7,8-dimethoxy-2,3-dihydrochromen-4-one | 19149-07-6

• 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: 7,8-dimethoxy-2,3-dihydrochromen-4-one
• 英文别名: 7,8-dimethoxychroman-4-one；7,8-dimethoxychromanone；7,8-dimethoxy-chroman-4-one；7,8-Dimethoxy-chroman-4-on；7,8-dimethoxy-4-chromanone；7,8-Dimethoxy-4-chromanon
• CAS: 19149-07-6
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: XDKDVWJTTMLLDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,8-dimethoxy-2,3-dihydrochromen-4-one 在 pyridinium hydrobromide perbromide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.67h， 以48%的产率得到3-bromo-7,8-dimethoxy-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  Synthesis of Rigidified eIF4E/eIF4G Inhibitor-1 (4EGI-1) Mimetic and Their in Vitro Characterization as Inhibitors of Protein–Protein Interaction

  摘要：

  The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro characterization of a series of rigidified mimetic of this prototypic inhibitor in which the phenyl in the 2-(4-(3,4-dichlorophenyl)thiazol-2-yl) moiety was bridged into a tricyclic system. The bridge consisted one of the following: ethylene, methylene oxide, methylenesulfide, methylenesulfoxide, and methylenesulfone. Numerous analogues in this series were found to be markedly more potent than the parent prototypic inhibitor in the inhibition of eIF4E/eIF4G interaction, thus preventing the eIF4F complex formation, a rate limiting step in the translation initiation cascade in eukaryotes, and in inhibition of human cancer cell proliferation.

  DOI：

  10.1021/jm401733v
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 溶剂黄146 、 铂 作用下， 生成 7,8-dimethoxy-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  Pfeiffer; Emmer, Chemische Berichte, 1920, vol. 53, p. 949

  摘要：

  DOI：

文献信息

• Aminomethyl-chroman compounds
  申请人：Abbott Laboratories

  公开号：US05089519A1

  公开（公告）日：1992-02-18

  The present invention includes compounds represented by the formula: ##STR1## wherein X is O or S; R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, hydroxy, halo, loweralkoxy, thioalkoxy and loweralkyl; or R.sub.1 and R.sub.2 taken together can form a methylenedioxy or ethylenedioxy bridge; R.sub.3 is loweralkyl; R.sub.4 is selected from ##STR2## wherein Y is O or S, R.sub.6 is hydrogen, methoxy or halo and m is 0 or 1; R.sub.5 is hydrogen, loweralkyl, phenyl or substituted phenyl wherein the phenyl ring is substituted with one, two or three substituents independently selected from loweralkyl, halo, hydroxy, loweralkoxy, amino and thioalkoxy; and R.sub.8 is hydrogen or R.sub.3 and R.sub.8 taken together form a pyrrolidine ring; or a pharmaceutically acceptable salt thereof.

  本发明包括由以下式表示的化合物：##STR1## 其中X为O或S；R.sub.1和R.sub.2分别选自氢、羟基、卤、低烷氧基、硫代烷氧基和低烷基的群；或R.sub.1和R.sub.2一起可以形成一个亚甲二氧桥或乙烯二氧桥；R.sub.3为低烷基；R.sub.4选自##STR2## 其中Y为O或S，R.sub.6为氢、甲氧基或卤，m为0或1；R.sub.5为氢、低烷基、苯基或取代苯基，其中苯环上取代基可独立选自低烷基、卤、羟基、低烷氧基、氨基和硫代烷氧基；R.sub.8为氢或R.sub.3和R.sub.8一起形成吡咯烷环；或其药学上可接受的盐。
• Aminomethyl-chroman and -thiochroman compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0325964A1

  公开（公告）日：1989-08-02

  The present invention includes compounds represented by the formula: wherein X is O or S; R₁ and R₂ are independently selected from the group consisting of hydrogen, hydroxy, halo, loweralkoxy, thioalkoxy and loweralkyl; or R₁ and R₂ taken together can form a methylenedioxy or ethylenedioxy bridge; R₃ is loweralkyl; R₄ is selected from wherein Y is O or S, R₆ is hydrogen, methoxy or halo and m is 0 or 1; R₅ is hydrogen, loweralkyl, phenyl or substituted phenyl wherein the phenyl ring is substituted with one, two or three substituents independently selected from loweralkyl, halo, hydroxy, loweralkoxy, amino and thioalkoxy; and R₈ is hydrogen or R₃ and R₈ taken together form a pyrrolidine ring; or a pharmaceutically acceptable salt thereof.

  本发明包括由式表示的化合物： 其中 X 是 O 或 S； R₁和R₂独立地选自氢、羟基、卤代、低级烷氧基、硫代烷氧基和低级烷基组成的组；或R₁和R₂合在一起可形成亚甲二氧基或亚乙二氧基桥； R₃ 是低级烷基； R₄ 选自 其中 Y 为 O 或 S，R₆ 为氢、甲氧基或卤代，m 为 0 或 1； R₅ 是氢、低级烷基、苯基或取代苯基，其中苯基环被独立选自低级烷基、卤代、羟基、低级烷氧基、氨基和硫代烷氧基的一个、两个或三个取代基取代；以及 R₈ 是氢或 R₃ 和 R₈ 共同形成吡咯烷环；或其药学上可接受的盐。
• Pfeiffer et al., Journal fur praktische Chemie (Leipzig 1954), 1931, vol. <2> 129, p. 31,37
  作者：Pfeiffer et al.

  DOI：——

  日期：——
• Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of .alpha.1 and .alpha.2 adrenergic activities
  作者：John F. DeBernardis、Martin Winn、David L. Arendsen、Daniel J. Kerkman、John J. Kyncl

  DOI：10.1021/jm00158a016

  日期：1986.8

  A series of modifications to positions 1, 2, and 4 of the tetralin ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin (1, A-54741) succeeded in improving the separation of the potent alpha 1 and alpha 2 adrenergic agonism observed for the parent compound 1. In particular 5,6-dihydroxy-4,4-dimethyl-1-(2-imidazolinyl)tetralin (7) was found to be a specific alpha 1 adrenergic agonist, and 7,8-dihydroxy-4-(2-imidazolinyl)chroman (2) was found to have improved alpha 2 adrenergic agonistic selectivity relative to the parent compound 1.
• Pfeiffer; Oberlin; Konermann, Chemische Berichte, 1925, vol. 58, p. 1955
  作者：Pfeiffer、Oberlin、Konermann

  DOI：——

  日期：——