ethyl 5-(4-fluorophenyl)-2H-tetrazol-2-ylacetate | 50907-29-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 5-(4-fluorophenyl)-2H-tetrazol-2-ylacetate
• 英文别名: [5-(4-fluoro-phenyl)-tetrazol-2-yl]-acetic acid ethyl ester；Ethyl 2-[5-(4-fluorophenyl)tetrazol-2-yl]acetate
• CAS: 50907-29-4
• 化学式: C₁₁H₁₁FN₄O₂
• 分子量: 250.232
• InChiKey: SAXVUUSAPAKIGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-fluorophenyl)-2H-tetrazol-2-ylacetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以95%的产率得到5-(4-fluorophenyl)-2H-tetrazol-2-ylacethydrazide
  参考文献：
  名称：

  合成一些较新的5-（5-芳基-2 H-四唑-2-基甲基）-4-取代的-s-三唑-3-硫醇作为抗炎药

  摘要：

  几种1-（5-芳基-2 H-四唑-2-基乙酰基）-4-取代的硫代氨基脲和5-（5-芳基-2 H-四唑-2-基甲基）-4-取代的-s-三唑-合成了3-硫醇作为可能的抗炎药。这些化合物的特征在于其元素，红外和核磁共振分析。

  DOI：

  10.1002/jhet.5570170709
• 作为产物：
  描述：

  对氟苯腈 在 sodium azide 、 sodium ethanolate 、 三乙胺盐酸盐 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 ethyl 5-(4-fluorophenyl)-2H-tetrazol-2-ylacetate
  参考文献：
  名称：

  Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators

  摘要：

  The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.

  DOI：

  10.1016/j.bmcl.2019.01.027

文献信息

• Synthesis and Structure–Activity Studies of β-Barrel Assembly Machine Complex Inhibitor MRL-494
  作者：Nicola Wade、Charlotte M. J. Wesseling、Paolo Innocenti、Cornelis J. Slingerland、Gregory M. Koningstein、Joen Luirink、Nathaniel I. Martin

  DOI：10.1021/acsinfecdis.2c00459

  日期：2022.11.11

  β-barrel assembly machine (BAM) complex has become an increasingly interesting target. The recently reported BAM complex inhibitor, MRL-494, was discovered via a screening campaign for molecules that target the outer membrane. Notably, MRL-494 was reported to be an unintended byproduct generated during the synthesis of an unrelated compound, and as such no synthesis of the compound was disclosed. We

  在寻找具有抗革兰氏阴性病原体活性的新抗生素时，外膜 β 桶组装机 (BAM) 复合体已成为一个越来越有趣的目标。最近报道的 BAM 复合物抑制剂 MRL-494 是通过针对外膜分子的筛选活动发现的。值得注意的是，据报道 MRL-494 是一种无关化合物合成过程中产生的意外副产物，因此没有公开该化合物的合成。我们在这里提出了一种方便可靠的合成 MRL-494 的途径，该途径可以很好地扩展。合成的 MRL-494 的抗菌活性与文献中报道的相匹配。此外，发现 MRL-494 与利福平对革兰氏阴性菌（包括大肠杆菌）表现出强大的协同作用、肺炎克雷伯菌、鲍曼不动杆菌和铜绿假单胞菌。还发现 MRL-494 会导致外膜破坏和 Rcs 应激反应途径的诱导。此外，我们进行了一项重点结构-活性研究，专门旨在阐明 MRL-494 结构中包含的两个胍部分所起的作用。
• KOTHARI P. J.; SINGH S. P.; PARMAR S. S.; STENBERG V. I., J. HETEROCYCL. CHEM., 1980, 17, NO 7, 1393-1398
  作者：KOTHARI P. J.、 SINGH S. P.、 PARMAR S. S.、 STENBERG V. I.

  DOI：——

  日期：——
• Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators
  作者：Swagat Sharma、Krystian A. Kozek、Kristopher K. Abney、Sushil Kumar、Nagsen Gautam、Yazen Alnouti、C. David Weaver、Corey R. Hopkins

  DOI：10.1016/j.bmcl.2019.01.027

  日期：2019.3

  The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.
• Synthesis of some newer 5-(5-aryl-2<i>H</i>-tetrazol-2-ylmethyl)-4-substituted-<i>s</i>-triazole-3-thiols as possible antiinflammatory agents
  作者：Paresh J. Kothari、Shiva P. Singh、Surendra S. Parmar、Virgil I. Stenberg

  DOI：10.1002/jhet.5570170709

  日期：1980.11

  Several 1-(5-aryl-2H-tetrazol-2-ylacetyl)-4-substituted thiosemicarbazides and 5-(5-aryl-2H-tetrazol-2-yl-methyl)-4-substituted-s-triazole-3-thiols were synthesized as possible antiinflammatory agents. These compounds were characterized by their elemental, infrared and nuclear magnetic resonance analysis.

  几种1-（5-芳基-2 H-四唑-2-基乙酰基）-4-取代的硫代氨基脲和5-（5-芳基-2 H-四唑-2-基甲基）-4-取代的-s-三唑-合成了3-硫醇作为可能的抗炎药。这些化合物的特征在于其元素，红外和核磁共振分析。