The Oxidation of Tetronic Acids. Ii. Absence of Rearrangement in the Neopentyl System During Decarboxylation

Reid, Evans B.; Fortenbaugh, Robert B.

doi:10.1021/jo01141a005

J. Org. Chem.

1951

DOI: 10.1021/jo01141a005

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The Oxidation of Tetronic Acids. Ii. Absence of Rearrangement in the Neopentyl System During Decarboxylation

Evans B. Reid¹,

Robert B. Fortenbaugh²

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1997

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Cited by 10 publications

References 18 publications

(25 reference statements)

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Gerinnungsphysiologische Aktivität von 3,5‐disubstituierten Tetronsäuren

Rehse

Wagenknecht

Rietbrock

1978

Archiv der Pharmazie

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Rehse, Wagenknecht und RietbrockArch Pharm. CIOHI3N (147,2). IR (Film): 3300 (=CH), 2120 (C=C), 1615 (C=N), 1580 ( O C ) cm''. W (MeOH): hmax(log E ) = 263 (s, 4,30), 253 nm (4,39). MS (70 eV): m/e (rel. Int.) = 147 (69 %M+), 146 (29 7% M+-H), 132 (88 % M+-CH3), 117 (21 %, 132-CH3), 91 (100 %, M+-C4Hs). NMR: 6 (ppm) = 1,11 (s, 6H, CH3), 2,39-2,53 (m, 2H, C-3'), 3,23 (d, lH, J = 2Hz, C-l), 3,71-3,79 (m, 2H, C-5') 5,93,6,91 (AB-System, 2H, JAB = 16Hz, A-Teil aufgespalten zum d, J = 2Hz, C-3, c-4 1. Die ersten Tetronsiiuren mit blutgerinnungshemmender Wirkung werden beschrieben. Nach einmaliger oraler Verabreichung an Ratten (60-340 mg/kg) sank die Gerinnungsfihigkeit des Blutes (Quick-Zeit) auf weniger als 25 % der Norm. Diese Werte wurden bereits nach 8-15 h erreicht.Die Wirksamkeit hangt von der Art der Substituenten in 3und 5-Position der Tetronsaure ab. DieBeziehungen zwischen chemischer Struktur und biologischer Wirkung werden diskutiert. Anticoagulant Activity of 3,s-Disubstituted Tetronic AcidsThe first tetronic acids with anticoagulant activity are described. Eight to 15 h after oral administration of a single dose (60-340 mg/kg) to rats prothrombin levels < 25 %were observed. The activity strongly depends o n the nature of the substituents at positions 3 and 5 of the parent molecule. Structure-activity relationships are discussed.Fiir Tetronsaurederivate sind bereits mannigfache pharmakologische Aktivitaten beschrieben worden. Das Spektrum reicht von a~~tibakteriellenl-~) und insektiziden4) +) Auszug aus der Dissertation

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Gerinnungsphysiologische Aktivität von 3,5‐disubstituierten Tetronsäuren

Rehse

Wagenknecht

Rietbrock

1978

Archiv der Pharmazie

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Die Acyloin-Kondensation von 1,2-Diacyloxyethanen; Gezielte Darstellung unsymmetrisch substituierter 1,2-Bis-(trimethylsiloxy)ethene

1995

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Acyloin Condensation of 1,2‐Diacyloxyethanes; Directed Synthesis of Unsymmetrically Substituted 1,2‐Bis‐(trimethylsiloxy)ethenes A synthesis specifically directed to unsymmetrically substituted 1,2‐bis‐(trimethylsiloxy)ethenes (2a–d), precursors of the corresponding acyloins, was accomplished by intramolecular acyloin condensation of the unsymmetrical 1,2‐diacyloxyethanes (1a–d) with sodium in toluene/chlorotrimethylsilane.

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Hydroxyl Radical Mediates Nϵ-(Carboxymethyl)lysine Formation from Amadori Product

Nagai

Ikeda

Higashi

et al. 1997

Biochemical and Biophysical Research Communications

169

111

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The Oxidation of Tetronic Acids. Ii. Absence of Rearrangement in the Neopentyl System During Decarboxylation

Cited by 10 publications

References 18 publications

Gerinnungsphysiologische Aktivität von 3,5‐disubstituierten Tetronsäuren

Gerinnungsphysiologische Aktivität von 3,5‐disubstituierten Tetronsäuren

Die Acyloin-Kondensation von 1,2-Diacyloxyethanen; Gezielte Darstellung unsymmetrisch substituierter 1,2-Bis-(trimethylsiloxy)ethene

Hydroxyl Radical Mediates Nϵ-(Carboxymethyl)lysine Formation from Amadori Product

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