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4-nitrobenzyl 3-hydroxy-2,6-dimethylbenzoate | 676346-98-8

中文名称
——
中文别名
——
英文名称
4-nitrobenzyl 3-hydroxy-2,6-dimethylbenzoate
英文别名
(4-nitrophenyl)methyl 3-hydroxy-2,6-dimethylbenzoate
4-nitrobenzyl 3-hydroxy-2,6-dimethylbenzoate化学式
CAS
676346-98-8
化学式
C16H15NO5
mdl
——
分子量
301.299
InChiKey
YHDZIHVGZVULJK-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    491.0±40.0 °C(Predicted)
  • 密度:
    1.305±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.27
  • 重原子数:
    22.0
  • 可旋转键数:
    4.0
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.19
  • 拓扑面积:
    89.67
  • 氢给体数:
    1.0
  • 氢受体数:
    5.0

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    4-nitrobenzyl 3-hydroxy-2,6-dimethylbenzoate 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS)氢气三乙胺 作用下, 以 四氯化碳乙酸乙酯N,N-二甲基甲酰胺 为溶剂, 反应 26.67h, 生成 6-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methyl-benzoic acid
    参考文献:
    名称:
    New Antibacterial Agents Derived from the DNA Gyrase Inhibitor Cyclothialidine
    摘要:
    Cyclothialidine (1, Ro 09-1437) is a potent DNA gyrase inhibitor that was isolated from Streptomyces filipinensis NR0484 and is a member of a new family of natural products. It acts by competitively inhibiting the ATPase activity exerted by the B subunit of DNA gyrase but barely exhibits any growth inhibitory activity against intact bacterial cells, presumably due to insufficient permeation of the cytoplasmic membrane. To explore the antibacterial potential of 1, we developed a flexible synthetic route allowing for the systematic modification of its structure. From a first set of analogues, structure-activity relationships (SAR) were established for different substitution patterns, and the 14-hydroxylated, bicyclic core (X) of 1 seemed to be the structural prerequisite for DNA gyrase inhibitory activity. The variation of the lactone ring size, however, revealed that activity can be found among 11- to 16-membered lactones, and even seco-analogues were shown to maintain some enzyme inhibitory properties, thereby reducing the minimal structural requirements to a rather simple, hydroxylated benzyl sulfide (XI). On the basis of these "minimal structures" a modification program afforded a number of inhibitors that showed in vitro activity against Gram-positive bacteria. The best activities were displayed by 14-membered lactones, and representatives of this subclass exhibit excellent and broad in vitro antibacterial activity against Gram-positive pathogens, including Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, and overcome resistance against clinically used drugs. By improving the pharmacokinetic properties of the most active compounds (94, 97), in particular by lowering their lipophilic properties, we were able to identify congeners of cyclothialidine (1) that showed efficacy in vivo.
    DOI:
    10.1021/jm0310232
  • 作为产物:
    描述:
    3-hydroxy-2,6-dimethylbenzoic acid对硝基溴化苄四甲基胍 作用下, 以 N,N-二甲基甲酰胺 为溶剂, 反应 72.5h, 以76%的产率得到4-nitrobenzyl 3-hydroxy-2,6-dimethylbenzoate
    参考文献:
    名称:
    New Antibacterial Agents Derived from the DNA Gyrase Inhibitor Cyclothialidine
    摘要:
    Cyclothialidine (1, Ro 09-1437) is a potent DNA gyrase inhibitor that was isolated from Streptomyces filipinensis NR0484 and is a member of a new family of natural products. It acts by competitively inhibiting the ATPase activity exerted by the B subunit of DNA gyrase but barely exhibits any growth inhibitory activity against intact bacterial cells, presumably due to insufficient permeation of the cytoplasmic membrane. To explore the antibacterial potential of 1, we developed a flexible synthetic route allowing for the systematic modification of its structure. From a first set of analogues, structure-activity relationships (SAR) were established for different substitution patterns, and the 14-hydroxylated, bicyclic core (X) of 1 seemed to be the structural prerequisite for DNA gyrase inhibitory activity. The variation of the lactone ring size, however, revealed that activity can be found among 11- to 16-membered lactones, and even seco-analogues were shown to maintain some enzyme inhibitory properties, thereby reducing the minimal structural requirements to a rather simple, hydroxylated benzyl sulfide (XI). On the basis of these "minimal structures" a modification program afforded a number of inhibitors that showed in vitro activity against Gram-positive bacteria. The best activities were displayed by 14-membered lactones, and representatives of this subclass exhibit excellent and broad in vitro antibacterial activity against Gram-positive pathogens, including Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, and overcome resistance against clinically used drugs. By improving the pharmacokinetic properties of the most active compounds (94, 97), in particular by lowering their lipophilic properties, we were able to identify congeners of cyclothialidine (1) that showed efficacy in vivo.
    DOI:
    10.1021/jm0310232
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同类化合物

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