& MF-569, 3-IAABU,-4,C10-H10-I-N3-O3,N-[3-(Iodoacetam
MF-569, 3-IAABU,-4,C10-H10-I-N3-O3,N-[3-(Iodoacetam
摘 要：MF-569, 3-IAABU,-4,C10-H10-I-N3-O3,N-[3-(Iodoacetamido)benzoyl] N-Carbamoyl-3-(2-iodoacetamido)benzamide
【药物名称】MF-569, 3-IAABU
【化学名】N-[3-(Iodoacetamido)benzoyl] N-Carbamoyl-3-(2-iodoacetamido)benzamide
【CAS登记号】-4
【结构式】
【分子式】C10-H10-I-N3-O3
【分子量】347.107
【原研厂家】Cytoskeleton (Originator), Mount Sinai School of Medicine (Originator), New York University (Originator)
【作用类别】ONCOLYTIC DRUGS, Antimitotic Drugs, Microtubule-Stabilizing Agents
【研发状态】Biological Testing
【合成情况】　
〖来源〗Anti-Cancer Drug Des
〖合成路线〗
〖标题〗Synthesis, cancericidal and antimicrotubule activities of 3-(haloacetamido)-benzoylureas
〖合成方法〗The acylation of 3-aminobenzoic acid with acetic anhydride in ethyl acetate gives the corresponding acetamide (II), which is treated with SOCl2 in refluxing ethyl acetate yielding 3-(trifluoroacetamido)benzoyl chloride (III). The reaction of (III) with urea (IV) in toluene at 100 C gives the acylated urea (V), which is deprotected with butylamine in refluxing methanol to afford N-(3-aminobenzoyl)urea (VI). The acylation of (VI) with chloroacetyl chloride (VII) in dimethylacetamide provides the corresponding amide (VIII), which is finally treated with NaI in dimethylacetamide.
〖作者〗Bekesi, J.G.; Holland, J.F.; Jiang, J.-D.; Ma, L.; Roboz, J.; Deng, L.; Weisz, I.
〖参考〗Bekesi, J.G.; Holland, J.F.; Jiang, J.-D.; Ma, L.; Roboz, J.; Deng, L.; Weisz, I.; Synthesis, cancericidal and antimicrotubule activities of 3-(haloacetamido)-benzoylureas. Anti-Cancer Drug Des , 735
〖出处〗Anti-Cancer Drug Des):735
〖备注〗The acylation of 3-aminobenzoic acid with acetic anhydride in ethyl acetate gives the corresponding acetamide (II), which is treated with SOCl2 in refluxing ethyl acetate yielding 3-(trifluoroacetamido)benzoyl chloride (III). The reaction of (III) with urea (IV) in toluene at 100?gives the acylated urea (V), which is deprotected with butylamine in refluxing methanol to afford N-(3-aminobenzoyl)urea (VI). The acylation of (VI) with chloroacetyl chloride (VII) in dimethylacetamide provides the corresponding amide (VIII), which is finally treated with NaI in dimethylacetamide.
本文导航：
MF-569, 3-IAABU,-4,C10-H10-I-N3-O3,N-[3-(Iodoacetam
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你可能喜欢& ,C12H21NO9,323.3025,methyl (2S,4S,5R,6R)-5-(acetam
,C12H21NO9,323.3025,methyl (2S,4S,5R,6R)-5-(acetam
摘 要：,C12H21NO9,323.3025,methyl (2S,4S,5R,6R)-5-(acetamido)-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydro-2H-pyran-2-carboxylate
【化学名】methyl (2S,4S,5R,6R)-5-(acetamido)-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydro-2H-pyran-2-carboxylate
【CAS登记号】
【结构式】
【分子式】C12H21NO9
【分子量】323.3025
【来源】Toronto Research Chemicals, Inc.
【合成情况】　
〖目标产物〗Zanamivir, GR-121167X(former code), GG-167, 4-Guanidino-Neu5Ac2en, Relenza
〖合成路线〗
〖合成方法〗1) The esterification of N-acetylneuraminic acid (I) with methanol/HCl gives the corresponding methyl ester (II), which is acetylated with acetic anhydride, pyridine and dimethylaminopyridine (DMAP) yielding the pentaacetate (III). The reaction of (III) with trimethylsilyl trifluoromethanesulfonate in ethyl acetate affords the 2,3-didehydro derivative (IV), which is treated with trimethylsilyl azide in butanol to give the 4-azido derivative (V). The selective deacetylation of (V) with sodium methoxide in methanol yields N-acetyl-4-azido-2,4-dideoxy-2,3-didehydroneuraminic acid methyl ester (VI), which is reduced with H2 over Lindlar catalyst (Pd-Pb) in water and treated with Dowex 8x2 resin to afford the N-acetyl-4-amino-2,4-dideoxy-2,3-didehydroneuraminic acid (VII). The reaction of (VII) with BrCN and sodium acetate in methanol gives the corresponding 4-cyanoamino derivative (VIII), which is converted into the final product by reaction with ammonium formate in aqueous NH4OH.
2) The amino derivative (VII) can be converted directly into the final product by reaction with amidinosulfonic acid (X), NaOH and K2CO3 in water.
3) The amino derivative (VII) can also be converted directly into the final product by reaction with pyrazole-1-carboxamidine (XI) and triethylamine in water.
〖参考〗von Itzstein, M.; Wu, W.-Y.; Jin, B.; The synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid: A potent influenza virus sialidase inhibitor. Carbohydr Res , 2, 301-5
〖目标产物〗Zanamivir, GR-121167X(former code), GG-167, 4-Guanidino-Neu5Ac2en, Relenza
〖合成路线〗
〖合成方法〗1) The esterification of N-acetylneuraminic acid (I) with methanol/HCl gives the corresponding methyl ester (II), which is acetylated with acetic anhydride, pyridine and dimethylaminopyridine (DMAP) yielding the pentaacetate (III). The reaction of (III) with trimethylsilyl trifluoromethanesulfonate in ethyl acetate affords the 2,3-didehydro derivative (IV), which is treated with trimethylsilyl azide in butanol to give the 4-azido derivative (V). The selective deacetylation of (V) with sodium methoxide in methanol yields N-acetyl-4-azido-2,4-dideoxy-2,3-didehydroneuraminic acid methyl ester (VI), which is reduced with H2 over Lindlar catalyst (Pd-Pb) in water and treated with Dowex 8x2 resin to afford the N-acetyl-4-amino-2,4-dideoxy-2,3-didehydroneuraminic acid (VII). The reaction of (VII) with BrCN and sodium acetate in methanol gives the corresponding 4-cyanoamino derivative (VIII), which is converted into the final product by reaction with ammonium formate in aqueous NH4OH.
2) The amino derivative (VII) can be converted directly into the final product by reaction with amidinosulfonic acid (X), NaOH and K2CO3 in water.
3) The amino derivative (VII) can also be converted directly into the final product by reaction with pyrazole-1-carboxamidine (XI) and triethylamine in water.
〖参考〗Chandler, M.; Bamford, M.J.; Conroy, R.; et al.; Synthesis of the potent influenza neuraminidase inhibitor 4-guanidino Neu5Ac2en. X-Ray molecular structure of 5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-erythro-L-gluco-nononic acid. J Chem Soc - Perki>span>【CAS登记号】/span>/li>
〖目标产物〗Zanamivir, GR-121167X(former code), GG-167, 4-Guanidino-Neu5Ac2en, Relenza
〖合成路线〗
〖合成方法〗1) The esterification of N-acetylneuraminic acid (I) with methanol/HCl gives the corresponding methyl ester (II), which is acetylated with acetic anhydride, pyridine and dimethylaminopyridine (DMAP) yielding the pentaacetate (III). The reaction of (III) with trimethylsilyl trifluoromethanesulfonate in ethyl acetate affords the 2,3-didehydro derivative (IV), which is treated with trimethylsilyl azide in butanol to give the 4-azido derivative (V). The selective deacetylation of (V) with sodium methoxide in methanol yields N-acetyl-4-azido-2,4-dideoxy-2,3-didehydroneuraminic acid methyl ester (VI), which is reduced with H2 over Lindlar catalyst (Pd-Pb) in water and treated with Dowex 8x2 resin to afford the N-acetyl-4-amino-2,4-dideoxy-2,3-didehydroneuraminic acid (VII). The reaction of (VII) with BrCN and sodium acetate in methanol gives the corresponding 4-cyanoamino derivative (VIII), which is converted into the final product by reaction with ammonium formate in aqueous NH4OH.
2) The amino derivative (VII) can be converted directly into the final product by reaction with amidinosulfonic acid (X), NaOH and K2CO3 in water.
3) The amino derivative (VII) can also be converted directly into the final product by reaction with pyrazole-1-carboxamidine (XI) and triethylamine in water.
〖参考〗Fromtling, R.; Castaer, J.; Zanamivir. Drugs Fut , 375
〖目标产物〗Zanamivir, GR-121167X(former code), GG-167, 4-Guanidino-Neu5Ac2en, Relenza
〖合成路线〗
〖合成方法〗1) The esterification of N-acetylneuraminic acid (I) with methanol/HCl gives the corresponding methyl ester (II), which is acetylated with acetic anhydride, pyridine and dimethylaminopyridine (DMAP) yielding the pentaacetate (III). The reaction of (III) with trimethylsilyl trifluoromethanesulfonate in ethyl acetate affords the 2,3-didehydro derivative (IV), which is treated with trimethylsilyl azide in butanol to give the 4-azido derivative (V). The selective deacetylation of (V) with sodium methoxide in methanol yields N-acetyl-4-azido-2,4-dideoxy-2,3-didehydroneuraminic acid methyl ester (VI), which is reduced with H2 over Lindlar catalyst (Pd-Pb) in water and treated with Dowex 8x2 resin to afford the N-acetyl-4-amino-2,4-dideoxy-2,3-didehydroneuraminic acid (VII). The reaction of (VII) with BrCN and sodium acetate in methanol gives the corresponding 4-cyanoamino derivative (VIII), which is converted into the final product by reaction with ammonium formate in aqueous NH4OH.
2) The amino derivative (VII) can be converted directly into the final product by reaction with amidinosulfonic acid (X), NaOH and K2CO3 in water.
3) The amino derivative (VII) can also be converted directly into the final product by reaction with pyrazole-1-carboxamidine (XI) and triethylamine in water.
〖参考〗Weir, N.G.; Chandler, M.; Bamford, M.J. (Glaxo Wellcome plc); Synthesis of N-acetyl neuraminic acid derivs. WO 9407885
〖目标产物〗Zanamivir, GR-121167X(former code), GG-167, 4-Guanidino-Neu5Ac2en, Relenza
〖合成路线〗
〖合成方法〗1) The esterification of N-acetylneuraminic acid (I) with methanol/HCl gives the corresponding methyl ester (II), which is acetylated with acetic anhydride, pyridine and dimethylaminopyridine (DMAP) yielding the pentaacetate (III). The reaction of (III) with trimethylsilyl trifluoromethanesulfonate in ethyl acetate affords the 2,3-didehydro derivative (IV), which is treated with trimethylsilyl azide in butanol to give the 4-azido derivative (V). The selective deacetylation of (V) with sodium methoxide in methanol yields N-acetyl-4-azido-2,4-dideoxy-2,3-didehydroneuraminic acid methyl ester (VI), which is reduced with H2 over Lindlar catalyst (Pd-Pb) in water and treated with Dowex 8x2 resin to afford the N-acetyl-4-amino-2,4-dideoxy-2,3-didehydroneuraminic acid (VII). The reaction of (VII) with BrCN and sodium acetate in methanol gives the corresponding 4-cyanoamino derivative (VIII), which is converted into the final product by reaction with ammonium formate in aqueous NH4OH.
2) The amino derivative (VII) can be converted directly into the final product by reaction with amidinosulfonic acid (X), NaOH and K2CO3 in water.
3) The amino derivative (VII) can also be converted directly into the final product by reaction with pyrazole-1-carboxamidine (XI) and triethylamine in water.
〖参考〗Patel, V. (Glaxo Wellcome plc); Synthesis of N-acetyl neuraminic acid derivs. WO 9407886
〖目标产物〗Zanamivir, GR-121167X(former code), GG-167, 4-Guanidino-Neu5Ac2en, Relenza
〖合成路线〗
〖合成方法〗1) The esterification of N-acetylneuraminic acid (I) with methanol/HCl gives the corresponding methyl ester (II), which is acetylated with acetic anhydride, pyridine and dimethylaminopyridine (DMAP) yielding the pentaacetate (III). The reaction of (III) with trimethylsilyl trifluoromethanesulfonate in ethyl acetate affords the 2,3-didehydro derivative (IV), which is treated with trimethylsilyl azide in butanol to give the 4-azido derivative (V). The selective deacetylation of (V) with sodium methoxide in methanol yields N-acetyl-4-azido-2,4-dideoxy-2,3-didehydroneuraminic acid methyl ester (VI), which is reduced with H2 over Lindlar catalyst (Pd-Pb) in water and treated with Dowex 8x2 resin to afford the N-acetyl-4-amino-2,4-dideoxy-2,3-didehydroneuraminic acid (VII). The reaction of (VII) with BrCN and sodium acetate in methanol gives the corresponding 4-cyanoamino derivative (VIII), which is converted into the final product by reaction with ammonium formate in aqueous NH4OH.
2) The amino derivative (VII) can be converted directly into the final product by reaction with amidinosulfonic acid (X), NaOH and K2CO3 in water.
3) The amino derivative (VII) can also be converted directly into the final product by reaction with pyrazole-1-carboxamidine (XI) and triethylamine in water.
〖参考〗Chandler, M.; Weir, N. (Glaxo Wellcome plc); Preparation of N-acetyl neuraminic derivs. WO 9312105
本文导航：
,C12H21NO9,323.3025,methyl (2S,4S,5R,6R)-5-(acetam
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