4-hydroxy-6-(3-methoxy-phenyl)-pyrane-2-one | 220633-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-hydroxy-6-(3-methoxy-phenyl)-pyrane-2-one
• 英文别名: 4-Hydroxy-6-(3-methoxyphenyl)-2H-pyran-2-one；4-hydroxy-6-(3-methoxyphenyl)pyran-2-one
• CAS: 220633-46-5
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: AGTNGHTYOYXPFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲基-2-丁烯醛 、 4-hydroxy-6-(3-methoxy-phenyl)-pyrane-2-one 在 哌啶 、 乙酸酐 作用下， 以 乙酸乙酯 为溶剂， 以82%的产率得到7-(3-Methoxy-phenyl)-2,2-dimethyl-2H-pyrano[4,3-b]pyran-5-one
  参考文献：
  名称：

  Sequential 1,2-Addition−Electrocyclic Ring Closures Involving Acyclic α,β-Unsaturated Iminiums:  A Formal [3 + 3] Cycloaddition Strategy to Unique Pyranyl Spirocycles

  摘要：

  DOI：

  10.1021/jo982165k
• 作为产物：
  描述：

  3-甲氧基苯甲酸甲酯 在 四甲基乙二胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， -78.0~150.0 ℃ 、399.97 Pa 条件下， 生成 4-hydroxy-6-(3-methoxy-phenyl)-pyrane-2-one
  参考文献：
  名称：

  Synthesis and UV Studies of A Small Library of 6-Aryl-4-hydroxy-2-pyrones. A Relevant Structural Feature for the Inhibitory Property of Arisugacin Against Acetylcholinesterase

  摘要：

  4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that ale biologically relevant. We describe here preparations of a small library of 6-aryl-4-hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy-pyrones are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00847-9

文献信息

• [EN] SUBSTITUTED 1H-PYRIDINE-2-ONE DERIVATIVES<br/>[FR] DERIVES DE 1H-PYRIDINE-2-ONE SUBSTITUEE
  申请人：C & C RES LAB

  公开号：WO2004050624A1

  公开（公告）日：2004-06-17

  The present invention relates to substituted 1H-pyridine-2-one derivatives of formula (1) and pharmaceutically acceptable salts thereof, which are useful for the treatment of chronic obstructive pulmonary disease, asthma, chronic bronchitis, psoriasis, ulcerative colitis, Crohn's disease (local ileitis), arteriosclerosis, rheumatoid arthritis, osteoporosis, bone arthritis, depression, memory loss, inflammation mediated by chronic necrosis and the others mediated by PDE4: (I)

  本发明涉及式（1）的取代1H-吡啶-2-酮衍生物及其药学上可接受的盐，用于治疗慢性阻塞性肺疾病、哮喘、慢性支气管炎、牛皮癣、溃疡性结肠炎、克罗恩病（局部回肠炎）、动脉硬化、类风湿性关节炎、骨质疏松症、骨关节炎、抑郁症、记忆力丧失、由慢性坏死介导的炎症以及其他由PDE4介导的炎症：（I）
• Antitumor agents 270. Novel substituted 6-phenyl-4H-furo[3,2-c]pyran-4-one derivatives as potent and highly selective anti-breast cancer agents
  作者：Yizhou Dong、Qian Shi、Kyoko Nakagawa-Goto、Pei-Chi Wu、Susan L. Morris-Natschke、Arnold Brossi、Kenneth F. Bastow、Jing-Yu Lang、Mien-Chie Hung、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2009.11.049

  日期：2010.1

  synthesized and evaluated as novel anti-breast cancer agents. Compounds 10–13, 23, 25, and 27 showed potent inhibition against the SK-BR-3 breast cancer cell line. Importantly, 25 and 27 showed the highest cancer cell line selectivity, being approximately 100–250-fold more potent against SK-BR-3 (ED50 0.28 and 0.44 μM, respectively) compared with other cancer cell lines tested. In addition, 25 displayed

  6-Phenyl-4 H -furo [3,2 - c ]pyran-4-one 衍生物基于新 tashinlactone ( 1 ) 被合成并评估为新型抗乳腺癌药物。化合物10-13，23，25，和27显示出针对SK-BR-3乳腺癌细胞系有效抑制。重要的是，25和27显示出最高的癌细胞系选择性，与其他测试的癌细胞系相比，对 SK-BR-3（ED 50分别为 0.28 和 0.44 μM）的效力大约高出 100-250 倍。此外，25对正常乳腺细胞系 184A1 和 MCF10A 显示出低细胞毒性。化合物25和27值得在我们持续的项目中进一步研究，以生成和开发选择性抗乳腺癌药物。
• AMINOMETHYLENE DERIVATIVES AND ULTRAVIOLET ABSORBER COMPRISING THE SAME
  申请人：CHEMIPRO KASEI KAISHA, LIMITED

  公开号：EP0950655A1

  公开（公告）日：1999-10-20

  The present invention provides an aminomethylene derivative represented by general formula (I): wherein A is a cyclic oxo group selected from the group consisting of following general formulae (a), (b), (c), (d) and (e): wherein R1, R2, R3, R4 and R5 each independently represent H, an alkyl group or the like; R6, R7 and R8 each independently represent an alkyl group or the like; R1 and R2 or R7 and R8 may combine with each other to form a tetramethylene group or the like; R represents an alkyl group optionally containing OH or O; and n is an integer of 0 to 4, a process for the same, and the use thereof. The derivatives have an excellent ultraviolet absorption ability and a high optical stability.

  本发明提供一种由通式(I)表示的亚氨基亚甲基衍生物： 其中 A 是选自以下通式（a）、（b）、（c）、（d）和（e）所组成的组的环状氧代基团： 其中 R1、R2、R3、R4 和 R5 各自独立地代表 H、烷基或类似基团；R6、R7 和 R8 各自独立地代表烷基或类似基团；R1 和 R2 或 R7 和 R8 可相互结合形成四亚甲基或类似基团；R 代表任选含有 OH 或 O 的烷基；n 为 0 至 4 的整数。这些衍生物具有出色的紫外线吸收能力和较高的光学稳定性。
• Sequential 1,2-Addition−Electrocyclic Ring Closures Involving Acyclic α,β-Unsaturated Iminiums:  A Formal [3 + 3] Cycloaddition Strategy to Unique Pyranyl Spirocycles
  作者：Richard P. Hsung、Hong C. Shen、Christopher J. Douglas、Christopher D. Morgan、Shane J. Degen、Letitia J. Yao

  DOI：10.1021/jo982165k

  日期：1999.2.1
• US6114546A
  申请人：——

  公开号：US6114546A

  公开（公告）日：2000-09-05