1-(2-imino-8-methoxy-2H-chromen-3-yl)pyridinium chloride | 1236145-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-(2-imino-8-methoxy-2H-chromen-3-yl)pyridinium chloride
• 英文别名: 1-(2-imino-2H-chromen-3-yl)pyridinium chloride
• CAS: 1236145-29-1
• 化学式: C₁₅H₁₃N₂O₂*Cl
• 分子量: 288.733
• InChiKey: SZRNCTKAKFDRCY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.1
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2-imino-8-methoxy-2H-chromen-3-yl)pyridinium chloride 在 三乙烯二胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以63%的产率得到4-methoxy-12H-chromeno[2',3':4,5]imidazo-[1,2-a]pyridin-12-one
  参考文献：
  名称：

  某些咪唑并吡啶稠合色酮的选择性合成

  摘要：

  通过一锅法合成了结合有咪唑并[1,2- a ]吡啶和取代的色酮的稠合杂环支架。该反应通过在乙醇中和在DABCO存在下将1-（2-亚氨基-2 H-铬-3-基）吡啶鎓氯化物进行分子内环化而进行。对实验条件的详细研究可以清楚地了解反应途径。

  DOI：

  10.1016/j.tet.2011.09.054
• 作为产物：
  描述：

  N-(氰甲基)氯化吡啶 、 邻香草醛 在 N-甲基哌嗪 作用下， 以 乙醇 、 丙酮 为溶剂， 以78%的产率得到1-(2-imino-8-methoxy-2H-chromen-3-yl)pyridinium chloride
  参考文献：
  名称：

  一锅法在水性介质中合成新型12 H -chromeno [2'，3'：4,5]咪唑并[1,2- a ]吡啶

  摘要：

  在包含水杨醛和1-（氰甲基）吡啶鎓氯化物的一锅缩合/环化反应中，在碳酸钠水溶液中生成了铬诺-咪唑并[1,2- a ]吡啶骨架。这些新型化合物的分离产率为47-71％。反应路径之后是1 H NMR光谱，可以清楚地了解该过程中涉及的副反应。 合成了不同的单取代吡啶鎓氯化物，并使其与单取代水杨醛反应，并对该合成方法的范围进行了详细讨论。

  DOI：

  10.1016/j.tet.2010.04.059

文献信息

• [EN] CHROMENE-BASED COMPOUNDS, METHODS AND USES THEREOF<br/>[FR] COMPOSÉS À BASE DE CHROMÈNE, LEURS PROCÉDÉS ET UTILISATIONS
  申请人：UNIV DO MINHO

  公开号：WO2020261242A1

  公开（公告）日：2020-12-30

  The present disclosure relates to a compound or a pharmaceutically acceptable salt, hydrate, solvate, N -oxide, stereoisomer, diastereoisomer, enantiomer, atropisomer, dimer, or polymorph for use in medicine comprising the following formula (I): wherein R1, R2 and R3 are independently selected from each other; R1 is selected from an aryl, or heterocyclic ring; R2 is selected from a H, alkyl, aryl, alcoxyl, halogen, hydroxyl, amine, carbonyl, or heterocyclic ring; R3 is selected from a H, or (II).

  本公开涉及一种化合物或药用可接受的盐、水合物、溶剂合物、N-氧化物、立体异构体、顺反异构体、对映异构体、对映异构体、二聚体或多晶形式，用于药物，其化学式如下（I）：其中R1、R2和R3是彼此独立选择的；R1选择自芳基或杂环环；R2选择自H、烷基、芳基、醚基、卤素、羟基、胺基、酮基或杂环环；R3选择自H或（II）。
• Synthesis of 2-aminochromene derivatives from 1-(2-imino-2H-chromen-3-yl)pyridin-1-ium perchlorates and nitromethane in basic medium
  作者：Olga А. Storozhenko、Xiaoyi Yue、Alexey А. Festa、Alexey А. Varlamov、Leonid G. Voskressensky

  DOI：10.1007/s10593-020-02793-3

  日期：2020.9

  1-(2-imino-2H-chromen-3-yl)pyridinium perchlorates and nitromethane by the action of DBU at reflux in trifluoroethanol. The starting 2-iminochromenes are readily accessible from the corresponding salicylic aldehydes and quaternary cyanomethyl pyridinium salts. The reaction is tolerant to substituents of different nature (alkyl, alkoxy, halogen); a limitation is the presence of strong electron-withdrawing substituents

  新的2-氨基-4-（nitromethylidene）色烯1-（2-亚氨基2的反应的结果，获得ħ -苯并吡喃-3-基）的三氟乙醇吡啶鎓高氯酸盐和硝基甲烷通过DBU的作用在回流。起始的2-亚氨基色酮易于从相应的水杨醛和季氰基甲基吡啶鎓盐获得。该反应可耐受不同性质的取代基（烷基，烷氧基，卤素）；局限性是在色烯的苯环中存在强的吸电子取代基。在反应过程中，产物沉淀并且可以通过过滤分离。
• Synthesis of 3-aminochromenes: the Zincke reaction revisited
  作者：Marta Costa、Ana I. Rodrigues、Fernanda Proença

  DOI：10.1016/j.tet.2014.05.074

  日期：2014.8

  3-Aminocoumarines and 2-iminochromen-3-amines were efficiently prepared from the Zincke-ring-opening reaction of the corresponding 2H-chromen-3-pyridinium chlorides using N-methylpiperazine. This methodology unravels the marked potential of pyridinium salts as protective groups for primary amines. These scaffolds can be considered important building blocks for new novobiocin analogues and heterocyclic

  使用N-甲基哌嗪，由相应的2 H-氧化铬3-吡啶鎓氯化物的Zincke开环反应，可以有效地制备3-氨基香豆素和2-亚氨基氧化铬3-胺。该方法揭示了吡啶鎓盐作为伯胺保护基的显着潜力。 这些支架可以被认为是新生物素类似物和杂环化合物的重要组成部分。
• Novel structurally similar chromene derivatives with opposing effects on p53 and apoptosis mechanisms in colorectal HCT116 cancer cells
  作者：Cristovao F. Lima、Marta Costa、M.F. Proença、Cristina Pereira-Wilson

  DOI：10.1016/j.ejps.2015.02.019

  日期：2015.5

  In the present work, novel chromene derivatives fused with the imidazo[1,2-a]pyridine nucleus were tested for their anticancer potential in the human colorectal cancer HCT116 cells. Compounds 2a and 2c showed significant growth inhibitory activity with GI50 of 15 mu M and 11 mu M, respectively. Compound 2c, the most potent, has a carbamate group in position 8 of the pyridine ring, and showed significant cell cycle arrest and induction of cell death by apoptosis, even at 51xM. Besides different potencies, chromene analogs 2a and 2c showed different mechanisms of action. Whereas the carbamate-free chromene 2a induced cell cycle arrest at GI /G0 phase, compound 2c showed to arrest cell cycle at both S and G2 phases. Chromene derivative 2a at concentrations higher than its GI50 remarkably induced caspases-dependent apoptosis in a p53-independent manner. On the other hand, compound 2c increased significantly p53 levels and induced apoptosis in a p53- and caspases-dependent manner, even at concentrations lower than its GI50. Both compounds increased the Bax/Bcl-2 ratio, induced mitochondria depolarization and activated MAP kinases. In conclusion, two novel and structurally similar chromene derivatives showed cytotoxicity to HCT16 cells through opposing effects on p53 levels and apoptosis mechanisms, which may be relevant for further development of drugs acting on distinct molecular targets useful in the treatment of cancers with different genetic profiles and for personalized medicine. (C) 2015 Elsevier B.V. All rights reserved.