1,2,4-Oxadiazolylpyridinium salts. Oral hypoglycemic agents

Fanshawe, William J.; Bauer, V.; Safir, S. R.; Blickens, D. A.; Riggi, S. J.

doi:10.1021/jm00303a009

Cited by 12 publications

(9 citation statements)

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“…(18) J. T. Miner, G. E. Hawkins, C. A. Vanderwerf, A. Roe, J. Amer. VII, 16-18).-The cyanoacetate intermediate, 6, was added to a warm slurry of 15% Ba(OH)z in H20, and the reaction mixt was heated at 70°with stirring for 3 days. Periodically, during the course of the reaction, aliquots were removed from the reaction mixture and the uv spectra determined to insure that hydrolysis of the F substituent was not occurring.…”

Section: -Fluoro-3-bromomethylpyridine •Hbr (Tablementioning

confidence: 99%

“…The Growth media are described in Experimental Section. 6 No observable growth inhibition at the max level tested (600 Mg/ ml). = 40-80 % inhibition at 600 Mg/ml.…”

mentioning

confidence: 95%

“…Virtually complete growth inhibition occurs at " Incubated 36 hr at 30°. 6 Growth media was ; supplemented with 0,04 Mg/'nil of phenylalanine.…”

mentioning

confidence: 99%

“…There seems to be no apparent explanation for " Incubated 30 hr at 30°. 6 Growth media described in Fxperimental Section. the complete lack of toxicity of 17 in E. coli. p-Fluorophenylalanine, isosteric to 17, was reported by Berg-mann14 to inhibit completely the growth of E. coli (ATCC 9637) at an inhibitor concentration of 60 /ug/ml.…”

mentioning

confidence: 99%

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.alpha.-Fluoro- and .alpha.-hydroxypyridylalanines

Pt¹,

Cb²,

Sj³

1971

J. Med. Chem.

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Section: -Fluoro-3-bromomethylpyridine •Hbr (Tablementioning

confidence: 99%

“…The Growth media are described in Experimental Section. 6 No observable growth inhibition at the max level tested (600 Mg/ ml). = 40-80 % inhibition at 600 Mg/ml.…”

mentioning

confidence: 95%

“…Virtually complete growth inhibition occurs at " Incubated 36 hr at 30°. 6 Growth media was ; supplemented with 0,04 Mg/'nil of phenylalanine.…”

mentioning

confidence: 99%

mentioning

confidence: 99%

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.alpha.-Fluoro- and .alpha.-hydroxypyridylalanines

Pt¹,

Cb²,

Sj³

1971

J. Med. Chem.

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“…4-(4,5-Dimethyl-2-thiazolyl)pyridine (5).-A mixture of 5 g (0.036 mol) of thioisonicotinamide, 8.8 g (0.058 mol) of 3-bromo-2-butanone, and 50 ml of EtOH was heated under reflux for 6 hr and concentrated under reduced pressure to dryness. A suspension of the solid residue in 50 ml of H20 was made alkaline (1 X XaOH) and extracted (CHCls).…”

Section: Experimental Section16mentioning

confidence: 99%

Quaternary thiazolylpyridinium salts. Oral hypoglycemic agents

Wiegand¹,

Bauer²,

Safir³

et al. 1969

J. Med. Chem.

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Hypoglycemic Thiazolylpyridinium Salts 891give colorless needles of 9, mp 73-74°, nmr consistent. Anal.(C4H,ClaNS) C, , N, S.2,2-Dimethylthiazolidine Hydrochloride (10).-Thiol 1 (16.84 g, 148 mmoles) was dissolved in MeOH (25 ml) and excess Me2-CO (300 ml), and the mixture was heated under reflux for 8.5 hr. Evaporation of solvent gave a residue (20.3 g), mp 162-166°, which was crystallized three times from MeOH by addition of Et20 to give 10 as colorless needles (8.6 g, 38%), having constant mp 170-171.5°( lit.50 164-165°). Anal. (C6H12C1NS) C, H, S.2-Benzoylthiazolidine Hydrochloride (11).-Thiol 1 (5.50 g, 48.5 mmoles) and phenylglyoxal hydrate (7.60 g, 50 mmoles) were heated together at ca. 85°for ca. 5 min; the mixture then was dissolved in MeOH (30 ml) and Et20 (120 ml) was added to incipient turbidity. Cooling gave colorless 11 (4.4 g, 39%), mp 151-153°dec. Recrystallization three times from MeOH by addition of Et20 gave 11 with a melting point of 151.5-152.5°d ec, nmr consistent. Anal. (CioHi2C1NOS) C, , N, S.Spiro [2,3-dihydroindole-3,2'-thiazolidine] -2-one Hydrochloride (12).-Finely powdered isatin (10.95 g, 75 mmoles) was slowly added to thiol 1 (8.5 g, 75 mmoles) in f-PrOH (80 ml) to give a red mixture which, after being stirred for 24 hr at ca. 25°, became pale brown. Filtration separated pale brown 12 (15.4 g, 85%), mp 200-203°dec. A sample was recrystallized three times from MeOH by addition of Et20 and had a constant melting point of 203-204°d ec; ir (KBr), 2370, 1735 (amide C=0) cm-1. Anal. (CioHuCINiOS) C, , N, S. D-5,5-Dimethylthiazolidine-4-carboxylic Acid (13).-n-Penicillamine (35 g, 235 mmoles)10 was dissolved in 45% aqueous HCHO (200 ml, 3.0 moles). Within ca. 5 min, solid started to separate. The mixture was stirred for ca. 20 hr. Filtration then removed the colorless intermediate 14 (29 g, 69%), mp 111-112°, after a wash with dioxane then Et20 and drying over silica gel; ir

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Quaternary Pyridinium Compounds

Rodig¹

1974

Chemistry of Heterocyclic Compounds: A Series of Monographs

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1,2,4-Oxadiazolylpyridinium salts. Oral hypoglycemic agents

Cited by 12 publications

References 0 publications

.alpha.-Fluoro- and .alpha.-hydroxypyridylalanines

.alpha.-Fluoro- and .alpha.-hydroxypyridylalanines

Quaternary thiazolylpyridinium salts. Oral hypoglycemic agents

Quaternary Pyridinium Compounds

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