- 【药物名称】Netilmicin sulfate, Sch-20569, Certomycin, Zetamicin, Netillin, Netromicine, Netromycin
- 【化学名】O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1--6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1--4)]-2-deoxy-N1-ethyl-D-streptamine sulfate (2:5)
- 【CAS登记号】56391-57-2, 56391-56-1 (free base)
- 【结构式】
- 【分子式】2-C21-H41-N5-O7.5-H2-O4-S
- 【分子量】1441.555
- 【原研厂家】Schering-Plough (Originator), Essex (Not Determined), Menarini (Licensee)
- 【作用类别】Antibacterial Drugs, ANTIINFECTIVE THERAPY
- 【研发状态】Launched-1981
- 【合成情况】
- 〖来源〗J Chem Soc Chem Commun
- 〖合成路线〗
- 〖标题〗Synthesis of 1-N-ethylsisomicin: a broad-spectrum semisynthetic aminoglycoside antibiotic
- 〖合成方法〗By alkylation of sisomicin (I) with acetaldehyde (II) and sodium cyanoborohydride in water with some sulfuric acid.
- 〖作者〗Wright, J.J.
- 〖参考〗Wright, J.J.; Synthesis of 1-N-ethylsisomicin: a broad-spectrum semisynthetic aminoglycoside antibiotic. J Chem Soc Chem Commun 1976, 6, 206-208
- 〖出处〗J Chem Soc Chem Commun1976,,(6):206-208
- 〖备注〗
- 〖来源〗Drugs Fut
- 〖合成路线〗
- 〖标题〗Netilmicin
- 〖合成方法〗By alkylation of sisomicin (I) with acetaldehyde (II) and sodium cyanoborohydride in water with some sulfuric acid.
- 〖作者〗Castaer, J.; Loren, J.G.
- 〖参考〗Castaer, J.; Loren, J.G.; Netilmicin. Drugs Fut 1978, 3, 7, 527
- 〖出处〗Drugs Fut1978,3,(7):527
- 〖备注〗Synthesis By alkylation of sisomicin (I) with acetaldehyde (II) and sodium cyanoborohydride in water with some sulfuric acid (1,2). Description [alpha](26 C)(D) = +164. Manufacturer Schering Corp (USA) References 1. Weinstein, M.J. et al (Scherico Ltd.); BE 818431, FR 2240015, DE 2437160, JP 7547951, NL 7410363, ZA 7404939 2. Wright, J.J.; Synthesis of 1-N-ethylsisomicin: a broad-spectrum semisynthetic aminoglycoside antibiotic; J Chem Soc Chem Commun 1976, (6), 206-208
- 〖来源〗Org Process Res Dev
- 〖合成路线〗
- 〖标题〗An efficient and selective 1-N-monoethylation of sisomicin: Process development of netilmicin
- 〖合成方法〗The selective triacetylation of sisomicin (I) with zinc acetate, acetic anhydride and TEA in methanol/THF gives the triacetate (II), which is then alkylated with acetic acid and NaBH4 in chloroform, affording 1-N-ethyl-3,2',6'-tri-N-acetylsisomicin (III). Finally, this compound is deacetylated by means of refluxing aqueous NaOH.
- 〖作者〗Nam, G.; et al.
- 〖参考〗Nam, G.; et al.; An efficient and selective 1-N-monoethylation of sisomicin: Process development of netilmicin. Org Process Res Dev 2002, 6, 1, 78
- 〖出处〗Org Process Res Dev2002,6,(1):78
- 〖备注〗
- 〖来源〗DE 2437160; FR 2240015; GB 1473733; US 4029882
- 〖合成路线〗
- 〖标题〗Novel pseudotrisaccharides and methods for their production
- 〖合成方法〗By alkylation of sisomicin (I) with acetaldehyde (II) and sodium cyanoborohydride in water with some sulfuric acid.
- 〖作者〗Daniels, P.J.L.; Testa, R.; Tattanahalli, L.; Mallams, A.K.; Wright, J.J.; Weinstein, M.J.; Wagman, G.H. (Schering Corp.)
- 〖参考〗Daniels, P.J.L.; Testa, R.; Tattanahalli, L.; Mallams, A.K.; Wright, J.J.; Weinstein, M.J.; Wagman, G.H. (Schering Corp.); Novel pseudotrisaccharides and methods for their production. DE 2437160; FR 2240015; GB 1473733; US 4029882
- 〖出处〗DE 2437160; FR 2240015; GB 1473733; US 4029882,,():
- 〖备注〗
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