2'-Hydroxy-2,3,4'-trimethoxychalcone | 109469-63-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2'-Hydroxy-2,3,4'-trimethoxychalcone
• 英文别名: (E)-1-(2′-hydroxy-4′-methoxyphenyl)-3-(2,3-dimethoxyphenyl)prop-2-en-1-one；(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,3-dimethoxyphenyl)prop-2-en-1-one；(E)-3-(2,3-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one；2'-hydroxy-2,3,4'-trimethoxy-trans-chalcone；2'-Hydroxy-2,3,4'-trimethoxy-trans-chalkon
• CAS: 109469-63-8
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: ZPBDKGAFNCLNTD-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-Hydroxy-2,3,4'-trimethoxychalcone 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以50%的产率得到7,2',3'-trimethoxyflavanone
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1014490817731
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 2,3-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以72%的产率得到2'-Hydroxy-2,3,4'-trimethoxychalcone
  参考文献：
  名称：

  糖基化黄酮醇文库的合成。

  摘要：

  黄酮醇是从植物中分离出来的一类重要的天然产物。一些糖基化的黄酮醇表现出非常有趣的生物学活性。通过Algar-Flynn-Oyamada反应，由2'-羟基苯乙酮和苯甲醛制得黄酮醇。这些黄酮醇与各种糖基供体的糖基化提供了糖基化黄酮醇的文库。这些化合物可能是有用的药理活性化合物，并将对其生物学活性进行研究。

  DOI：

  10.1016/j.tetlet.2008.10.032

文献信息

• Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents
  作者：Mopur Vijaya Bhaskar Reddy、Hsin-Yi Hung、Ping-Chung Kuo、Guan-Jhong Huang、Yu-Yi Chan、Shiow-Chyn Huang、Shwu-Jen Wu、Susan L. Morris-Natschke、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmcl.2017.02.038

  日期：2017.4

  Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in LPS-activated mouse peritoneal macrophages. Among the tested compounds, a 1,3-diarylpropane analog, 2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol

  通过醛醇缩合制备二十一个查耳酮，随后将这些化合物还原，得到相应的二氢查耳酮和1，3-二苯基丙烷衍生物。检查了合成产物对LPS活化的小鼠腹膜巨噬细胞中NO抑制的影响。在测试的化合物中，1,3-二芳基丙烷类似物2-（3-（3,4-二甲氧基苯基）丙基）-5-甲氧基苯酚（3p）对NO的产生表现出最显着的抑制作用。为了研究作用机理，通过免疫印迹研究了3p对iNOS和COX-2蛋白表达的影响。结果得出结论，3p能够通过ERK，p38和JNK减弱NF-κB信号传导而抑制LPS诱导的RAW264.7细胞中的iNOS表达。
• Synthesis of 1-(4-aminosulfonylphenyl)-3,5-diarylpyrazoline derivatives as potent antiinflammatory and antimicrobial agents
  作者：Pawan K. Sharma、Satish Kumar、Pawan Kumar、Pawan Kaushik、Chetan Sharma、Dhirender Kaushik、Kamal R. Aneja

  DOI：10.1007/s00044-011-9823-x

  日期：2012.10

  A new series of 1-(4-aminosulfonylphenyl)-3,5-diaryl pyrazolines (5) was synthesized by the reaction of appropriate chalcones 3 with 4-hydrazinobenzenesulfonamide hydrochloride (4) in ethanol in the presence of catalytic amount of acetic acid. All newly synthesized compounds were in vivo evaluated for their antiinflammatory activity using carrageenan-induced rat paw edema assay. Five of the newly synthesized

  在催化量的乙酸存在下，使合适的查尔酮3与4-肼基苯磺酰胺盐酸盐（4）在乙醇中反应，合成了一系列新的1-（4-氨基磺酰基苯基）-3,5-二芳基吡唑啉（5）。使用角叉菜胶诱导的大鼠爪水肿测定法在体内评估所有新合成的化合物的抗炎活性。新合成的5种化合物5d，5g，5h，5i和5m显示出显着的抗炎活性，角叉菜胶注射后3小时抑制作用大于55％。评价所有新合成的化合物对两种革兰氏阳性细菌（金黄色葡萄球菌和枯草芽孢杆菌）的体外抗菌活性；两种革兰氏阴性细菌（大肠杆菌和铜绿假单胞菌）和两种酵母菌（白色念珠菌和酿酒酵母）。一些新合成的化合物5a，5f，5g，5h，5j和5k对啤酒酵母显示出优异的抗真菌活性，比参考药物两性霉素B强。
• Prostaglandin reductase inhibitors
  申请人：Lin Rong-Hwa

  公开号：US20090124688A1

  公开（公告）日：2009-05-14

  A method of inhibiting 15-keto prostaglandin-Δ 13 -reductase 2 by contacting 15-keto prostaglandin-Δ 13 -reductase 2 with an aryl compound of Formula (I), (II), (III), or (IV) shown herein. Also disclosed are methods of treating peroxisome proliferators-activated receptor related diseases and lowering blood glucose levels by administering to a subject in need thereof an effective amount of such an aryl compound.

  本发明涉及一种通过将公式（I），（II），（III）或（IV）的芳基化合物与15-酮前列腺素-Δ13-还原酶2接触来抑制15-酮前列腺素-Δ13-还原酶2的方法。本发明还公开了通过向需要的受试者施用有效量的这种芳基化合物来治疗过氧化物酶体增殖物活化受体相关疾病和降低血糖水平的方法。
• Antimitotic and Antiproliferative Activities of Chalcones: Forward Structure–Activity Relationship
  作者：Ahcène Boumendjel、Julien Boccard、Pierre-Alain Carrupt、Edwige Nicolle、Madeleine Blanc、Annabelle Geze、Luc Choisnard、Denis Wouessidjewe、Eva-Laure Matera、Charles Dumontet

  DOI：10.1021/jm0708331

  日期：2008.4.1

  A series of 59 chalcones was prepared and evaluated for the antimitotic effect against K562 leukemia cells. The most active chalcones were evaluated for their antiproliferative activity against a panel of I I human and murine cell cancer lines. We found that three chalcones were of great interest as potential antimitotic drugs. In vivo safety studies conducted on one of the most active chalcones revealed that the compound was safe, allowing further in vivo antitumor evaluation.
• Arcoleo et al., Annali di Chimica, 1957, vol. 47, p. 75,80
  作者：Arcoleo et al.

  DOI：——

  日期：——