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【结 构 式】

【药物名称】MRS-1476

【化学名称】6-Ethyl-5-(ethylsulfanylcarbonyl)-2-phenyl-4-propylpyridine-3-carboxylic acid ethyl ester

【CA登记号】212329-36-7

【 分 子 式 】C21H25NO3S

【 分 子 量 】371.5023

【开发单位】National Institutes of Health (Originator)

【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Adenosine A3 Antagonists, Antiinflammatory Drugs

合成路线1

Acylation of Meldrum's acid (I) with propionyl chloride (II) in the presence of pyridine gave propionyl derivative (III). Subsequent ring opening of (III) with ethanethiol (IV), followed by decarboxylation provided S-ethyl 3-oxothiovalerate (V). Ethyl 3-amino-3-phenyl-2-propenoate (VII) was prepared by reaction of benzoylacetate (VI) with ammonium acetate in refluxing ethanol. Then, Hantzsch condensation of ketothioester (V), beta-enaminoester (VII), and propionaldehyde (VIII) in EtOH at 80 C in a sealed tube furnished the dihydropyridine (IX). Finally, oxidation of (IX) using chloranil (X) in boiling THF gave the target pyridine.

1 Li, A.-H.; Moro, S.; Melman, N.; Ji, X.D.; Jacobson, K.A.; Structure-activity relationships and molecular mod. J Med Chem 1998, 41, 17, 3186.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 14738 Meldrum's acid; 2,2-dimethyl-1,3-dioxane-4,6-dione;Malonic acid cyclic isopropylidene ester 2033-24-1 C6H8O4 详情 详情
(II) 15967 propanoyl chloride; propionyl chloride 79-03-8 C3H5ClO 详情 详情
(III) 23689 2,2-dimethyl-5-propionyl-1,3-dioxane-4,6-dione C9H12O5 详情 详情
(IV) 23712 1-ethanethiol; ethylhydrosulfide 75-08-1 C2H6S 详情 详情
(V) 23696 S-ethyl 3-oxopentanethioate C7H12O2S 详情 详情
(VI) 23692 propyl 3-oxo-3-phenylpropanoate C12H14O3 详情 详情
(VII) 23693 propyl (E)-3-amino-3-phenyl-2-propenoate C12H15NO2 详情 详情
(VIII) 15966 propionaldehyde 123-38-6 C3H6O 详情 详情
(IX) 23699 ethyl 4,6-diethyl-5-[(ethylsulfanyl)carbonyl]-2-phenyl-1,4-dihydro-3-pyridinecarboxylate C21H27NO3S 详情 详情
(X) 21891 2,3,5,6-Tetrachloro-1,4-benzoquinone; 2,3,5,6-Tetrachlorobenzo-1,4-quinone; p-Chloranil 118-75-2 C6Cl4O2 详情 详情
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