3-ethynyl-2-fluorobenzene-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine | 1445792-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: 3-ethynyl-2-fluorobenzene-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine
• 英文别名: 3-[2-(2-Fluorophenyl)ethynyl]-4,5,6,7-tetrahydrotriazolo[1,5-a]pyridine；3-[2-(2-fluorophenyl)ethynyl]-4,5,6,7-tetrahydrotriazolo[1,5-a]pyridine
• CAS: 1445792-91-5
• 化学式: C₁₄H₁₂FN₃
• 分子量: 241.268
• InChiKey: ONZQMBXEUCXUMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-(2-fluorophenyl)octa-5,7-diyn-1-ol 在 叠氮磷酸二苯酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 150.0 ℃ 、101.33 kPa 条件下， 反应 0.17h， 以77%的产率得到3-ethynyl-2-fluorobenzene-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine
  参考文献：
  名称：

  Discovery, Synthetic Methodology, and Biological Evaluation for Antiphotoaging Activity of Bicyclic[1,2,3]triazoles: In Vitro and in Vivo Studies

  摘要：

  Novel bicyclic[1,2,3]triazoles (4, 7, 11, 15) have been synthesized using a one-pot metal free strategy with high structural diversity as photoprotective agents, and their effect on UVA-induced senescence in human dermal fibroblast cells (FB) and the associated mechanism are delineated. lid plus UVA can induce a decrease in reactive oxygen species (ROS) production and senescence-associated beta-galactosiclase (SA-beta-gal) activity but an increase in adenosine triphosphate (ATP) synthesis and mitochondrial membrane potential (Delta psi(mt)). The mRNA levels of six senescence-associated genes, matrix metalloproteinase-1 (MMP-1), was decreased, while elastin, procollagen I type I, fibronectin, COL1 alpha 1, and tissue inhibitor of metalloproteinase-1 (TIMP-1) were increased. lid plus UVA also decreased MMP-1 and increased TIMP-1 protein levels. Additionally, the thickness of the minim dorsal skin and epidermis, by UVA, was decreased by topical lid treatment. Our results indicate that bicyclic[1,2,3]triazoles protect UVA-induced senescence-like characteristics in FB cells, which may provide potential prevention against photoaging.

  DOI：

  10.1021/jm400394s

文献信息

• Ring-Opening Coupling of Cyclopropanol with 1,2,3-Triazole for the Synthesis of Fused Triazoles
  作者：Yi Wu、Hu Zhang、Qi Wang、Peng Tang、Dan Jiang、Jiahong Mo、Hanyue Qiu、Ling He、Min Zhang

  DOI：10.1021/acs.orglett.4c00702

  日期：2024.5.17

  A radical ring-opening arylation of cyclopropanol with 1,2,3-triazole has been achieved. This synthetic protocol provides straightforward access to a wide range of structurally diverse and chiral 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridines with high efficiency from readily available chiral cyclopropanols.

  已经实现了环丙醇与1,2,3-三唑的自由基开环芳基化。该合成方案可以直接从容易获得的手性环丙醇中高效地获得各种结构多样的手性 4,5,6,7-四氢[1,2,3]三唑并[1,5- a ]吡啶。