methyl 1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate | 141072-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate
• 英文别名: methyl 1-[(4-methoxyphenyl)methyl]triazole-4-carboxylate
• CAS: 141072-06-2
• 化学式: C₁₂H₁₃N₃O₃
• mdl: MFCD03866366
• 分子量: 247.254
• InChiKey: VOHUPXZJEWOFKS-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C
• 沸点：
  419.5±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)carbohydrazide
  参考文献：
  名称：

  Design and development of Isatin-triazole hydrazones as potential inhibitors of microtubule affinity-regulating kinase 4 for the therapeutic management of cell proliferation and metastasis

  摘要：

  Microtubule affinity-regulating kinase 4 (MARK4) is a potential drug target as the same is found to be over expressed in several types of cancers. In search of effective MARK4 inhibitors, we have synthesized and characterized Isatin-triazole hydrazones (9a-i) and evaluated their inhibitory potential. Of all the compounds, 9g showed better binding affinity and enzyme inhibition potential in sub micromolar range. Human serum albumin (HSA) binding assay suggested an easy transportation of 9g in blood stream due to its binding affinity. In vitro anticancer studies performed on MCF-7, MDA-MB-435s and HepG2 cells using 9g showed inhibition of cell proliferation and cell migration. Further, 9g induces apoptosis in these cancerous cells, with IC50 values of 6.22, 9.94 and 8.14 mu M, respectively. Putatively, 9g seems to cause oxidative stress resulting in apoptosis. Functional assay of 9g with a panel of 26 kinases showed MARK4 specific profile. In conclusion, 9g seems to possess an effective inhibitory potential towards MARK4 adding an additional repertoire to anticancer therapeutics. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.12.026
• 作为产物：
  描述：

  4-甲氧基苄醇 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 三溴化磷 、 sodium ascorbate 作用下， 以 乙醚 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 24.0h， 生成 methyl 1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  合成与1-苄基-生物评价ñ - （2-（苯基氨基）吡啶-3-基）-1- ħ 1,2,3-三唑-4-甲酰胺作为抗有丝分裂剂

  摘要：

  1-苄基-甲库ñ - （2-（苯基氨基）吡啶-3-基）-1- ħ 1,2,3-三唑-4-甲酰胺（图7a-人）已经被设计，合成和筛选其对某些选定的人类癌细胞系DU-145，A-549，MCF-7和HeLa具有抗增殖活性。它们中的大多数已显示出对肺癌细胞系（A549）的有希望的细胞毒性，其中7f被发现是最有效的抗增殖同源物。此外，7f表现出与 标准E7010（IC 50值为2.15）相当的微管蛋白聚合抑制作用（IC 50值为2.04 µM）。 µM）。此外，流式细胞仪分析表明该化合物通过在A549细胞中以G 2 / M期的细胞周期停滞来诱导凋亡。通过检查线粒体膜电位进一步观察到了细胞凋亡的诱导，并且通过Hoechst染色以及膜联蛋白V-FITC分析也证实了凋亡的诱导。此外，分子对接研究表明化合物7f与β-微管蛋白的秋水仙碱结合位点结合。因此，7f通过在秋水仙碱活性位点的结合抑制微管蛋白聚合并诱导细胞凋亡而表现出抗增殖特性。

  DOI：

  10.1016/j.bioorg.2018.11.002

文献信息

• Efficient Synthesis of 5-Trifluoromethylthio-1,2,3-Triazoles: One-Pot Multicomponent Reaction from Elemental Sulfur and TMSCF3
  作者：Lin-Lin Zhang、Meng-Tian Li、Liang-Liang Shen、Qin-Pei Wu

  DOI：10.1055/s-0039-1690716

  日期：2020.1

  A sequential multistep reaction toward 5-trifluoromethyl­thio-1,2,3-triazoles has been established, starting from alkynes, organo­azides, S8, and (trifluoromethyl)trimethylsilane (TMSCF3). This reaction features mild conditions, easy operation, and readily available substrates.

  从炔烃，有机叠氮化物，S 8和（三氟甲基）三甲基硅烷（TMSCF 3）开始，已经建立了针对5-三氟甲硫基-1,2,3-三唑的顺序多步反应。该反应具有条件温和，易于操作和易于获得的底物的特点。
• SUBSTITUTED TRIAZOLOPHTHALAZINE DERIVATIVES
  申请人：Harbeson Scott L.

  公开号：US20110172235A1

  公开（公告）日：2011-07-14

  This invention relates to novel substituted triazolophthalazines and pharmaceutically acceptable salts thereof. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering selective α5 receptor partial or full inverse agonists.

  本发明涉及新型取代的三唑喹噁啉及其药学上可接受的盐。本发明还提供了包含本发明化合物的组合物，并将这种组合物用于治疗通过给予选择性α5受体部分或全反向激动剂有益治疗的疾病和病症的方法。
• Abu-Orabi, Sultan T.; Atfah, Adnan; Jibril, Ibrahim, Gazzetta Chimica Italiana, 1992, vol. 122, # 1, p. 29 - 33
  作者：Abu-Orabi, Sultan T.、Atfah, Adnan、Jibril, Ibrahim、Al-Sheikh Ali, Amer、Marii, Fakhri

  DOI：——

  日期：——
• Catalytic Cyclization of 2,3-Dibromopropionates with Benzyl Azides to Afford 1-Benzyl-1,2,3-triazole-4-carboxylate: The Use of a Nontoxic Bismuth Catalyst
  作者：Hong-bin Sun、Dong Li、Weiping Xie、Xinlin Deng

  DOI：10.3987/com-15-13371

  日期：——

  We synthesized 1,2,3-triazoles via the cyclization of 2,3-dibromopropionates with benzyl azides. Bismuth chloride is an efficient catalyst, and the reaction is accelerated by weak bases such as sodium acetate. A variety of functional groups are compatible with this catalytic protocol, and it takes advantage of oxygen stable catalyst and substrates because the reactive dibromides are saturated.
• US8557815B2
  申请人：——

  公开号：US8557815B2

  公开（公告）日：2013-10-15