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阿贝卡星 | 51025-85-5

阿贝卡星结构式图片|51025-85-5结构式图片
阿贝卡星
Arbekacin
51025-85-5
C22H44N6O10
552.62
如需查看该化合物的详细结构式,mol文件,smile,InChi 请点击:阿贝卡星结构式
68682
简介
中文名称:阿贝卡星
英文名称:Arbekacin
英文别名:Arbekacin [INN]; Arbekacin; Arbekacina;Arbekacina [Spanish]; Arbekacine; Arbekacine [French]; Arbekacinum; Arbekacinum [Latin]; Haberacin;
CAS:51025-85-5
分子式:C22H44N6O10
分子量:552.619
名称和标识符
MDL MFCD00864919
InChIKey MKKYBZZTJQGVCD-XTCKQBCOSA-N
Inchi InChI=1S/C22H44N6O10/c23-4-3-12(30)20(34)28-11-5-10(26)18(37-21-9(25)2-1-8(6-24)35-21)17(33)19(11)38-22-16(32)14(27)15(31)13(7-29)36-22/h8-19,21-22,29-33H,1-7,23-27H2,(H,28,34)/t8-,9+,10-,11+,12-,13+,14-,15+,16+,17-,18+,19-,21+,22+/m0/s1
SMILES NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](NC([C@@H](O)CCN)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](N)[C@H](O)[C@H](O3)CO)[C@H]2O)[C@H](N)CC1
别名信息
- 中文别名 -
  • 阿贝卡星
  • (S)-O-3-氨基-3-脱氧-Α-D-葡糖吡喃糖基-(1→6)-O-[2,6-二氨基-2,3,4,6-四脱氧-Α-D-叠-六吡喃糖基-(1→4)-]-N^^(L-氨基-2-羟基-L-氧代丁基)-2-脱氧-D-链霉胺
- 英文别名 -
  • Arbekacin
  • Arbekacin [INN]
  • Arbekacina
  • Arbekacina [Spanish]
  • Arbekacine
  • Arbekacine [French]
  • Arbekacinum
  • Arbekacinum [Latin]
  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-ery
  • Haberacin
  • O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1-6))-N'-((2S)-4-amino-2-hydroxybutyryl)-2-deoxy-L-streptamine
  • (2S)-4-Amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2R,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-but
  • (2S)-4-Amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2R,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-butanamide
  • (S)-4-amino-N-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide
  • DB06696
  • G7V6SLI20L
  • CHEMBL426926
  • ME-1100
  • Arbekacin (INN)
  • MKKYBZZTJQGVCD-XTCKQBCOSA-N
  • O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1->6))-N'-((2S)-4-amino-2-hydroxybutyryl)-2-deoxy-L-streptamine
  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1-4))-N1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)-
  • 51025-85-5
  • GTPL7345
  • DKB-AHB
  • O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-ERYTHRO-HEXOPYRANOSYL-(1->6))-N'-((2S)-4-AMINO-2-HYDROXYBUTYRYL)-2-DEOXY-L-STREPTAMINE
  • NPC-14
  • D07462
  • D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-ERYTHRO-HEXOPYRANOSYL-(1->4))-N1-((2S)-4-AMINO-2-HYDROXY-1-OXOBUTYL)-2-DEOXY-
  • DTXSID8048319
  • SCHEMBL18413
  • CHEBI:37922
  • ARBEKACIN [MI]
  • ME1100
  • (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
  • UNII-G7V6SLI20L
  • (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-(3-amino-3-deoxy-alpha-D-glucopyranosyloxy)-4-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyloxy)-3-hydroxycyclohexyl]-2-hydroxybutanamide
  • NCGC00167530-01
  • 1665RB
  • AHB-DKB
  • Arbecacin
  • HABA-DKB
  • HBK
  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1-4))-N(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)-
  • Q4784668
  • (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
  • (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydropyran-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-butanamide
  • 51025-85-5 (free base)
  • (S)-4-amino-N-((1R,2S,3S,4R,5S)-5-amino-2-((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-4-((2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide
  • Butanamide, 4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-.alpha.-D-glucopyranosyl)oxy]-4-[(2,6-diamino-2,3,4,6-tetradeoxy-.alpha.-D-erythro-hexopyranosyl)oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (2S)-
  • AKOS025149466
  • ARBEKACIN [WHO-DD]
  • Arbekacin sulfate [JAN]
  • (2S)-4-amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-alpha-D-glucopyranosyl)oxy]-4-[(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide
  • 84G
物化性质
实验特性
LogP -2.50700
PSA 297.27
折射率 1.634
沸点 904 °C at 760 mmHg
闪点 904 °C at 760 mmHg
密度 1.47
计算特性
精确分子量 552.31212
氢键供体数量 11
氢键受体数量 16
可旋转化学键数量 11
同位素质量 552.312
重原子数量 38
复杂度 757
同位素原子数量 0
确定原子立构中心数量 14
不确定原子立构中心数量 0
确定化学键立构中心数量 0
不确定化学键立构中心数量 0
共价键单元数量 1
疏水参数计算参考值(XlogP) -6.8
拓扑分子极性表面积 297A^2
国际标准相关数据
EINECS None
生产方法和用途
方法
3’,4’-二脱氧卡那霉素B和等当量的叔丁氧羰基叠氮化物,在水、吡啶和三乙胺(10:10:1)的混合溶液中,在室温下反应18h。然后用Amberlite CG50(NH4+)柱层析,得6’-N-叔丁氧羰基-3’,4’-二脱氧卡那霉素B,收率49%,熔点136~140℃(分解),[α] {D}^26+112°(C=1.0,水)。同时回收36%未反应的3’,4’-二脱氧卡那霉素B。6’-N-叔丁氧羰基-3’,4’-二脱氧卡那霉素B(1.1g,2.0mmo1)和叔丁氧羰基叠氮化物(320mg,2.2mmo1)在和上述相同的条件下反应,得到1.41g黄色粉末。不用提纯,溶于20ml水和10ml二甲氧基乙烷,用(S)-4-叔丁氧羰基氨基-2-羟基丁酸(N-羟基丁二酰亚胺)酯(696mg,2.2mmo1)在10ml二甲氧基乙烷中的溶液,在室温下酰化20h。和10ml 90%三氟乙酸在室温下反应40min,移去叔丁氧羰基。反应液浓缩至于,用Amberlite CG50(NH4+)柱层析,用水和0.5mol/L氨水洗脱后,再用0.75mol/L氨水将产物洗脱。得162mg二碳酸阿贝卡星,收率12%,熔点178℃(分解),[α]{D}^24+87°(C=0.77,水)。
用途
对卡那霉素、庆大霉素、丁胺卡那霉素耐药菌有强的抗菌活力。用于敏感菌引起的败血症、肺炎等。
生产方法 3’,4’-二脱氧卡那霉素B和等当量的叔丁氧羰基叠氮化物,在水、吡啶和三乙胺(10:10:1)的混合溶液中,在室温下反应18h。然后用Amberlite CG50(NH4+)柱层析,得6’-N-叔丁氧羰基-3’,4’-二脱氧卡那霉素B,收率49%,熔点136~140℃(分解),[α] {D}^26+112°(C=1.0,水)。同时回收36%未反应的3’,4’-二脱氧卡那霉素B。6’-N-叔丁氧羰基-3’,4’-二脱氧卡那霉素B(1.1g,2.0mmo1)和叔丁氧羰基叠氮化物(320mg,2.2mmo1)在和上述相同的条件下反应,得到1.41g黄色粉末。不用提纯,溶于20ml水和10ml二甲氧基乙烷,用(S)-4-叔丁氧羰基氨基-2-羟基丁酸(N-羟基丁二酰亚胺)酯(696mg,2.2mmo1)在10ml二甲氧基乙烷中的溶液,在室温下酰化20h。和10ml 90%三氟乙酸在室温下反应40min,移去叔丁氧羰基。反应液浓缩至于,用Amberlite CG50(NH4+)柱层析,用水和0.5mol/L氨水洗脱后,再用0.75mol/L氨水将产物洗脱。得162mg二碳酸阿贝卡星,收率12%,熔点178℃(分解),[α]{D}^24+87°(C=0.77,水)。
专业数据库参考
PubChemId 68682
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