(E)-3-(3,5-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one

• 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: (E)-3-(3,5-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one
• 英文别名: (E)-3-(3,5-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: RWOYCGABFPHNGL-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：

  (E)-3-(3,5-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以70%的产率得到2-(3,5-Dimethoxy-phenyl)-7-methoxy-chroman-4-one
  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：

  丹皮酚 、 3,5-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以85%的产率得到(E)-3-(3,5-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one
  参考文献：
  名称：

  1-（4-氨基磺酰基苯基）-3,5-二芳基吡唑啉衍生物的合成作为有效的抗炎和抗菌剂

  摘要：

  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。

  DOI：

  10.1007/s00044-011-9823-x

文献信息

• 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。
• 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.
• ——
  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.
• Optimization of Acryloylphenylcarboxamides as Inhibitors of ABCG2 and Comparison with Acryloylphenylcarboxylates
  作者：Stefanie Kraege、Katja Stefan、Sebastian C. Köhler、Michael Wiese

  DOI：10.1002/cmdc.201600455

  日期：2016.11.21

  a methoxy group that improved the inhibitory activity of chalcones would also be beneficial for the acryloylphenylcarboxamide scaffold. Indeed, this modification led to highly potent ABCG2 inhibitors. To support the hypothesis of a beneficial effect of the amide linker, six acryloylphenylcarboxylates were synthesized and investigated for their inhibitory activity. Replacement of the amide linker with

  ABCG2属于ATP结合盒（ABC）蛋白的超家族，并且由于其对肿瘤细胞的交叉耐药性（被称为多药耐药性（MDR））而与抗癌化学疗法的有限成功相关。已经开发了几种类型的ABCG2抑制剂来提高化学疗法的效力。合成了一系列与另外的芳族残基偶联的查耳酮，并研究了它们对ABC转运蛋白的抑制作用。在我们之前的工作中，我们确定链接器在A形环上的首选位置是邻位，并在额外的环上发现了几种取代方式，从而提高了效能。在这项研究中，我们调查了改善查尔酮的抑制活性的甲氧基是否也对丙烯酰基苯基羧酰胺支架有益。实际上，这种修饰导致了高效的ABCG2抑制剂。为了支持酰胺连接基的有益作用的假说，合成了六种丙烯酰基苯基羧酸盐，并研究了它们的抑制活性。用酯基取代酰胺连接基导致抑制作用降低。分子建模表明两个系列的构象偏好不同，从而解释了酰胺接头的积极作用。