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tert-butyl ((3S,6R)-6-(((1-phenyl-1H-tetrazol-5-yl)sulfonyl)-methyl)tetrahydro-2H-pyran-3-yl)carbamate | 881657-99-4

中文名称
——
中文别名
——
英文名称
tert-butyl ((3S,6R)-6-(((1-phenyl-1H-tetrazol-5-yl)sulfonyl)-methyl)tetrahydro-2H-pyran-3-yl)carbamate
英文别名
tert-butyl N-[(3S,6R)-6-[(1-phenyltetrazol-5-yl)sulfonylmethyl]oxan-3-yl]carbamate
tert-butyl ((3S,6R)-6-(((1-phenyl-1H-tetrazol-5-yl)sulfonyl)-methyl)tetrahydro-2H-pyran-3-yl)carbamate化学式
CAS
881657-99-4
化学式
C18H25N5O5S
mdl
——
分子量
423.493
InChiKey
GRCYJTGPLQQLOX-DZGCQCFKSA-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

计算性质

  • 辛醇/水分配系数(LogP):
    2
  • 重原子数:
    29
  • 可旋转键数:
    7
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.56
  • 拓扑面积:
    134
  • 氢给体数:
    1
  • 氢受体数:
    8

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Design, Synthesis, and Characterization of Novel Tetrahydropyran-Based Bacterial Topoisomerase Inhibitors with Potent Anti-Gram-Positive Activity
    摘要:
    There is an urgent need for new antibacterial drugs that are effective against infections caused by multidrug-resistant pathogens. Novel nonfluoroquinolone inhibitors of bacterial type II topoisomerases (DNA gyrase and topoisomerase IV) have the potential to become such drugs because they display potent antibacterial activity and exhibit no target-mediated cross-resistance with fluoroquinolones. Bacterial topoisomerase inhibitors that are built on a tetrahydropyran ring linked to a bicyclic aromatic moiety through a syn-diol linker show potent anti-Gram-positive activity, covering isolates with clinically relevant resistance phenotypes. For instance, analog 49c was found to be a dual DNA gyrase topoisomerase IV inhibitor, with broad antibacterial activity and low propensity for spontaneous resistance development, but suffered from high hERG K channel block. On the other hand, analog 49e displayed lower hERG K channel block while retaining potent in vitro antibacterial activity and acceptable frequency for resistance development. Furthermore, analog 49e showed moderate clearance in rat and promising in vivo efficacy against Staphylococcus aureus in a murine infection model.
    DOI:
    10.1021/jm400963y
  • 作为产物:
    描述:
    (S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester4-二甲氨基吡啶锂硼氢 、 hexaammonium heptamolybdate tetrahydrate 、 camphor-10-sulfonic acid 、 双氧水三乙胺间氯过氧苯甲酸 、 sodium iodide 、 potassium hydroxide 作用下, 以 四氢呋喃 、 aq. phosphate buffer 、 乙醇二氯甲烷1,2-二氯乙烷丙酮 为溶剂, 反应 39.0h, 生成 tert-butyl ((3S,6R)-6-(((1-phenyl-1H-tetrazol-5-yl)sulfonyl)-methyl)tetrahydro-2H-pyran-3-yl)carbamate
    参考文献:
    名称:
    Design, Synthesis, and Characterization of Novel Tetrahydropyran-Based Bacterial Topoisomerase Inhibitors with Potent Anti-Gram-Positive Activity
    摘要:
    There is an urgent need for new antibacterial drugs that are effective against infections caused by multidrug-resistant pathogens. Novel nonfluoroquinolone inhibitors of bacterial type II topoisomerases (DNA gyrase and topoisomerase IV) have the potential to become such drugs because they display potent antibacterial activity and exhibit no target-mediated cross-resistance with fluoroquinolones. Bacterial topoisomerase inhibitors that are built on a tetrahydropyran ring linked to a bicyclic aromatic moiety through a syn-diol linker show potent anti-Gram-positive activity, covering isolates with clinically relevant resistance phenotypes. For instance, analog 49c was found to be a dual DNA gyrase topoisomerase IV inhibitor, with broad antibacterial activity and low propensity for spontaneous resistance development, but suffered from high hERG K channel block. On the other hand, analog 49e displayed lower hERG K channel block while retaining potent in vitro antibacterial activity and acceptable frequency for resistance development. Furthermore, analog 49e showed moderate clearance in rat and promising in vivo efficacy against Staphylococcus aureus in a murine infection model.
    DOI:
    10.1021/jm400963y
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文献信息

  • NEW BICYCLIC ANTIBIOTICS
    申请人:Actelion Pharmaceuticals Ltd.
    公开号:EP1799676A2
    公开(公告)日:2007-06-27
  • [EN] NEW BICYCLIC ANTIBIOTICS<br/>[FR] NOUVEAUX ANTIBIOTIQUES BICYCLIQUES
    申请人:ACTELION PERCUREX AG
    公开号:WO2006032466A2
    公开(公告)日:2006-03-30
    The invention relates to novel antibiotics of formula (I) wherein R1 represents alkyl, alkoxy, haloalkoxy, halogen or cyano; one or two of U, V, W and X represent(s) N, the remaining represent CH, or, in case of U, V and/or W, may also represent CRa and, in the case of X, may also represent CRb; Ra represents halogen; Rb represents halogen or alkoxy; M is a linking chain containing a non-aromatic cyclic or heterocyclic group, and D represents alkyl, aryl or heteroaryl.
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