1 and 2 were carried out modified according to ref.…”

Section: (±)-4-hexyl-n 2 -Nitro-2-imidazolidinimine (18 J)mentioning

confidence: 99%

Novel High Energy Intermediate Analogues with Triazasterol‐Related Structures as Inhibitors of Ergosterol Biosynthesis Part I: Synthesis and Antifungal Activity of N‐alkyl‐N′‐(phenethyl‐ and cyclohexenylethyl)guanidines and N²‐Substituted 2‐Imidazolinamines

Gößnitzer

Malli

Schuster

et al. 2002

Archiv der Pharmazie

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A series of N-alkyl-N'-(phenethyl- and cyclohexenylethyl) guanidines and N(2)- and N(2), 4-substituted imidazolin-2-amine hydrochlorides with triazasterol-related structures was designed and synthesized as stable analogues to mimic high energy intermediates of ergosterol biosynthesis. The in vitro antifungal susceptibility tests with a standard panel of pathogenic fungi revealed moderate to strong antimycotic effects of the sixteen prepared compounds, in some cases comparable with the activity observed for itraconazole.

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“…Several procedures for the synthesis of 2-nitroiminoimidazolidine were developed. Hafner and Evans [116] obtained this compound in 72.1% yield by reaction of S-methyl-N-nitroisothiourea (95) Presumably, the most convenient procedure for the synthesis of 2-nitroiminoimidazolidine (97) is that proposed by McKay and Wright [118,119]. According to the authors, compound 97 is formed by reaction of nitroguanidine (99) with ethylenediamine dihydrochloride (100) and potassium hydroxide in water on heating (Scheme 37).…”

mentioning

confidence: 99%

Advances in the synthesis of neonicotinoids

Ковганко

Kashkan

2004

Russ J Org Chem

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levo-2,3-Dinitroxybutane

Cited by 10 publications

References 0 publications

Reactions of cysteine with N-methyl-N-nitroso-p-toluenesulfonamide and N-methyl-N′-nitro-N-nitrosoguanidine

Reactions of cysteine with N-methyl-N-nitroso-p-toluenesulfonamide and N-methyl-N′-nitro-N-nitrosoguanidine

Novel High Energy Intermediate Analogues with Triazasterol‐Related Structures as Inhibitors of Ergosterol Biosynthesis Part I: Synthesis and Antifungal Activity of N‐alkyl‐N′‐(phenethyl‐ and cyclohexenylethyl)guanidines and N²‐Substituted 2‐Imidazolinamines

Advances in the synthesis of neonicotinoids

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levo-2,3-Dinitroxybutane

Cited by 10 publications

References 0 publications

Reactions of cysteine with N-methyl-N-nitroso-p-toluenesulfonamide and N-methyl-N′-nitro-N-nitrosoguanidine

Reactions of cysteine with N-methyl-N-nitroso-p-toluenesulfonamide and N-methyl-N′-nitro-N-nitrosoguanidine

Novel High Energy Intermediate Analogues with Triazasterol‐Related Structures as Inhibitors of Ergosterol Biosynthesis Part I: Synthesis and Antifungal Activity of N‐alkyl‐N′‐(phenethyl‐ and cyclohexenylethyl)guanidines and N2‐Substituted 2‐Imidazolinamines

Advances in the synthesis of neonicotinoids

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About

Novel High Energy Intermediate Analogues with Triazasterol‐Related Structures as Inhibitors of Ergosterol Biosynthesis Part I: Synthesis and Antifungal Activity of N‐alkyl‐N′‐(phenethyl‐ and cyclohexenylethyl)guanidines and N²‐Substituted 2‐Imidazolinamines