N-hydroxy-2-(alkyl, aryl or heteroaryl sulfanyl, sulfinyl or sulfonyl-3-substituted-alkyl, aryl or heteroarylamides) as matrix metallo protein inhibitors
A technology of heteroaryl and alkyl, applied in the direction of active ingredients of amides, anti-inflammatory agents, metabolic diseases, etc., can solve problems such as bioavailability and pharmacokinetics, limit clinical effects, etc.
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Embodiment 1
[0111] N-Hydroxy-2-(4-methoxy-phenylsulfanyl)-2-methyl-3-phenyl-propionamide
[0112] To a stirred solution of 4-methoxybenzenethiol (2.8 g, 20 mmol) and anhydrous potassium carbonate (10 g, excess) in anhydrous acetone (100 mL) in a round bottom flask was added 2-bromo-propionic acid Ethyl ester (3.6 g, 20 mmol), and the reaction mixture was heated at reflux for 8 hours with good stirring. Finally, the reaction was cooled and the potassium salt was filtered off, and the above reaction mixture was concentrated. The residue was extracted with chloroform and washed with water and 0.5N sodium hydroxide solution. The organic layer was further washed extensively with water, dried over magnesium sulfate, filtered and concentrated to give ethyl 2-(4-methoxy-phenylsulfanyl)-propionate as a light yellow oil. Yield 4.5 g (94%); MS; 241 (M+H) + .
[0113] To a stirred solution of ethyl 2-(4-methoxy-phenylsulfanyl)-propionate (2.44 g, 10 mmol) in THF (100 ml) at -4°C, slowly add b...
Embodiment 2
[0117] N-Hydroxy-2-(4-methoxy-phenylsulfanyl)-2-phenyl-acetamide
[0118] Ethyl 2-(4-methoxyphenylsulfanyl)-phenylacetate was prepared according to the general procedure described in Example 1. Starting from ethyl α-bromophenylacetate (7.18 g, 31.4 mmol) and 4-methoxythiophenol (4.4 g, 31.4 mmol), 8 was isolated as a pale yellow oil. 5 g of product. Yield 90%; MS: 303.1 (M+H) + .
[0119] First, 2-(4-methoxy-phenylsulfanyl)-phenyl-acetic acid ethyl ester (3.0 g, 10 mmol) was dissolved in methanol (50 ml) and 10N sodium hydroxide (20 ml) to prepare 2- (4-Methoxy-phenylsulfanyl)-2-phenylacetic acid. The resulting reaction mixture was worked up as in Example 1. Yield 1.9 g, 70%. Low melting solid. MS: 273(M+H) + .
[0120] Using 2-(4-methoxy-phenylsulfanyl)-2-phenylacetic acid (1.05 g, 3.83 mmol) as raw material, according to the method described in the examples, 154 mg of N was isolated as a colorless solid. -Hydroxy-2-(4-methoxy-phenylsulfanyl)-2-phenyl-acetam...
Embodiment 3
[0122] 2-(4-Methoxy-phenylsulfanyl)-2,5-dimethyl-hex-4-enoic acid hydroxyamide
[0123] According to the method in the second paragraph of Example 1, 2-(4-methoxy-phenylsulfanyl)-2,5-dimethyl-hex-4-enoic acid ethyl ester was prepared. Using ethyl (4-methoxy-phenylsulfanyl)-propionate (3.5 g, 14.3 mmol) and isoprene bromide (2.25 g, 15 mmol) as starting materials, 2.2 g of The product of an oily substance. Yield 50%; MS: 310(M+H) + .
[0124] First, ethyl 2-(4-methoxy-phenylsulfanyl)-2,5-dimethyl-hex-4-enoate (2.0 g, 6.4 mmol) was dissolved in methanol (50 ml) and 2-(4-Methoxy-phenylsulfanyl)-2,5-dimethyl-hex-4-enoic acid was prepared in 10N sodium hydroxide (20ml). The resulting reaction mixture was worked up as described in Example 1. Yield of low melting solid was 1.9 g, 99%. MS: 280(M+H) + .
[0125] Using 2-(4-methoxy-phenylsulfanyl)-2,5-dimethyl-hex-4-enoic acid (1.67g, 5.8mmol) as raw material, according to the method described in the examples, 1.5 g of 2-(4...
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