Metathetical Reactions of Silver Salts in Solution. II. The Synthesis of Alkyl Sulfonates<sup>1</sup>

Emmons, William D.; Ferris, Arthur F.

doi:10.1021/ja01105a509

Cited by 70 publications

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“…Elution conditions for TLC and HPLC varied and are specified individually for each compound below. Bis(tosyloxy) methane was prepared as previously reported from diiodomethane and an excess of silver tosylate, 16 and purification was accomplished by flash chromatography on silica gel, eluting with a 4:1 mixture of hexanes:ethyl acetate. [8,8,8]hexacosane (Kryptofix).…”

Section: Methodsmentioning

confidence: 99%

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Improved synthesis of [¹⁸F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations

Neal¹,

Apana²,

Berridge

2005

Labelled Comp Radiopharmac

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Section: Methodsmentioning

confidence: 99%

“…[14][15][16] Reaction of Based upon their observations, some modifications were made to determine the affect on yield. In the present work, the reaction was carried out in acetonitrile, dimethylformamide and acetone, using 18 13,20 based upon analysis by TLC and HPLC.…”

Section: Introductionmentioning

confidence: 99%

Improved synthesis of [¹⁸F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations

Neal¹,

Apana²,

Berridge

2005

Labelled Comp Radiopharmac

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“…The other esters were synthesised according to the method of Emmons and Ferris (1953) All dimethanesulphonates were freshly dissolved in DMSO at a concentration of 250 mM and then diluted as appropriate in alkylation buffer. Melphalan was diluted from a stock solution 10 mM in 0.1 M HCI stored frozen.…”

Section: Chemicalsmentioning

confidence: 99%

DNA interstrand crosslinking and sequence selectivity of dimethanesulphonates

Ponti

Souhami²,

Fox³

et al. 1991

Br J Cancer

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Summary Members of the homologous series of alkanediol dimethanesulphonates of general formula H3C.SO20.(CH2)n.O.SO2.CH3 have been tested for their ability to produce DNA interstrand crosslinking and DNA sequence selectivity of guanine-N7 alkylation. In a sensitive crosslinking gel assay the efficiency of DNA interstrand crosslink formation, dependent on the ability of the alkylating moiety to span critical nucleophilic distances within the DNA, was found at 6 h to be 1,6-hexanediol dimethanesulphonate (Hexa-DMS) (n = 6) > methylene dimethanesulphonate (MDMS) (n = 1) > 1,8-octanediol dimethanesulphonate (Octa-DMS) (n = 8) > Busulphan (n = 4). The DNA interstrand crosslinking produced by MDMS was not due to either of its hydrolysis products, formaldehyde or methanesulphonic acid (MSA). In contrast the extent of monoalkylation at guanine-N7 as determined by a modified DNA sequencing technique was found to be Busulphan>>Hexa-DMS = Octa-DMS, with a sequence selectivity somewhat less than that of other chemotherapeutic alkylating agents such as nitrogen mustards. MDMS at high levels induced a non-specific depurination as a result of the reduction in pH resulting from MSA release. More strikingly MDMS (and MSA) produced a single strong site of guanine reaction (depurination) in a guanine-rich 276 base pair fragment of pBR322 DNA in the sequence of 5'-ATGGTGG-3'. This was observed when non-specific depurination was negligible and was not seen with formic acid. Thus structurally similar alkylating agents can differ in their type and extent of DNA monoalkylation and interstrand crosslinking, and in some cases (e.g. MDMS/MSA) produce reactions with a high degree of selectivity.

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“…Strophanthidin-3-tosyloxy-acetate (STA) and digitoxigenin-3-tosyloxy-acetate (DTA) were prepared from the corresponding 3-bromoacetates of strophanthidin (Hokin et al, 1966) and digitoxigenin (Abramson & Cho, 1971) by reaction with silver p-toluenesulphonate in acetonitrile according to the method of Emmons & Ferris (1953 and characterization will be given elsewhere (Rogatti, thesis). The chemical structures are given in Figure 1.…”

Section: Methodsmentioning

confidence: 99%

ACTIVE SITE‐DIRECTED ALKYLATION OF Na⁺‐K⁺‐ATPase BY DIGITALIS SULPHONATE DERIVATIVES OF DIFFERENT LIPOPHILICITY

Fricke

Klaus

Rogatti

1981

British J Pharmacology

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1 Sulphonate derivatives of k-strophanthidin and digitoxigenin were tested as active site-directed labels of Na+-K+-adenosine triphosphatase (Na+-K+-ATPase) from guinea-pig heart. 2 Lipophilicity ranged between P = 93 for strophanthidin-3-tosyloxy-acetate (STA) and P = 3028 for digitoxigenin-3-tosyloxy-acetate (DTA). 3 Although the alkylating moiety of STA and DTA was identical, the reversibility of Na+-K+-ATPase inhibition varied appreciably (82% and 35% respectively).4 It is concluded that lipophilicity contributes considerably to the irreversible binding of alkylating cardiotonic steroids to myocardial Na+-K+-ATPase.

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Metathetical Reactions of Silver Salts in Solution. II. The Synthesis of Alkyl Sulfonates¹

Cited by 70 publications

References 0 publications

Improved synthesis of [¹⁸F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations

Improved synthesis of [¹⁸F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations

DNA interstrand crosslinking and sequence selectivity of dimethanesulphonates

ACTIVE SITE‐DIRECTED ALKYLATION OF Na⁺‐K⁺‐ATPase BY DIGITALIS SULPHONATE DERIVATIVES OF DIFFERENT LIPOPHILICITY

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Metathetical Reactions of Silver Salts in Solution. II. The Synthesis of Alkyl Sulfonates1

Cited by 70 publications

References 0 publications

Improved synthesis of [18F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations

Improved synthesis of [18F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations

DNA interstrand crosslinking and sequence selectivity of dimethanesulphonates

ACTIVE SITE‐DIRECTED ALKYLATION OF Na+‐K+‐ATPase BY DIGITALIS SULPHONATE DERIVATIVES OF DIFFERENT LIPOPHILICITY

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Metathetical Reactions of Silver Salts in Solution. II. The Synthesis of Alkyl Sulfonates¹

Improved synthesis of [¹⁸F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations

Improved synthesis of [¹⁸F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations

ACTIVE SITE‐DIRECTED ALKYLATION OF Na⁺‐K⁺‐ATPase BY DIGITALIS SULPHONATE DERIVATIVES OF DIFFERENT LIPOPHILICITY