2-(4-羟基苯基)-7-甲氧基-2,3-二氢色烯-4-酮 | 32274-71-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(4-羟基苯基)-7-甲氧基-2,3-二氢色烯-4-酮
• 英文名称: 7-Methylliquiritigenin
• 英文别名: 2-(4-hydroxyphenyl)-7-methoxychroman-4-one；4’-hydroxy-7-methoxy-flavanone；4'-hydroxy-7-methoxyflavanone；(+/-)-2-(4-hydroxy-phenyl)-7-methoxy-chroman-4-one；(+/-)-2-(4-Hydroxy-phenyl)-7-methoxy-chroman-4-on；2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
• CAS: 32274-71-8
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: OJOSVTQXBSSCMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  494.1±45.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2-(4-羟基苯基)-7-甲氧基-2,3-二氢色烯-4-酮 在 甲醇 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 甲苯 、 silver(l) oxide 、 苯 作用下， 生成 (R)-2-(4-hydroxy-phenyl)-7-methoxy-chroman-4-one
  参考文献：
  名称：

  Tatsuda, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1946, vol. 67, p. 119,125

  摘要：

  DOI：
• 作为产物：
  描述：

  4-碘乙酰基苯酚 在 palladium diacetate 、 sodium methylate 、 三乙胺 、 三苯基膦 、 乙硫醇钠 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.0h， 生成 2-(4-羟基苯基)-7-甲氧基-2,3-二氢色烯-4-酮
  参考文献：
  名称：

  A new synthesis of flavonoids via Heck reaction

  摘要：

  Several naturally occurring flavonoids have been synthesised following a new proposed method based on the use of the Heck reaction. The key step involves the coupling of an aryl vinyl ketone with an aryl iodide. This procedure affords the flavonoid moiety in a single step. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.060

文献信息

• Structural Requirements of Flavonoids and Related Compounds for Aldose Reductase Inhibitory Activity.
  作者：Hisashi Matsuda、Toshio Morikawa、Iwao Toguchida、Masayuki Yoshikawa

  DOI：10.1248/cpb.50.788

  日期：——

  The methanolic extracts of several natural medicines and medicinal foodstuffs were found to show an inhibitory effect on rat lens aldose reductase. In most cases, flavonoids were isolated as the active constituents by bioassay-guided separation, and among them, quercitrin (IC50=0.15 μM), guaijaverin (0.18 μM), and desmanthin-1 (0.082 μM) exhibited potent inhibitory activity. Desmanthin-1 showed the most potent activity, which was equivalent to that of a commercial synthetic aldose reductase inhibitor, epalrestat (0.072 μM). In order to clarify the structural requirements of flavonoids for aldose reductase inhibitory activity, various flavonoids and related compounds were examined. The results suggested the following structural requirements of flavonoid: 1) the flavones and flavonols having the 7-hydroxyl and/or catechol moiety at the B ring (the 3′,4′-dihydroxyl moiety) exhibit the strong activity; 2) the 5-hydroxyl moiety does not affect the activity; 3) the 3-hydroxyl and 7-O-glucosyl moieties reduce the activity; 4) the 2–3 double bond enhances the activity; 5) the flavones and flavonols having the catechol moiety at the B ring exhibit stronger activity than those having the pyrogallol moiety (the 3′,4′,5′-trihydroxyl moiety).

  发现，几种天然药材和药用食品的甲醇提取物对大鼠晶状体醛糖还原酶显示抑制作用。在大多数情况下，通过生物测定指导的分离方法，分离得到黄酮类化合物作为活性成分，其中，槲皮苷（IC50=0.15 μM）、愈创木脂苷（0.18 μM）和去甲基芸香糖苷-1（0.082 μM）显示出强的抑制活性。去甲基芸香糖苷-1显示了最强的活性，相当于商品化合成醛糖还原酶抑制剂依帕司他（0.072 μM）的活性。为了阐明黄酮类化合物对醛糖还原酶抑制活性的结构要求，检测了各种黄酮类化合物及相关化合物。结果表明，黄酮类化合物的以下结构要求是：1）具有7-羟基和/或邻苯二酚结构的黄酮和黄酮醇（在B环上的3′,4′-二羟基结构）显示出强的活性；2）5-羟基结构并不影响活性；3）3-羟基和7-O-葡糖基结构降低活性；4）2-3双键增强活性；5）具有邻苯二酚结构的黄酮和黄酮醇显示出比具有连苯三酚结构（3′,4′,5′-三羟基结构）的化合物更强的活性。
• Design, Synthesis, and Structure-Activity Relationships of Bavachinin Analogues as Peroxisome Proliferator-Activated Receptor γ Agonists
  作者：Guoxin Du、Yuanyuan Zhao、Li Feng、Zhuo Yang、Jiye Shi、Cheng Huang、Bo Li、Fujiang Guo、Weiliang Zhu、Yiming Li

  DOI：10.1002/cmdc.201600554

  日期：2017.1.20

  receptor γ (PPARγ) agonists have been used for the treatment of diabetes with the effect of lowering blood glucose levels and improving insulin sensitivity. Natural compounds such as flavones, flavanones, and isoflavones have shown excellent PPARγ agonist activity. In this study, analogues of bavachinin were designed, synthesized, and evaluated by reporter gene assays for PPARγ agonist activity. Preliminary

  过氧化物酶体增殖物激活受体 γ (PPARγ) 激动剂已被用于治疗糖尿病，具有降低血糖水平和改善胰岛素敏感性的作用。黄酮、黄烷酮和异黄酮等天然化合物已显示出优异的 PPARγ 激动剂活性。在这项研究中，设计、合成了巴伐奇宁类似物，并通过报告基因分析评估了 PPARγ 激动剂的活性。总结了这些巴伐奇宁类似物的初步构效关系，发现七种化合物比母体黄烷酮巴伐奇宁具有更高的 PPARγ 激动剂活性。
• Rapid synthesis of 4-benzylidene and 4-[bis-(4-methoxyphenyl)-methylene-2-substituted phenyl-benzopyrans as potential selective estrogen receptor modulators (SERMs) using McMurry coupling reaction
  作者：Atul Gupta、Anila Dwivedy、Govind Keshri、Ramesh Sharma、Anil Kumar Balapure、Man Mohan Singh、Suprabhat Ray

  DOI：10.1016/j.bmcl.2006.08.126

  日期：2006.12

  alkylamino residues, designed as estrogen receptor (ER) binding ligands, were successfully synthesized through the McMurry coupling reaction of substituted benzaldehyde/substituted benzophenones and 2-hydroxyphenyl-7-methoxy-chroman-4-one in presence of lithium aluminum hydride and titanium (IV) chloride (LAH-TiCl(4)). Self-coupling of carbonyl reactants led to the formation of several side products. The

  设计成雌激素受体的7-甲氧基-4-（4-甲氧基亚苄基）-2-取代的苯基-苯并吡喃I和4- [双-（4-甲氧基苯基）-亚甲基-2-取代的苯基-苯并吡喃II，带有不同的烷基氨基残基，被设计为雌激素受体（ ER）的结合配体是在氢化铝锂和氯化钛（IV）（LAH-TiCl（ 4））。羰基反应物的自偶联导致形成几种副产物。评价原型的相对结合亲和力（RBA），以及它们的雌激素和抗雌激素活性。用化合物3、7a，7b，7c，8和10a观察到高水平的雌激素活性（> 50％增幅），以及它们的部分雌激素拮抗活性（> 或在子宫水平上为15％）表示化合物的成功设计。化合物4、7a，7b，7c和10a还具有显着的抗人腺癌细胞系（MCF-7细胞系）抗癌活性，这可能与其雌激素依赖性作用有关。
• ——
  作者：Christelle Pouget、Catherine Fagnere、Jean‐Philippe Basly、Anne‐Elise Besson、Yves Champavier、Gerard Habrioux、Albert‐Jose Chulia

  DOI：10.1023/a:1014490817731

  日期：——

  Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors: therefore. in an effort to develop novel anti breast cancer agents. B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern.Methods. A series of flavanones was prepared by cyclisation of 2'-hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity or these compounds was investigated using human placental microsomes and radiolabeled [1.2,6,7-H-3]-androstenedione as substrate.Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring subtitution pattern. Hydroxylation at position 3' and/or 4' enhanced the anti-aromatase activity thus, 3'.4'-dihydroxy-7-methoxyflavanone was found to he twice more potent than aminoglutethimide. the first aromatase inhibitor clinically used.Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these Compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.
• Mahal et al., Journal of the Chemical Society, 1935, p. 866
  作者：Mahal et al.

  DOI：——

  日期：——