(3-methylfuran-2-yl)methyl acetate | 1397696-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (3-methylfuran-2-yl)methyl acetate
• 英文别名: (3-Methylfuran-2-yl)methyl acetate
• CAS: 1397696-93-3
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: YCIGEINEBLOSDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-methylfuran-2-yl)methyl acetate 在 哌啶 、 氨 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 5-[2-[(6-Chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-5-methyl-4,6-dioxopyrazolo[3,4-d]pyrimidin-3-yl]-4-methylfuran-2-carbonitrile
  参考文献：
  名称：

  Design of inhibitors of Helicobacter pylori glutamate racemase as selective antibacterial agents: Incorporation of imidazoles onto a core pyrazolopyrimidinedione scaffold to improve bioavailabilty

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.07.004
• 作为产物：
  描述：

  3-甲基-2-呋喃甲酸甲酯 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3-methylfuran-2-yl)methyl acetate
  参考文献：
  名称：

  取代对硫醇诱导的氧杂降冰片二烯断裂的影响

  摘要：

  氧杂降冰片二烯 (OND) 与硫醇进行简单的迈克尔加成，然后通过逆狄尔斯-阿尔德 (rDA) 反应进行片段化，这是亲电可切割键之间的独特两步序列。研究了 rDA 反应速率与呋喃结构的函数关系，发现 2 位和 5 位的取代基影响最大，碎裂率与吸电子能力呈负相关。密度泛函理论计算提供了与实验测量的 OND rDA 率的极好相关性。

  DOI：

  10.1021/acs.orglett.1c01164

文献信息

• The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation
  作者：Lucrezia De Pascalis、Mei-Kwan Yau、Dennis Svatunek、Zhuoting Tan、Srinivas Tekkam、K. N. Houk、M. G. Finn

  DOI：10.1021/acs.orglett.1c01164

  日期：2021.5.7

  Oxanorbornadienes (ONDs) undergo facile Michael addition with thiols and then fragment by a retro-Diels–Alder (rDA) reaction, a unique two-step sequence among electrophilic cleavable linkages. The rDA reaction rate was explored as a function of the furan structure, with substituents at the 2- and 5-positions found to be the most influential and the fragmentation rate to be inversely correlated with

  氧杂降冰片二烯 (OND) 与硫醇进行简单的迈克尔加成，然后通过逆狄尔斯-阿尔德 (rDA) 反应进行片段化，这是亲电可切割键之间的独特两步序列。研究了 rDA 反应速率与呋喃结构的函数关系，发现 2 位和 5 位的取代基影响最大，碎裂率与吸电子能力呈负相关。密度泛函理论计算提供了与实验测量的 OND rDA 率的极好相关性。
• 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.