3-ethynyl-3-methoxybenzene-5,6-dihydro-4H-pyrrolo[1,2-c][1,2,3]triazole | 1445792-75-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-ethynyl-3-methoxybenzene-5,6-dihydro-4H-pyrrolo[1,2-c][1,2,3]triazole
• 英文别名: 3-[2-(3-methoxyphenyl)ethynyl]-5,6-dihydro-4H-pyrrolo[1,2-c]triazole
• CAS: 1445792-75-5
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: KSESGTJXSAPNER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-(3-methoxyphenyl)hepta-4,6-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78%的产率得到3-ethynyl-3-methoxybenzene-5,6-dihydro-4H-pyrrolo[1,2-c][1,2,3]triazole
  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

• 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.