[4-(2-furyl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl](4-methoxyphenyl)methanone | 1255939-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [4-(2-furyl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl](4-methoxyphenyl)methanone
• 英文别名: [4-(2-Furyl)-5-methyl-pyrrolo[3,2-d]pyrimidin-7-yl]-(4-methoxyphenyl)methanone；[4-(furan-2-yl)-5-methylpyrrolo[3,2-d]pyrimidin-7-yl]-(4-methoxyphenyl)methanone
• CAS: 1255939-64-0
• 化学式: C₁₉H₁₅N₃O₃
• 分子量: 333.346
• InChiKey: JVTDKRABNDWGFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [4-(2-furyl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl](4-methoxyphenyl)methanone 在 一水合肼 、 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 18.0h， 以71%的产率得到4-(2-furyl)-7-(4-methoxybenzyl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine
  参考文献：
  名称：

  Synthesis of non-purine analogs of 6-aryl-9-benzylpurines, and their antimycobacterial activities. Compounds modified in the imidazole ring

  摘要：

  Purine analogs modified in the five-membered ring have been synthesized and examined for antibacterial activity against Mycobacterium tuberculosis H(37)Rv in vitro employing the microplate alamar blue assay (MABA). The 9-deaza analogs were only found to be weak inhibitors, but the 8-aza-, 7-deaza- and 8-aza-7-deazapurine analogs studied displayed excellent antimycobacterial activities, some even substantially better than the parent purine. In the 7-deazapurine series, MIC values between 0.08 and 0.35 mu M, values comparable or better than the reference drugs used in the study (MIC rifampicin 0.09 mu M, MIC isoniazid 0.28 mu M and MIC PA-824 0.44 mu M). The five most active compounds were also examined against a panel of drug-resistant Mtb strain, and they all retained their activity. The compounds examined were significantly less active against M. tuberculosis in a state of non-replicating persistence (NRP). MIC in the low-oxygen-recovery assay (LORA) >= 60 mu M. The 7-deazapurines were somewhat more toxic towards mammalian cells, but still the selectivity indexes were excellent. The non-purine analogs exhibit a selective antimycobacterial activity. They were essentially inactive against Staphylococcus aureus and Escherichia coli. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.016
• 作为产物：
  描述：

  (4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)(4-methoxyphenyl)methanone 、 2-(三丁基锡烷基)呋喃 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以72%的产率得到[4-(2-furyl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl](4-methoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis of non-purine analogs of 6-aryl-9-benzylpurines, and their antimycobacterial activities. Compounds modified in the imidazole ring

  摘要：

  Purine analogs modified in the five-membered ring have been synthesized and examined for antibacterial activity against Mycobacterium tuberculosis H(37)Rv in vitro employing the microplate alamar blue assay (MABA). The 9-deaza analogs were only found to be weak inhibitors, but the 8-aza-, 7-deaza- and 8-aza-7-deazapurine analogs studied displayed excellent antimycobacterial activities, some even substantially better than the parent purine. In the 7-deazapurine series, MIC values between 0.08 and 0.35 mu M, values comparable or better than the reference drugs used in the study (MIC rifampicin 0.09 mu M, MIC isoniazid 0.28 mu M and MIC PA-824 0.44 mu M). The five most active compounds were also examined against a panel of drug-resistant Mtb strain, and they all retained their activity. The compounds examined were significantly less active against M. tuberculosis in a state of non-replicating persistence (NRP). MIC in the low-oxygen-recovery assay (LORA) >= 60 mu M. The 7-deazapurines were somewhat more toxic towards mammalian cells, but still the selectivity indexes were excellent. The non-purine analogs exhibit a selective antimycobacterial activity. They were essentially inactive against Staphylococcus aureus and Escherichia coli. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.016