4H-1-苯并吡喃-4-酮,7-羟基-3-(3-甲氧苯基)- | 139256-06-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 4H-1-苯并吡喃-4-酮,7-羟基-3-(3-甲氧苯基)-
• 英文名称: 7-hydroxy-3-(3-methoxyphenyl)-4H-chromen-4-one
• 英文别名: 7-hydroxy-3'-methoxyisoflavone；indigoferone；7-Hydroxy-3-(3-methoxy-phenyl)-chromen-4-one；7-hydroxy-3-(3-methoxyphenyl)chromen-4-one
• CAS: 139256-06-7
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: SVIVXHGAPCFWCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4H-1-苯并吡喃-4-酮,7-羟基-3-(3-甲氧苯基)- 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 生成 2,2-dimethyl-propanoic acid 3,4-dihydro-3-(3-methoxyphenyl)-4-oxo-2H-1-benzopyran-7-yl ester
  参考文献：
  名称：

  Synthesis, pharmacological evaluation, and structure–activity relationships of benzopyran derivatives with potent SERM activity

  摘要：

  The synthesis, binding affinity for estrogen receptor subtypes (ERalpha and ERbeta) and pharmacological activity on rat uterus of a new class of potent ligands, characterized by a 3-phenylbenzopyran scaffold with a basic side chain in position 4, are reported. Some of these compounds, endowed with very high receptor affinity, showed potent inhibition of agonist-stimulated uterine growth, with no or limited proliferative effect. Binding affinity mostly depended on the nature and position of substituents at the 3-phenyl ring, while the uterine activity seems to be affected by basic chain length. Compound 9c (CHF4227) showed excellent binding affinity and antagonist activity on the uterus. The docking of benzopyran derivatives explained the structure-affinity relationships observed for 3-phenyl substitution: a small, hydrophobic 4'-substituent could interact with a small accessory binding cavity, while di-substitution at 4' and 3' led to some ERalpha selectivity. This selectivity can be ascribed to differences in amino acid composition and side chain conformation in the region accommodating the 3-phenyl ring at human ERalpha and ERbeta ligand-binding domain. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.015
• 作为产物：
  描述：

  3-甲氧基苯乙酸 在 三氟化硼乙醚 、 甲基磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4H-1-苯并吡喃-4-酮,7-羟基-3-(3-甲氧苯基)-
  参考文献：
  名称：

  Waehaelae, Kristiina; Hase, Tapio A., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3005 - 3008

  摘要：

  DOI：

文献信息

• Benzoxazepine derivatives as selective estrogen receptor modulators
  申请人：Lanter C. James

  公开号：US20060040917A1

  公开（公告）日：2006-02-23

  The present invention is directed to novel benzoxazepine derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and diseases mediated by an estrogen receptor.

  本发明涉及新型苯并噁唑啉衍生物，含有它们的药物组合物以及它们在治疗由雌激素受体介导的疾病和疾病中的应用。
• 7-Hydroxy-benzopyran-4-one Derivatives: A Novel Pharmacophore of Peroxisome Proliferator-Activated Receptor α and -γ (PPARα and γ) Dual Agonists
  作者：Azadeh Matin、Navnath Gavande、Moon S. Kim、Nancy X. Yang、Noeris K. Salam、Jane R. Hanrahan、Rebecca H. Roubin、David E. Hibbs

  DOI：10.1021/jm900964r

  日期：2009.11.12

  Design, synthesis, and in vitro bioevaluation of a new class of potential dual PPARα and γ agonists discovered through a structure-driven design paradigm are described. The 7-hydroxy-benzopyran-4-one moiety (includes flavones, flavanones, and isoflavones) is the key pharmacophore of these novel molecules, exhibiting similarity to the core structure of both fibrates and thiazolidinediones. New lead

  描述了通过结构驱动设计范式发现的新型潜在的双重PPARα和γ双重激动剂的设计，合成和体外生物评价。7-羟基-苯并吡喃-4-酮部分（包括黄酮，黄烷酮和异黄酮）是这些新分子的关键药效​​基团，与贝特类药物和噻唑烷二酮的核心结构相似。从“保健食品”和合成类似物中鉴定出新的PPAR配体。总共筛选了77个分子，包括查耳酮，黄酮，黄烷酮，异黄酮和吡唑衍生物，并进行了双重激动剂的构效关系研究。化合物68，70，72，和76被鉴定为新型有效的PPARα和γ双重激动剂。这些新型分子可能会成为PPAR相关疾病（包括II型糖尿病和代谢综合征）未来的领先者。
• Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
  作者：Jianzhuang Miao、Huaqing Cui、Jing Jin、Fangfang Lai、Hui Wen、Xiang Zhang、Gian Filippo Ruda、Xiaoguang Chen、Dali Yin

  DOI：10.1039/c4cc06762b

  日期：——

  A new class of fluorophores 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) is developed and is suitable as reagents for biological imaging.

  一种新型荧光物质3-烷基-6-甲氧基-7-羟基-香豆素（AMHCs）已开发，并适用于生物成像试剂。
• Production of isoflavone derivatives
  申请人：Heaton Andrew

  公开号：US20050143588A1

  公开（公告）日：2005-06-30

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  描述了异黄酮氢化的方法，可以获得可操作数量的异黄烷-4-醇、异黄烯和异黄烷。在使用药用可接受的试剂和溶剂时，可以高纯度地获得异黄酮衍生物，并且产率接近定量。
• A mild and efficient protocol to synthesize chromones, isoflavones, and homoisoflavones using the complex 2,4,6-trichloro-1,3,5-triazine/dimethylformamide
  作者：G. Mahaboob Basha、S. Kumar Yadav、R. Srinuvasarao、S. Prasanthi、T. Ramu、N. Mangarao、V. Siddaiah

  DOI：10.1139/cjc-2013-0137

  日期：2013.8

  A mild and efficient one-flask method has been developed for the synthesis of chromones, isoflavones, and homoisoflavones from 2-hydroxyacetophenones, deoxybenzoins, and dihydrochalcones, respectively, via one-carbon extension using the complex 2,4,6-trichloro-1,3,5-triazine/dimethylformamide. Deoxybenzoins and dihydrochalcones were prepared in situ by the reaction of readily available substituted phenols with phenylacetic acids and 3-phenylpropanoic acids, respectively. This method allows the synthesis of a wide range of compounds with multiple phenolic hydroxyls and other substituents. The methodology has been applied to the synthesis of three naturally occurring isoflavones such as formononetin (9c), daidzein (9d), and retusin (9h).

  已开发出一种温和高效的一瓶法合成方法，用于从2-羟基苯乙酮、去氧苯甲酮和二氢黄酮分别通过一碳延伸使用复合物2,4,6-三氯-1,3,5-三嗪/二甲基甲酰胺合成香豆素、异黄酮和同异黄酮。去氧苯甲酮和二氢黄酮分别通过易得的取代苯酚与苯乙酸和3-苯基丙酸反应原位制备。该方法允许合成具有多个酚羟基和其他取代基的广泛化合物。该方法已应用于合成三种天然存在的异黄酮，如异黄酮（9c）、黄豆异黄酮（9d）和利图素（9h）。