SB-425076
Chemical Name: 2-[3-(6-Ethyl-8-iodo-1,2,3,4-tetrahydroquinolin-4-ylamino)propylamino]quinolin-4(1H)-one dihydrochloride
CAS No. 263896-15-7
项目整合开发状态: Preclinical
项目研究机构: GlaxoSmithKline (Originator)
合成路线: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)
合成路线: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
📌 参考资料/链接：
参考文献标题:Quinolones as t-RNA synthetase inhibitors and antibacterial agents
文献作者:Berge,J.M.; Forrest,A.K.; Elder,J.S.; Jarvest,R.L.(GlaxoSmithKline plc)
参考来源:WO 0021949
📄 详细内容
合成路线: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)
合成路线: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
参考文献标题:Nanomolar inhibitors of Staphylococcus aureus methionyl tRNA synthetase with potent antibacterial activity against Gram-positive pathogens
文献作者:Jarvest,R.L.; Berge,J.M.; Berry,V.; Boyd,H.F.; Brown,M.J.B.; Elder,J.S.; Forrest,A.K.; Fosberry,A.P.; Gentry,D.R.; Hibbs,M.J.; Jaworski,D.D.; O'Hanlon,P.J.; Pope,A.J.; Rittenhouse,S.; Sheppard,R.J.; Slater-Radosti,C.; Worby,A.
参考来源:J Med Chem 2002,45(10),1959