1-(2-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole | 860653-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole
• CAS: 860653-74-3
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: HCBJKOYOUQGEHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.94
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以56%的产率得到1-(2-hydroxybenzyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  1,4- and 2,4-substituted-1,2,3-triazoles as potential potassium channel activators. VII

  摘要：

  New 1,4- and 2,4-substituted 1,2,3-triazole derivatives were synthesized and tested as potential BK(Ca) channel openers, as a part of a research program, which hypothesizes a pharmacophoric structure containing the 1,2,3-triazole ring. The structure-activity relationships were studied introducing some structural changes concerning molecular geometry and the presence of a hydrogen bond donor as a primary amino group and a phenolic or alcoholic hydroxy function. The compounds were prepared by nucleophilic substitution on the 1,2,3-triazole ring and by 1,3-dipolar cycloaddition of azides to selected alkynes and to phenylacetone. The new compounds tested on rat aortic rings did not exhibit any significant vasorelaxing activity.

  DOI：

  10.1016/j.farmac.2005.03.004
• 作为产物：
  描述：

  苯乙炔 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium azide 、 potassium carbonate 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 286.0h， 生成 1-(2-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  1,4- and 2,4-substituted-1,2,3-triazoles as potential potassium channel activators. VII

  摘要：

  New 1,4- and 2,4-substituted 1,2,3-triazole derivatives were synthesized and tested as potential BK(Ca) channel openers, as a part of a research program, which hypothesizes a pharmacophoric structure containing the 1,2,3-triazole ring. The structure-activity relationships were studied introducing some structural changes concerning molecular geometry and the presence of a hydrogen bond donor as a primary amino group and a phenolic or alcoholic hydroxy function. The compounds were prepared by nucleophilic substitution on the 1,2,3-triazole ring and by 1,3-dipolar cycloaddition of azides to selected alkynes and to phenylacetone. The new compounds tested on rat aortic rings did not exhibit any significant vasorelaxing activity.

  DOI：

  10.1016/j.farmac.2005.03.004

文献信息

• Synthesis and Biological Evaluation of Small Molecules as Potential Anticancer Multitarget Agents
  作者：Alberto Pla-López、Raquel Castillo、Rocío Cejudo-Marín、Olaya García-Pedrero、Mariam Bakir-Laso、Eva Falomir、Miguel Carda

  DOI：10.3390/ijms23137049

  日期：——

  determined. The effects on the abovementioned biological targets were evaluated for some selected compounds. Compound 23, bearing a p-chlorophenyl group, showed better results than sorafenib in regard to the downregulation of VEGFR-2 and a similar effect to BMS-8 on both PD-L1 and c-Myc proteins. The antiangiogenic and antivascular activities of chloro derivatives were also established by endothelial microtube

  设计了 26 种基于三唑的衍生物，用于靶向 PD-L1（程序性死亡受体配体 1）和 VEGFR-2（血管内皮生长因子受体 2）。这些化合物被合成和生物学评估为 VEGFR-2、PD-L1 和 c-Myc 蛋白的多靶点抑制剂。测定了这些分子对几种肿瘤细胞系（HT-29、A-549 和 MCF-7）和非肿瘤细胞系 HEK-293 的抗增殖活性。对一些选定的化合物对上述生物靶点的影响进行了评估。化合物23 ,轴承-氯苯基组在下调 VEGFR-2 方面显示出比索拉非尼更好的结果，并且与 BMS-8 对 PD-L1 和 c-Myc 蛋白的作用相似。氯代衍生物的抗血管生成和抗血管活性也通过 Matrigel ®上的内皮微管形成试验确定。
• Tetracopper(<scp>i</scp>) thiolate- and amido-(SNS) complexes and copper-catalyzed azide–alkyne cycloaddition in water
  作者：Atousa Khanzadeh、Saeed Ataie、R. Tom Baker

  DOI：10.1039/d3dt01651j

  日期：——

  diffraction and mass spectrometry. Although the amido ligand undergoes irreversible N-protonation by the copper-bound alkyne, the thiolate complex demonstrates good activity in the copper-catalyzed azide–alkyne cycloaddition reaction with a variety of substrates. The base-free reactions are performed in water and afford excellent yields over 2 h at 70 °C. DFT calculations suggest a proton-shuttle role

  通过 X 射线衍射和质谱法对两种带有硫醇盐和酰胺基 SNS 配体的四核 Cu( I ) 配合物进行了表征。尽管酰胺配体通过铜键合的炔发生不可逆的N-质子化，但硫醇盐络合物在铜催化的叠氮化物-炔与各种底物的环加成反应中表现出良好的活性。无碱反应在水中进行，在 70 °C 下 2 小时内可获得优异的产率。DFT 计算表明硫醇盐供体在初始二铜 σ,π-炔基中间体的形成中发挥质子穿梭作用。