2-methoxy-3-(5-methoxypentyl)-7-chlorotriazolo[4,5-c]pyridine | 579486-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: 2-methoxy-3-(5-methoxypentyl)-7-chlorotriazolo[4,5-c]pyridine
• 英文别名: 3-(5-methoxypentyl)-4-methoxy-6-chloro-1,2,3-triazolo[4,5-c]pyridine；6-Chloro-4-methoxy-3-(5-methoxypentyl)triazolo[4,5-c]pyridine
• CAS: 579486-73-0
• 化学式: C₁₂H₁₇ClN₄O₂
• 分子量: 284.746
• InChiKey: MJPMITLLUGZZBN-UHFFFAOYSA-N

物化性质

• 沸点：
  430.1±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  62.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methoxy-3-(5-methoxypentyl)-7-chlorotriazolo[4,5-c]pyridine 、 3,4-二氯苄胺 反应 24.0h， 以62%的产率得到3-(5-methoxypentyl)-7-(3,4-dichlorobenzylamino)triazolo[4,5-c]pyridine-2-one
  参考文献：
  名称：

  7-Alkyl-N2-substituted-3-deazaguanines. Synthesis, DNA polymerase III inhibition and antibacterial activity

  摘要：

  Several 2-anilino- and 2-benzylamino-3-deaza-6-oxopurines [3-deazaguanines] and selected 8-methyl and 8-aza analogs have been synthesized. 7-Substituted N-2-(3-ethyl-4-methylphenyl)-3-deazaguanines were potent and selective inhibitors of Gram+ bacterial DNA polymerase (pol) IIIC, and 7-substituted N-2-(3,4-dichlorobenzyl)-3-deazaguanines were potent inhibitors of both pol IIIC and pol IIIE from Gram+ bacteria, but weakly inhibited pol IIIE from Gram- bacteria. Potent enzyme inhibitors in both classes inhibited the growth of Gram+ bacteria (MICs 2.5-10 mu g/ml), and were inactive against the Gram- organism Escherichia coli. Several derivatives had moderate protective activity in Staphylococcus aureus-infected mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.093
• 作为产物：
  描述：

  3,4-二氨基-2,6-二氯吡啶盐酸盐 在 盐酸 、 四丁基碘化铵 、 potassium carbonate 、 sodium nitrite 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.08h， 生成 2-methoxy-3-(5-methoxypentyl)-7-chlorotriazolo[4,5-c]pyridine 、 2-methoxy-5-(5-methoxypentyl)-7-chlorotriazolo[4,5-c]pyridine
  参考文献：
  名称：

  7-Alkyl-N2-substituted-3-deazaguanines. Synthesis, DNA polymerase III inhibition and antibacterial activity

  摘要：

  Several 2-anilino- and 2-benzylamino-3-deaza-6-oxopurines [3-deazaguanines] and selected 8-methyl and 8-aza analogs have been synthesized. 7-Substituted N-2-(3-ethyl-4-methylphenyl)-3-deazaguanines were potent and selective inhibitors of Gram+ bacterial DNA polymerase (pol) IIIC, and 7-substituted N-2-(3,4-dichlorobenzyl)-3-deazaguanines were potent inhibitors of both pol IIIC and pol IIIE from Gram+ bacteria, but weakly inhibited pol IIIE from Gram- bacteria. Potent enzyme inhibitors in both classes inhibited the growth of Gram+ bacteria (MICs 2.5-10 mu g/ml), and were inactive against the Gram- organism Escherichia coli. Several derivatives had moderate protective activity in Staphylococcus aureus-infected mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.093

文献信息

• Purine and isosteric antibacterial compounds
  申请人：——

  公开号：US20040014773A1

  公开（公告）日：2004-01-22

  The invention features 2,7-disubstituted purines and their isosteres such as the corresponding 3-deazapurines and 3-deaza-8-azapurines. The compounds disclosed herein have potent anti-microbial, e.g., anti-bacterial and anti-mycoplasmal properties. The compounds described herein inhibit DNA polymerase IIIC and DNA polymerase IIIE species; the compounds thus inhibit the growth of bacteria and mycoplasmata. The compounds can be administered to prevent or to treat Gram-positive or Gram-negative bacterial or mycoplasmal infections, e.g., in eukaryotic cell cultures, animals, or humans.

  本发明涉及2,7-二取代嘌呤及其异构体，如相应的3-去氮嘌呤和3-去氮-8-氮杂嘌呤。本文所披露的化合物具有强大的抗微生物，例如抗细菌和抗支原体的特性。本文所描述的化合物抑制DNA聚合酶IIIC和DNA聚合酶IIIE物种；因此，这些化合物抑制了细菌和支原体的生长。这些化合物可用于预防或治疗革兰氏阳性或革兰氏阴性细菌或支原体感染，例如在真核细胞培养物、动物或人类中。
• US6926763B2
  申请人：——

  公开号：US6926763B2

  公开（公告）日：2005-08-09
• 7-Alkyl-N2-substituted-3-deazaguanines. Synthesis, DNA polymerase III inhibition and antibacterial activity
  作者：Wei-chu Xu、George E. Wright、Neal C. Brown、Zheng-yu Long、Cheng-xin Zhi、Sofya Dvoskin、Joseph J. Gambino、Marjorie H. Barnes、Michelle M. Butler

  DOI：10.1016/j.bmcl.2011.05.093

  日期：2011.7

  Several 2-anilino- and 2-benzylamino-3-deaza-6-oxopurines [3-deazaguanines] and selected 8-methyl and 8-aza analogs have been synthesized. 7-Substituted N-2-(3-ethyl-4-methylphenyl)-3-deazaguanines were potent and selective inhibitors of Gram+ bacterial DNA polymerase (pol) IIIC, and 7-substituted N-2-(3,4-dichlorobenzyl)-3-deazaguanines were potent inhibitors of both pol IIIC and pol IIIE from Gram+ bacteria, but weakly inhibited pol IIIE from Gram- bacteria. Potent enzyme inhibitors in both classes inhibited the growth of Gram+ bacteria (MICs 2.5-10 mu g/ml), and were inactive against the Gram- organism Escherichia coli. Several derivatives had moderate protective activity in Staphylococcus aureus-infected mice. (C) 2011 Elsevier Ltd. All rights reserved.