Some Derivatives of Tetrahydrothiapyran as Possible Local Anesthetics

Barkenbus, Charles; Wuellner, James A.

doi:10.1021/ja01619a056

Cited by 5 publications

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“…2-Chloroethyl Tetrahydro-2H-thiopyran-4-caiba-mateS,5-Dioxide (2f). ClCO^CH^Cl (4.72 g, 33.0 mmoles) was added dropwise during 15-20 min to a stirred soln of lf-HCl (5.72 g, 30.8 mmoles) and NaOH (2.70 g, 67.5 mmoles) in , (100 ml) at ~25°. Stirring was contd 1 hr before the cryst 2f was collected and dried in vacuo (25°, P2Os).…”

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“…Na3PS03 (1.80 g, 10.0 mmoles) was dissolved in H20 (100 ml); EtOH (50 ml) and DMF (10 ml) were then added. Powd 6c ( = 3) was gradually added in portions during 15 min, the mixt being stirred until a clear soln was obtained (~4 hr). Cryst 13c sepd when the soln was poured into EtOH (400 ml) and, after refrign, was collected, washed with a small amt of cold HsO, and air-dried; yield 60% (2.65 g).Anal.…”

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N-Alicyclic-substituted derivatives of 2-aminoethanethiol and related compounds as antiradiation agents

Elliott¹,

Piper²,

Stringfellow³

et al. 1972

J. Med. Chem.

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A number of 2-aminoethanethiol derivatives, RNHfCH^SY, in which R is an alicyclic or heteroalicyclic group and SY is a suitable S function (e. g., thiol, thiosulfate, or phosphorothioate), were synthesized for evaluation as antiradiation agents. The intermediate N-substituted 2-bromoethylamines were prepared from either 3-substituted 2-oxazolidinones derived from primary amines or N-substituted 2-aminoethanols derived from cyclic ketones. The adaptability of the first approach to the synthesis of 3-aminopropanethiol derivatives was demonstrated. Eight of the 38 compounds tested in mice by ip administration showed

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