6-chloro-2-(furan-2-yl)-N-(4-methoxybenzyl)-3-nitropyridin-4-amine | 1313714-49-6

• 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: 6-chloro-2-(furan-2-yl)-N-(4-methoxybenzyl)-3-nitropyridin-4-amine
• 英文别名: 6-chloro-2-(furan-2-yl)-N-[(4-methoxyphenyl)methyl]-3-nitropyridin-4-amine
• CAS: 1313714-49-6
• 化学式: C₁₇H₁₄ClN₃O₄
• 分子量: 359.769
• InChiKey: GUYQDDCSTPWZKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-chloro-2-(furan-2-yl)-N-(4-methoxybenzyl)-3-nitropyridin-4-amine 在 sodium dithionite 、 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以93%的产率得到6-chloro-2-(furan-2-yl)-N4-(4-methoxybenzyl)pyridine-3,4-diamine
  参考文献：
  名称：

  Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: Imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles

  摘要：

  6,9-Disubstituted purines and 7-deazapurines are known to be powerful inhibitors of Mycobacterium tuberculosis (Mtb) in vitro. Analogs modified in the six-membered ring (imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles) were synthesized and evaluated as Mtb inhibitors. The targets were prepared by functionalization on the bicyclic heterocycle or from simple pyridines. The results reported herein, indicate that the purine N-1, but not N-3, is important for binding to the unknown target. The 3-deazapurines appears to be slightly more active compared to the parent purines and slightly less active than their 7-deazapurine isomers. Removal of both the purine N-3 and N-7 did not result in further enhanced antimycobacterial activity but the toxicity towards mammalian cells was increased. Both 3-deaza and 3,7-dideazapurines exhibited a modest activity against of the Mtb isolate in the state of non-replicating persistence. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.023
• 作为产物：
  描述：

  4-氨基-2,6-二氯-3-硝基吡啶嘧啶 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 6-chloro-2-(furan-2-yl)-N-(4-methoxybenzyl)-3-nitropyridin-4-amine
  参考文献：
  名称：

  Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: Imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles

  摘要：

  6,9-Disubstituted purines and 7-deazapurines are known to be powerful inhibitors of Mycobacterium tuberculosis (Mtb) in vitro. Analogs modified in the six-membered ring (imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles) were synthesized and evaluated as Mtb inhibitors. The targets were prepared by functionalization on the bicyclic heterocycle or from simple pyridines. The results reported herein, indicate that the purine N-1, but not N-3, is important for binding to the unknown target. The 3-deazapurines appears to be slightly more active compared to the parent purines and slightly less active than their 7-deazapurine isomers. Removal of both the purine N-3 and N-7 did not result in further enhanced antimycobacterial activity but the toxicity towards mammalian cells was increased. Both 3-deaza and 3,7-dideazapurines exhibited a modest activity against of the Mtb isolate in the state of non-replicating persistence. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.023