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【结 构 式】

【药物名称】SB-425076

【化学名称】2-[3-(6-Ethyl-8-iodo-1,2,3,4-tetrahydroquinolin-4-ylamino)propylamino]quinolin-4(1H)-one dihydrochloride

【CA登记号】263896-15-7

【 分 子 式 】C23H29Cl2IN4O

【 分 子 量 】575.32418

【开发单位】GlaxoSmithKline (Originator)

【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Methionyl-tRNA Synthetase Inhibitors

合成路线1

Condensation of 4-ethylaniline (I) with propiolactone (II) produces the beta-aminoacid (III). Intramolecular Friedel-Crafts cyclization of (III) by means of polyphosphoric acid leads to the quinolinone (IV). Then, electrophilic iodination of (IV) by using iodine monochloride provides the intermediate (V)

1 Jarvest, R.L.; Berge, J.M.; Berry, V.; et al.; Nanomolar inhibitors of Staphylococcus aureus methionyl tRNA synthetase with potent antibacterial activity against Gram-positive pathogens. J Med Chem 2002, 45, 10, 1959.
2 Berge, J.M.; Forrest, A.K.; Elder, J.S.; Jarvest, R.L. (GlaxoSmithKline plc); Quinolones as t-RNA synthetase inhibitors and antibacterial agents. WO 0021949 .
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) 60623 4-ethylaniline; 4-ethylphenylamine C8H11N 详情 详情
(II) 24477 2-oxetanone 57-57-8 C3H4O2 详情 详情
(III) 60624 3-(4-ethylanilino)propanoic acid C11H15NO2 详情 详情
(IV) 60625 6-ethyl-2,3-dihydro-4(1H)-quinolinone C11H13NO 详情 详情
(V) 60626 6-ethyl-8-iodo-2,3-dihydro-4(1H)-quinolinone C11H12INO 详情 详情

合成路线2

Displacement of 2-chloro-4-ethoxyquinoline (VI) with 1,3-propanediamine (VII) affords the aminoquinoline (VIII). Subsequent acidic hydrolysis of (VIII) provides quinolinone (IX). Finally, reductive condensation between amine (IX) and ketone (V) in the presence of NaBH3CN leads to the target disubstituted propanediamine

1 Jarvest, R.L.; Berge, J.M.; Berry, V.; et al.; Nanomolar inhibitors of Staphylococcus aureus methionyl tRNA synthetase with potent antibacterial activity against Gram-positive pathogens. J Med Chem 2002, 45, 10, 1959.
2 Berge, J.M.; Forrest, A.K.; Elder, J.S.; Jarvest, R.L. (GlaxoSmithKline plc); Quinolones as t-RNA synthetase inhibitors and antibacterial agents. WO 0021949 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 60626 6-ethyl-8-iodo-2,3-dihydro-4(1H)-quinolinone C11H12INO 详情 详情
(VI) 60627 2-chloro-4-ethoxyquinoline; 2-chloro-4-quinolinyl ethyl ether C11H10ClNO 详情 详情
(VII) 19331 3-aminopropylamine; 1,3-propanediamine 109-76-2 C3H10N2 详情 详情
(VIII) 60628 N-(3-aminopropyl)-N-(4-ethoxy-2-quinolinyl)amine; N~1~-(4-ethoxy-2-quinolinyl)-1,3-propanediamine C14H19N3O 详情 详情
(IX) 60629 2-[(3-aminopropyl)amino]-4(1H)-quinolinone C12H15N3O 详情 详情
Extended Information