(E)-1,3-di(2,4,6-trimethoxyphenyl)-2-propen-1-one | 401504-46-9

• 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)-1,3-di(2,4,6-trimethoxyphenyl)-2-propen-1-one
• 英文别名: 2,2',4,4',6,6'-hexamethoxychalcone；(E)-2,2',4,4',6,6'-hexamethoxychalcone；(E)-1,3-bis(2,4,6-trimethoxyphenyl)prop-2-en-1-one
• CAS: 401504-46-9
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: WPEIVYGKGRTWQT-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-1,3-di(2,4,6-trimethoxyphenyl)-2-propen-1-one 、 肼甲酰亚胺酰胺一氯化氢 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以72%的产率得到5-(2,4,6-trimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride
  参考文献：
  名称：

  共轭胍hydr中的环链异构现象：实验和理论研究

  摘要：

  根据文献报道，在酸性条件下用氨基胍在较短的反应时间（1小时）内处理1,3-二芳基丙烯-2-酮可得到相应的胍。然而，当反应时间增加至12小时时，观察到环环状产物4，5-二氢-1 H-吡唑-1-羧酰亚胺酰胺的形成。这是共轭胍hydr中环链异构的第一种情况。无环共轭和相应的环状产物（4,5-二氢-1 H-吡唑-1-羧酰亚胺）可以通过紫外和核磁共振光谱清楚地区分。通过单晶XRD分析进一步证实了环异构体的形成。时间相关的11 H NMR研究表明开链化合物逐渐转变成环状化合物。使用量子化学方法探索了这两种产物形成的机理见解，结果表明环异构体在热力学上比开链异构体稳定6-11 kcal / mol，发现环化障碍为31.37 kcal /摩尔

  DOI：

  10.1016/j.tet.2018.04.042
• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 、 2,4,6-三甲氧基苯乙酮 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以62%的产率得到(E)-1,3-di(2,4,6-trimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Antimitotic and Antiproliferative Activities of Chalcones: Forward Structure–Activity Relationship

  摘要：

  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.

  DOI：

  10.1021/jm0708331

文献信息

• Synthesis, and Cyclization to Aurones and Flavones, of Alkoxy-Substituted Aryl, Arylalkynyl Ketones
  作者：Penelope J. Kerr、Simon M. Pyke、A. David Ward

  DOI：10.1071/ch07348

  日期：——

  corresponding aryl alkoxylarylalkynyl ketones in which one of the benzyl groups has been removed. Cyclization of these phenolic ketones using basic reagents (potassium carbonate in acetone is best) provides the corresponding aurone system. When the phenolic group of the alkynyl ketones is protected as the t-butyldimethylsilyl ether followed by cyclization, using 18-crown-6 and potassium fluoride, mixtures

  1,3,5-三苄氧基苯与烷氧基取代的苯丙酰氯的酰化提供相应的芳基烷氧基芳基炔基酮，其中一个苄基已被除去。使用碱性试剂（丙酮中的碳酸钾最好）环化这些酚酮提供相应的 aurone 系统。当炔基酮的酚基被保护为叔丁基二甲基甲硅烷基醚，然后使用 18-crown-6 和氟化钾进行环化时，产生相应的黄酮和黄酮的混合物。酮类形成的副产物是相应的 β-氯查耳酮，它也可以在碱性条件下环化为 aurone 产物。相似地，
• Novel Chalcone Derivatives With Antimitotic Activity
  申请人：Boumendjel Ahcene

  公开号：US20090182058A1

  公开（公告）日：2009-07-16

  The present invention relates to novel chalcone derivatives of formula (I): wherein X, Y, Z, W, RI, R2, R3, R4 and R5 are as defined, said derivatives having antimitotic activity, as well as to pharmaceutical compositions containing such compounds and to their use for making drugs.

  本发明涉及具有抗有丝分裂活性的新型葵花素衍生物的公式(I)：其中X、Y、Z、W、RI、R2、R3、R4和R5如定义所述，以及含有这种化合物的药物组合物，以及其用于制备药物的用途。
• DERIVES DE CHALCONE A ACTIVITE ANTIMITOTIQUE
  申请人：UNIVERSITE CLAUDE BERNARD - LYON 1

  公开号：EP1976818A2

  公开（公告）日：2008-10-08
• [EN] NOVEL CHALCONE DERIVATIVES WITH ANTIMITOTIC ACTIVITY<br/>[FR] NOUVEAUX DERIVES DE CHALCONE A ACTIVITE ANTIMITOTIQUE
  申请人：UNIV CLAUDE BERNARD LYON

  公开号：WO2007083060A2

  公开（公告）日：2007-07-26

  [EN] The present invention relates to novel chalcone derivatives of formula (I): in which X, Y, Z, W, R1, R2, R3, R4 and R5 are as defined, wherein said derivatives have antimitotic activity, and also to the pharmaceutical compositions containing such compounds and to the use thereof for the manufacture of medicaments.
  [FR] La présente invention concerne de nouveaux dérivés de chalcone de formule (I) : dans laquelle X, Y, Z, W, R1, R2, R3 R4 et R5 sont tels que définis, lesdits dérivés présentant une activité antimitotique, ainsi que les compositions pharmaceutiques contenant de tels composés et leur utilisation pour la fabrication de médicaments.
• 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.