2-(2-benzoxazolyl)quinoxaline | 24613-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(2-benzoxazolyl)quinoxaline
• 英文别名: 2-(1,3-benzoxazol-2-yl)quinoxaline；2-(quinoxalin-2-yl)benzoxazole；2-(Benzoxazol-2'-yl)-chinoxalin；2-benzooxazol-2-yl-quinoxaline；2-(Quinoxalin-2-yl)benzo[d]oxazole；2-quinoxalin-2-yl-1,3-benzoxazole
• CAS: 24613-98-7
• 化学式: C₁₅H₉N₃O
• 分子量: 247.256
• InChiKey: RAFKTGWINPUNBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  412.3±30.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P270,P301+P312,P330,P501
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  2-(2-benzoxazolyl)quinoxaline 、 trifluoromethylbicyclo [1.1.1]pentyl thianthrenium salt 在 potassium permanganate 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以49 %的产率得到2-(3-(3-(trifluoromethyl)bicyclo[1.1.1]pentan-1-yl)quinoxalin-2-yl)benzo[d]oxazole
  参考文献：
  名称：

  BCP-铊盐的 EDA 络合物：一种获取 1-三氟甲基-3-喹喔啉衍生物双环[1.1.1]戊烷的无催化剂策略

  摘要：

  第一个例子使用BCP铊盐构建EDA络合物，提供了一种无催化剂且温和的方案，在光诱导条件下高产率获得1-三氟甲基-3-喹喔啉衍生物双环[1.1.1]戊烷（36个例子） ，对生物活性分子衍生物的结构修饰也成功实现。

  DOI：

  10.1002/ejoc.202400386
• 作为产物：
  描述：

  2-喹喔啉甲醛 、 2-氨基苯酚 在 silica chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以74%的产率得到2-(2-benzoxazolyl)quinoxaline
  参考文献：
  名称：

  In-vitro Anti-cancer assay and apoptotic cell pathway of newly synthesized benzoxazole-N-heterocyclic hybrids as potent tyrosine kinase inhibitors

  摘要：

  A series of benzoxazole-N-heterocyclic hybrids have been synthesized by a one-pot strategy. Molecular docking study revealed that such compounds have the ability to inhibit enzyme protein tyrosine kinase. The findings of this work have been the successful synthesis of benzoxazole scaffolds, featuring hybrids of benzoxazole with quinoline and quinoxaline respectively. The molecular docking studies have showed these compounds to be inhibitors of tyrosine kinase enzyme which triggers growth of cancer cells. The cytotoxicity study of compounds 4a-f showed better potency against breast cancer cell lines MCF-7 and MDA-MB-231 in contrast to oral and lung cancer cell lines KB and A549. The tyrosine kinase activity was measured using Universal Tyrosine Kinase Assay kit using horseradish peroxide (HRP)-conjugated anti-phosphotyrosine kinase solution as a substrate. The compounds 4c exhibited maximum inhibition in the activity of enzyme tyrosine kinase with IC50 value 0.10 +/- 0.16 mu M, than other compounds which were studied and thus proved to be inhibitors of enzyme tyrosine kinase. The selective index of all four compounds was found out to be greater than two, indicating the non-toxic behaviour, i.e. good anti-cancer activity. Further, fluorescence microscopic study helped to characterize the mode of cell death, which was found to be late apoptosis as indicated by the orange fluorescence. The SAR analysis has also been carried out.

  DOI：

  10.1016/j.bioorg.2019.103382

文献信息

• Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles <i>via</i> redox condensation of <i>o</i>-nitrophenols with acetophenones and methylquinolines
  作者：Le Anh Nguyen、Thi Thu Tram Nguyen、Quoc Anh Ngo、Thanh Binh Nguyen

  DOI：10.1039/d1ob00976a

  日期：——

  An Fe/S catalyst generated in situ from FeCl2·4H2O and elemental sulfur S8 in the presence of a tertiary amine as a base was found to catalyze efficiently a 6e− redox condensation of o-nitrophenols with acetophenones and methylquinolines. The condensed products 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles were obtained in reasonable yields with water as the only byproduct at a temperature as low

  发现在叔胺作为碱存在下由 FeCl 2 ·4H 2 O 和元素硫 S 8原位生成的 Fe/S 催化剂可有效催化邻硝基苯酚与苯乙酮和甲基喹啉的 6e -氧化还原缩合反应。缩合产物 2-苯甲酰基苯并恶唑和 2-喹啉基苯并恶唑在低至 80 °C 的温度下以合理的收率获得，水作为唯一的副产物。
• [EN] NOVEL QUINOLINE-CARBAXAMIDES AS JACK3 KINASE MODULATORS<br/>[FR] NOUVEAUX QUINOLEINE-CARBAXAMIDES EN TANT QUE MODULATEURS DE JACK3 KINASE
  申请人：ASTRAZENECA AB

  公开号：WO2005075429A1

  公开（公告）日：2005-08-18

  The present invention relates to novel compounds which are JAK3 Kinase inhibitors, methods for their preparation and pharmaceutical compositions comprising them. A compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof, wherein X is -CHOH or -C=O;

  本发明涉及一种新型化合物，它们是JAK3激酶抑制剂，以及其制备方法和包含它们的药物组合物。式（I）的化合物或其药用可接受的盐或溶剂，其中X为-CHOH或-C=O。
• Base-Promoted Cross-Dehydrogenative Coupling of Quinoline <i>N</i>-Oxides with 1,3-Azoles
  作者：Xiaopei Chen、Xiuling Cui、Fangfang Yang、Yangjie Wu

  DOI：10.1021/acs.orglett.5b00330

  日期：2015.3.20

  An efficient cross-dehydrogenative coupling of quinoline N-oxides and 1,3-azoles has been developed under external oxidant and metal free conditions. The desired products were isolated in good to excellent yields for 26 examples. This methodology provides a practical pathway to biheteroaryls and features high practicality, high efficiency, and environmental friendliness.
• Synthesis and investigation of some connected heterocyclic systems
  作者：A. L. Gershuns、A. N. Brizitskaya

  DOI：10.1007/bf00470275

  日期：——
• NOVEL QUINOLINE-CARBAXAMIDES AS JACK3 KINASE MODULATORS
  申请人：AstraZeneca AB

  公开号：EP1718615A1

  公开（公告）日：2006-11-08