Gerinnungsphysiologische Aktivität von 3,5‐disubstituierten Tetronsäuren

Abstract

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

3-Methyl-1,4-diphenyl-1H,5H,7H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one

“…The pyrazolo [3,4-b]pyridine system has many interesting biological and pharmacological properties, such as antitubercular action and action against Gram-positive and Gramnegative bacteria, and it is used in the treatment of a wide variety of stress-related illnesses (Kuczynski et al, 1979). It is well known that tetronic acid derivatives are interesting because of their antibiotic (Ley et al, 1991), antitumour (Hata et al, 1993), anticoagulant (Rehse et al, 1978), anti-epileptic (Zhang et al, 1992), antifungal (Vishwakarma et al, 1987), insecticidal (Ibi et al, 1979) and analgesic (Dal Pozzo et al, 1974) properties. However, furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one derivatives, which contain both pyrazolo[3,4-b]pyri-]pyridine and tetronic acid fragments, have not received much attention.…”

Highly active magnetically separable CuFe2O4 nanocatalyst: an efficient catalyst for the green synthesis of tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H) dione derivatives

“…Tetronic acid (tetrahydrofuran-2,4-dione) is one of the important heterocyclic units, has a broad spectrum of biological properties such as antifungal [11], antibiotic [12][13][14][15][16], insecticidal [17], anticoagulant [18][19][20], antiepileptic [21], analgesic [22] and anti-inflammatory activities [23]. Podophyllotoxin ( Fig.…”

A Facile and Expeditious Microwave-Assisted Synthesis of Furo[3,4-b]indeno[2,1-f]quinolin-1-one DerivativesviaMulticomponent Reaction

“…Tetronic acid derivatives and their metabolites are interesting because of their antibiotic [3], anticoagulant [4], antiepileptic [5], antifungal [6], insecticidal [7], analgesic [8], anti‐inflammatory activities [9], and HIV‐1 (Human Immunodeficiency Virus) protease inhibitors [10]. In addition, the quinoline moiety is one of the significant core structures among the most extensively natural and unnatural heterocyclic compounds [11] with remarkable medicinal activities [12].…”