5,7-二甲氧基-2-甲基-4H-苯并吡喃-4-酮 | 26213-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 5,7-二甲氧基-2-甲基-4H-苯并吡喃-4-酮
• 英文名称: 2-methyl-5,7-dimethoxychromone
• 英文别名: 5,7-Dimethoxy-2-methyl-chromen-4-one；5,7-dimethoxy-2-methylchromen-4-one
• CAS: 26213-83-2
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: ARFUTALOPVWOBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  5,7-二甲氧基-2-甲基-4H-苯并吡喃-4-酮 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 5,7-Dimethoxy-2-(morpholin-4-ylmethyl)chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent

  摘要：

  A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-alpha and 70-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 mu M) while the compounds5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.071
• 作为产物：
  描述：

  1-(2-hydroxy-4, 6-dimethoxyphenyl)butane-1,3-dione 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.5h， 以50%的产率得到5,7-二甲氧基-2-甲基-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent

  摘要：

  A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-alpha and 70-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 mu M) while the compounds5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.071

文献信息

• [EN] NOVEL ARYL POTASSIUM CHANNEL BLOCKERS AND USES THEREOF<br/>[FR] NOUVEAUX INHIBITEURS DES CANAUX POTASSIQUES À GROUPE ARYLE ET LEURS UTILISATIONS
  申请人：BIONOMICS LTD

  公开号：WO2009043117A1

  公开（公告）日：2009-04-09

  The present invention relates to compounds useful in the modulation of potassium channel activity in cells, in particular the activity of Kv1.3 channels found in T cells. The invention also relates to the use of these compounds in the treatment or prevention of autoimmune and inflammatory diseases, including multiple sclerosis, pharmaceutical compositions containing these compounds and methods for their preparation.

  本发明涉及一种在细胞中调节钾通道活性的化合物，特别是用于T细胞中发现的Kv1.3通道的活性。该发明还涉及利用这些化合物治疗或预防自身免疫和炎症性疾病，包括多发性硬化症，含有这些化合物的药物组合物以及其制备方法。
• First intramolecular Diels–Alder reactions using chromone derivatives: synthesis of chromeno[3,4-<i>b</i>]xanthones and 2-(benzo[<i>c</i>]chromenyl)chromones
  作者：Hélio M. T. Albuquerque、Clementina M. M. Santos、José A. S. Cavaleiro、Artur M. S. Silva

  DOI：10.1039/c7nj05185a

  日期：——

  A series of novel (E)-2-(2-propargyloxystyryl)chromones and (E,E)-2-[4-(2-propargyloxyphenyl)buta-1,3-dien-1-yl]chromones were designed and synthesized via aldol condensation of 2-methylchromones with 2-propargyloxy(benzaldehyde and cinnamaldehyde), respectively. Both chromone derivatives were used as substrates in microwave-assisted intramolecular Diels–Alder reactions, affording chromeno[3,4-b]xanthones

  设计并合成了一系列新颖的（E）-2-（2-炔丙基氧基苯乙烯基）色酮和（E，E）-2- [4-（2-丙炔氧基苯基）丁-1,3-二烯-1-基]色酮通过2-甲基色酮与2-炔丙基氧基（苯甲醛和肉桂醛）的醛醇缩合反应。两种色酮衍生物均用作微波辅助的分子内Diels-Alder反应的底物，提供色酚[3,4- b ]氧杂蒽和2-（苯并[ c ]色烯基）色酮。这是第一个涉及分子内Diels-Alder反应中色酮衍生物用于合成新的氧杂环化合物的化合物，即氧杂蒽酮和黄酮类化合物。
• Yb(OTf)₃-Catalyzed Reactions of 5-Alkylidene Meldrum's Acids with Phenols:  One-Pot Assembly of 3,4-Dihydrocoumarins, 4-Chromanones, Coumarins, and Chromones
  作者：Eric Fillion、Aaron M. Dumas、Bryan A. Kuropatwa、Neil R. Malhotra、Tamsyn C. Sitler

  DOI：10.1021/jo052000t

  日期：2006.1.1

  Yb(OTf)3-catalyzed annulation reactions of phenols with 5-alkylidene Meldrum's acids enabled the synthesis of structurally diverse heterocycles in high isolated yields. A series of 4-substituted 3,4-dihydrocoumarins, 2,2-disubstituted 4-chromanones, coumarins, and 2-substituted chromones were readily and efficiently assembled, including the naturally occurring coumarins citropten, scoparone, and ayapin

  Yb（OTf）3催化的苯酚与5-亚烷基Meldrum酸的环化反应能够以高分离产率合成结构多样的杂环。一系列4-取代的3,4-二氢香豆素，2,2-二取代的4-发色酮，香豆素和2-取代的色酮容易而有效地组装，包括天然存在的香豆素香茅素，香柏酮和阿平。将苯酚添加到双亲电子性5-亚烷基Meldrum的酸中，通过两种不同的多键形成方式进行：弗里德-克拉夫特C-烷基化/ O-酰化和弗里德-克拉夫特C-酰化/ O-烷基化。催化环化反应的区域选择性由亚烷基部分上的取代度控制。
• NOVEL ARYL POTASSIUM CHANNEL BLOCKERS AND USES THEREOF
  申请人：Flynn Bernard Luke

  公开号：US20100297077A1

  公开（公告）日：2010-11-25

  The present invention relates to compounds useful in the modulation of potassium channel activity in cells, in particular the activity of Kv1.3 channels found in T cells. The invention also relates to the use of these compounds in the treatment or prevention of autoimmune and inflammatory diseases, including multiple sclerosis, pharmaceutical compositions containing these compounds and methods for their preparation.

  本发明涉及一种在细胞中调节钾通道活性的化合物，特别是Kv1.3通道在T细胞中的活性。本发明还涉及使用这些化合物治疗或预防自身免疫和炎症性疾病，包括多发性硬化症，含有这些化合物的制药组合物以及其制备方法。
• CHROMONE DERIVATIVE AND ALDOSE REDUCTASE INHIBITOR CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：TSUMURA & CO.

  公开号：EP0516860A1

  公开（公告）日：1992-12-09

  A chromone derivative represented by general formula (I) and an aldose reductase inhibitor containing the same as the active ingredient wherein R₁ and R₂ represent each lower alkyl, etc.; R₃ represents oxygen, sulfur, etc.; R₇ represents (un)substituted phenyl, etc.; and R₄ represents hydrogen or lower alkoxy. This compound is excellent in the inhibition of aldose reductase and is useful for treating various complications accompanying diabetes.

  一种由通式(I)代表的铬酮衍生物和一种以其为活性成分的醛糖还原酶抑制剂，其中 R₁ 和 R₂ 分别代表低级烷基等；R₃ 代表氧、硫等；R₇ 代表（未）取代的苯基等；R₄ 代表氢或低级烷氧基。这种化合物对醛糖还原酶有很好的抑制作用，可用于治疗糖尿病的各种并发症。