3-phenyl-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine | 63412-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-phenyl-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine
• 英文别名: 3-Phenyl-4,5,6,7-tetrahydrotriazolo[1,5-a]pyridine
• CAS: 63412-04-4
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: WUJQJXODMZXHED-UHFFFAOYSA-N

物化性质

• 熔点：
  97 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  401.3±53.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-苯基己-5-炔-1-醇 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 0.33h， 以83%的产率得到3-phenyl-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

• Triazolopyridines. Part 30. Hydrogen transfer reactions; pyridylcarbene formation
  作者：Belén Abarca、Rosa Adam、Shamim Alom、Rafael Ballesteros、Sonia López-Molina

  DOI：10.3998/ark.5550190.p008.227

  日期：——

  hydrogenation reaction of (1,2,3)triaz olo(1,5-a)pyridines with Pd/C/Zn or Pd(OH) 2/C/Zn in water, ethanol or water/ethanol mixture ha s been explored. 4,5,6,7-Tetrahydro- triazolopyridines were obtained in good to medium yields. In addition, under the same conditions 2-substituted pyridines were also formed as a resul t of intermediate pyridylcarbene formation, by triazole ring opening and loss of nitrogen

  (1,2,3)triaz olo(1,5-a)吡啶与Pd/C/Zn或Pd(OH) 2/C/Zn在水、乙醇或水/乙醇混合物中的转移加氢反应已有探索。4,5,6,7-四氢-三唑并吡啶以良好至中等产率获得。此外，在相同条件下，由于三唑开环和氮损失，中间体吡啶卡宾形成的结果也形成了 2-取代的吡啶。
• Discovery, Synthetic Methodology, and Biological Evaluation for Antiphotoaging Activity of Bicyclic[1,2,3]triazoles: In Vitro and in Vivo Studies
  作者：Hsin-Yu Hsieh、Wen-Chun Lee、Gopal Chandru Senadi、Wan-Ping Hu、Jium-Jia Liang、Tong-Rong Tsai、Yu-Wei Chou、Kung-Kai Kuo、Chung-Yu Chen、Jeh-Jeng Wang

  DOI：10.1021/jm400394s

  日期：2013.7.11

  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.