tert-butyl 5-O-[5-tert-butoxycarbonylamino-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-6-deoxy-2,3-O-isopropylidene-6-(4-octylbenzoylamino)-1-(uracil-1-yl)-β-D-glycero-L-talo-heptofuranuronate | 1223563-61-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 5-O-[5-tert-butoxycarbonylamino-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-6-deoxy-2,3-O-isopropylidene-6-(4-octylbenzoylamino)-1-(uracil-1-yl)-β-D-glycero-L-talo-heptofuranuronate
• 英文别名: tert-butyl (2S,3S)-3-[[(3aR,4S,6R,6aR)-2,2-diethyl-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxy]-3-[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-[(4-octylbenzoyl)amino]propanoate
• CAS: 1223563-61-8
• 化学式: C₄₈H₇₂N₄O₁₄
• 分子量: 929.118
• InChiKey: PXLWUVCFGSZBTJ-GKQQAGEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  208
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-O-[5-tert-butoxycarbonylamino-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-6-deoxy-2,3-O-isopropylidene-6-(4-octylbenzoylamino)-1-(uracil-1-yl)-β-D-glycero-L-talo-heptofuranuronate 、 三氟乙酸 以 水 为溶剂， 反应 6.0h， 以95%的产率得到5-O-(5-amino-5-deoxy-β-D-ribofuranosyl)-6-deoxy-1-6-(4-octylbenzolyamino)-1-(uracil-1-yl)-β-D-glycero-L-talo-heptofuranuronic acid trifluoroacetate salt
  参考文献：
  名称：

  Function-Oriented Synthesis of Simplified Caprazamycins: Discovery of Oxazolidine-Containing Uridine Derivatives as Antibacterial Agents against Drug-Resistant Bacteria

  摘要：

  The rational simplification of the caprazamycin (CPZ) class of nucleoside natural products was carried out to address their molecular complexity. First, analogues 6-8, where the diazepanone ring of the CPZ was removed and a lipophilic side chain was attached to either the C-7' or N(6') atom, were used to investigate the conformation activity relationship. On the basis of this relationship, we designed the oxazolidine-containing uridine derivatives 18-21 by restricting the conformation of 6-8. As a result, the 'Bu ester derivatives 20 were found to be the most active against a range of bacterial strains containing VRE with a potency similar to that of the parent CPZs. This study provides a novel strategy for the development of a new type of antibacterial agent effective against drug-resistant bacteria.

  DOI：

  10.1021/jm100243n
• 作为产物：
  描述：

  tert-butyl (2S,3S)-3-[[(3aR,4S,6R,6aR)-2,2-diethyl-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxy]-3-[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-aminopropanoate 、 4-正辛基苯甲酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以76 mg的产率得到tert-butyl 5-O-[5-tert-butoxycarbonylamino-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-6-deoxy-2,3-O-isopropylidene-6-(4-octylbenzoylamino)-1-(uracil-1-yl)-β-D-glycero-L-talo-heptofuranuronate
  参考文献：
  名称：

  Function-Oriented Synthesis of Simplified Caprazamycins: Discovery of Oxazolidine-Containing Uridine Derivatives as Antibacterial Agents against Drug-Resistant Bacteria

  摘要：

  The rational simplification of the caprazamycin (CPZ) class of nucleoside natural products was carried out to address their molecular complexity. First, analogues 6-8, where the diazepanone ring of the CPZ was removed and a lipophilic side chain was attached to either the C-7' or N(6') atom, were used to investigate the conformation activity relationship. On the basis of this relationship, we designed the oxazolidine-containing uridine derivatives 18-21 by restricting the conformation of 6-8. As a result, the 'Bu ester derivatives 20 were found to be the most active against a range of bacterial strains containing VRE with a potency similar to that of the parent CPZs. This study provides a novel strategy for the development of a new type of antibacterial agent effective against drug-resistant bacteria.

  DOI：

  10.1021/jm100243n

文献信息

• Function-Oriented Synthesis of Simplified Caprazamycins: Discovery of Oxazolidine-Containing Uridine Derivatives as Antibacterial Agents against Drug-Resistant Bacteria
  作者：Kensuke Ii、Satoshi Ichikawa、Bayan Al-Dabbagh、Ahmed Bouhss、Akira Matsuda

  DOI：10.1021/jm100243n

  日期：2010.5.13

  The rational simplification of the caprazamycin (CPZ) class of nucleoside natural products was carried out to address their molecular complexity. First, analogues 6-8, where the diazepanone ring of the CPZ was removed and a lipophilic side chain was attached to either the C-7' or N(6') atom, were used to investigate the conformation activity relationship. On the basis of this relationship, we designed the oxazolidine-containing uridine derivatives 18-21 by restricting the conformation of 6-8. As a result, the 'Bu ester derivatives 20 were found to be the most active against a range of bacterial strains containing VRE with a potency similar to that of the parent CPZs. This study provides a novel strategy for the development of a new type of antibacterial agent effective against drug-resistant bacteria.