Compositions and methods to prevent toxicity induced by nonsteroidal antiinflammatory drugs
a non-steroidal anti-inflammatory drug and composition technology, applied in the direction of drug compositions, peptides, peptides, etc., can solve the problems of incompatibility of starting materials with substituents, toxic to cells, and irritation of salicylic acid itsel
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example 2
N—(N-L-γ-glutamyl-S-Nitroso-L-cysteinyl)glycine
[0109] N—(N-L-γ-glutamyl-L-cysteinyl)glycine (100 g, 0.325 mol) was dissolved in deoxygenated water (200 ml) and 2N HCl (162 ml) at room temperature and then the reaction mixture was cooled to 0° C. With rapid stirring, a solution of sodium nitrite (24.4 g, 0.35 mol) in water (40 ml) was added and stirring with cooling of the reaction mixture was continued for approximately 1 hour after which time the pink precipitate which formed was collected by vacuum filtration. The filter cake was resuspended in chilled 40% acetone-water (600 ml). and collected by vacumm filtration. The filter cake was washed with acetone (2×200 ml) and ether (100 ml) and then dried under high vacuum at room temperature in the dark to afford the title compound as a pink powder. 1H NMR (D2O) δ: 1.98 (m, 2H), 2.32 (t,2H), 3.67 (t, 1H), 3.82 (s 2H), 3.86 (dd, 1H), 3.98 (dd, 1H), 4.53 (m, 1H).
example 3
S-Nitroso-triphenylmethanethiol
[0110] Triphenylmethyl mercaptan (0.050 g, 0.18 mmol) was dissolved in anhydrous methylene chloride and cooled to 0° C. Tert-butyl nitrite (0.186 g, 1.80 mmol) was added and the resulting mixture was stirred at 0° C. for 30 min. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 1 hour. The solvent and excess of tert-butyl nitrite were evaporated to give the title compound as a green solid (0.054 g, 98%). 1H NMR (CDCl3) δ: 7.13-7.18 (m, 4 H), 7.25-7.39 (m, 11␣H).
example 4
4-O-Nitroso-1-(3-benzoyl-α-methylbenzeneacetic acid)butyl ester
4a. 4-Hydroxy-1-(3-benzoyl-α-methylbenzeneacetic acid)butyl ester
[0111] 3-Benzoyl-1-methylbenzeneacetic acid (4 g, 16 mmol) and 100 μL DMF were dissolved in benzene (25 mL). Oxalyl chloride (1.6 mL, 18 mmol) was added dropwise. Stirring was continued for 2 hr before concentration to a syrup. Butanediol (9 mL, 100 mmol) and pyridine (1.67 mL, 21 mmol) were dissolved in CH2Cl2 (100 mL) and dioxane (15 mL) and cooled to 0° C. A solution of the acid chloride was added in CH2Cl2 (20 mL). The reaction mixture was stirred cold for 20 min then warmed to room temperature with stirring for 2 hr. The solution was washed 1×30 H2O, 1 N HCl, satd NaHCO3 and brine; dried over Na2SO4; and the volatiles were evaporated. The residue was filtered through a pad of silica gel eluting with 2:1 Hex:EtOAc to yield 4.8 g (91%).of hydroxy ester. 1H NMR (CDCl3) δ: 7.41-7.81 (mult, 9H), 4.08-4.15 (mult, 2H), 3.79 (q, J=7.2 Hz, 1H), 3.59 (t, J=6.3...
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