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/protein ingredients, etc., can solve the problems of potentially toxic to cells, irritating salicylic acid itself, and only being used externally
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example 2
N—(N-L-γ-glutamyl-S-Nitroso-L-cysteinyl)glycine
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
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, 4H), 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
3-Benzoyl-α-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 Hz, 2...
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