4-乙酰基-1-甲基-1H-吡咯-2-甲醛 | 75866-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙酰基-1-甲基-1H-吡咯-2-甲醛
• 英文名称: 4-acetyl-2-formyl-1-methylpyrrole
• 英文别名: 1-methyl-4-acetylpyrrole-2-carboxaldehyde；4-Acetyl-1-methyl-1H-pyrrole-2-carbaldehyde；4-acetyl-1-methylpyrrole-2-carbaldehyde
• CAS: 75866-91-0
• 化学式: C₈H₉NO₂
• mdl: MFCD02179578
• 分子量: 151.165
• InChiKey: OWBXRSMVPDNIEH-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  294.6±25.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-乙酰基-1-甲基-1H-吡咯-2-甲醛 在 palladium on activated charcoal 作用下， 以73%的产率得到3-乙酰基-1-甲基吡咯
  参考文献：
  名称：

  Anderson, Hugh J.; Loader, Charles E.; Foster, Aidan, Canadian Journal of Chemistry, 1980, vol. 58, p. 2527 - 2530

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰氯 、 N-甲基-2-吡咯甲醛 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到4-乙酰基-1-甲基-1H-吡咯-2-甲醛
  参考文献：
  名称：

  Anderson, Hugh J.; Loader, Charles E.; Foster, Aidan, Canadian Journal of Chemistry, 1980, vol. 58, p. 2527 - 2530

  摘要：

  DOI：

文献信息

• [EN] NEW PYRAZOLO[3,4-D]PYRIMIDINES INHIBITING H. PYLORI INFECTIONS<br/>[FR] PYRAZOLO[3,4-D]PYRIMIDINES INHIBANT LES INFECTIONS PAR H. PYLORI
  申请人：ASTRAZENECA AB

  公开号：WO2003002567A1

  公开（公告）日：2003-01-09

  Compounds having the general formula , and pharmaceutical compositions containing them, and their use in the treatment or prophylaxis of H. pylori infection.

  具有一般式的化合物，以及含有它们的制药组合物，以及它们在治疗或预防H. pylori感染中的用途。
• Pyrazolo[3,4-d]pyrimidines inhibiting h. pylori infections
  申请人：——

  公开号：US20040254183A1

  公开（公告）日：2004-12-16

  Compounds having the general formula 1 and pharmaceutical compositions containing them, and their use in the treatment or prophylaxis of H. pylori infection.

  具有通式1的化合物以及含有它们的药物组合物，以及它们在治疗或预防H. pylori感染中的应用。
• Pyrazolo[3,4-d]pyrimidines inhibiting H. pylori infections
  申请人：AstraZeneca AB

  公开号：US07285558B2

  公开（公告）日：2007-10-23

  Compounds having the general formula and pharmaceutical compositions containing them, and their use in the treatment or prophylaxis of H. pylori infection.

  具有一般式的化合物及含有它们的制药组合物，以及它们在治疗或预防幽门螺杆菌感染方面的用途。
• Design of inhibitors of Helicobacter pylori glutamate racemase as selective antibacterial agents: Incorporation of imidazoles onto a core pyrazolopyrimidinedione scaffold to improve bioavailabilty
  作者：Gregory S. Basarab、Pamela Hill、Charles J. Eyermann、Madhu Gowravaram、Helena Käck、Ekundayo Osimoni

  DOI：10.1016/j.bmcl.2012.07.004

  日期：2012.9

  Structure-activity relationships are presented around a series of pyrazolopyrimidinediones that inhibit the growth of Helicobacter pylori by targeting glutamate racemase, an enzyme that provides d-glutamate for the construction of N-acetylglucosamine-N-acetylmuramic acid peptidoglycan subunits assimilated into the bacterial cell wall. Substituents on the inhibitor scaffold were varied to optimize target potency, antibacterial activity and in vivo pharmacokinetic stability. By incorporating an imidazole ring at the 7-position of scaffold, high target potency was achieved due to a hydrogen bonding network that occurs between the 3-position nitrogen atom, a bridging water molecule and the side chains Ser152 and Trp244 of the enzyme. The lipophilicity of the scaffold series proved important for expression of antibacterial activity. Clearances in vitro and in vivo were monitored to identify compounds with improved plasma stability. The basicity of the imidazole may contribute to increased aqueous solubility at lower pH allowing for improved oral bioavailability.
• Gonsalez-Rosende, Eugenia; Jones, R. Alan; Sepulveda-Arques, Jose, Synthetic Communications, 1988, vol. 18, # 14, p. 1669 - 1678
  作者：Gonsalez-Rosende, Eugenia、Jones, R. Alan、Sepulveda-Arques, Jose、Zaballos-Garcia, Elena

  DOI：——

  日期：——