(2E)-1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one | 76650-20-9

• 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: (2E)-1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one
• 英文别名: (E)-3-(3,4-dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one；3.4.2'.4'.6'-pentamethoxy-trans-chalcone；3.4.2'.4'.6'-Pentamethoxy-trans-chalkon；3,4,2',4',6'-Pentamethoxychalcone
• CAS: 76650-20-9
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: TVKGYMYAOVADOP-SOFGYWHQSA-N

物化性质

• 熔点：
  117.5 °C
• 沸点：
  538.8±50.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 2,4,6-三甲氧基苯乙酮 在 potassium hydroxide 作用下， 反应 0.08h， 以68%的产率得到(2E)-1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis of Xanthohumol Analogues and Discovery of Potent Thioredoxin Reductase Inhibitor as Potential Anticancer Agent

  摘要：

  The selenoprotein thioredoxin reductases (TrxRs) are attractive targets for anticancer drugs development. Xanthohumol (Xn), a naturally occurring polyphenol chalcone from hops, has received increasing attention because of its multiple pharmacological activities. We synthesized Xn and its 43 analogues and discovered that compound 13n displayed the highest cytotoxicity toward HeLa cells (IC50 = 1.4 mu M). Structure-activity relationship study indicates that the prenyl group is not necessary for cytotoxicity, and introducing electron-withdrawing group, especially on the meta-position, is favored. In addition, methylation of the phenoxyl groups generally improves the potency. Mechanistic study revealed that 13n selectively inhibits TrxR and induces reactive oxygen species and apoptosis in HeLa cells. Cells overexpressing TrxR are resistant to 13n insult, while knockdown of TrxR sensitizes cells to 13n treatment, highlighting the physiological significance of targeting TrxR by 13n. The clarification of the structural determinants for the potency would guide the design of novel potent molecules for future development.

  DOI：

  10.1021/jm5016507

文献信息

• Diarylalkanes as potent inhibitors of binuclear enzymes
  申请人：Jia Qi

  公开号：US20050267047A1

  公开（公告）日：2005-12-01

  The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.

  本发明实施了一种策略，将酶抑制测定与化学去重复过程相结合，以识别活性植物提取物和特定化合物——二芳基烷烃和/或二芳基醇，这些化合物特异性地抑制双核酶功能。本发明包括由一种或多种二芳基烷烃和/或二芳基醇组成的物质组合物，其抑制双核酶的活性，特别是酪氨酸酶，并防止黑色素过度产生。本发明还提供了一种抑制双核酶活性的方法，特别是酪氨酸酶，以及一种预防和治疗与双核酶功能相关的疾病和病况的方法。本发明还包括一种预防和治疗黑色素过度产生以及与之相关的皮肤疾病和病况的方法。预防和治疗与双核酶功能和黑色素过度产生相关的疾病和病况的方法包括向需要的宿主施用由一种或多种植物合成和/或分离的一种或多种二芳基烷烃和/或二芳基醇组成的组合物的有效量，以及药用载体。
• Method for the Synthesis of Aspalathin and Analogues Thereof
  申请人：Van der Westhuizen Jan Hendrik

  公开号：US20130018182A1

  公开（公告）日：2013-01-17

  A method of synthesising Aspalathin and its analogues or derivatives is disclosed. The method comprises synthesising a compound of formula 1 or its analogues or derivatives: wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is independently selected from the group consisting of —H, —OH, hydrocarbyl groups, saccharide moieties and —OR 15 ; R 15 is selected from the group consisting of hydrogen, a hydrocarbyl group (e.g. methoxy or ethoxy), an acyl group and a benzyl group; and R 11 , R 12 , R 13 and R 14 are independently selected from the group consisting of —H, hydrocarbyl groups, saccharide moieties, an acyl group and a benzyl group. The method comprises the step of coupling a sugar to a dihydrochalcone, chalcone or flavanone, or coupling the sugar to an intermediate for producing a dihydrochalcone, chalcone or flavanone followed by coupling of the sugar-intermediate adduct to a further intermediate for producing a dihydrochalcone, chalcone or flavanone, and transforming the product thereof into a compound of formula 1 or an analogue or derivative thereof.

  公开了一种合成Aspalathin及其类似物或衍生物的方法。该方法包括合成式1或其类似物或衍生物的化合物：其中R1、R2、R3、R4、R5、R6、R7、R8、R9和R10中的每一个都是独立选择自羟基、烃基、糖基团和—OR15的群组；R15选择自氢、烃基（例如甲氧基或乙氧基）、酰基和苄基；而R11、R12、R13和R14则独立选择自—H、烃基、糖基团、酰基和苄基的群组。该方法包括将糖与二氢黄烷酮、黄烷酮或黄酮偶联，或将糖与用于产生二氢黄烷酮、黄烷酮或黄酮的中间体偶联，然后将糖-中间体加合物偶联到用于产生二氢黄烷酮、黄烷酮或黄酮的进一步中间体上，并将其转化为式1或其类似物或衍生物的化合物。
• DIARYLALKANES AS POTENT INHIBITORS OF BINUCLEAR ENZYMES
  申请人：Unigen, Inc.

  公开号：US20140371491A1

  公开（公告）日：2014-12-18

  The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.

  本发明实施了一种策略，将酶抑制测定与化学去重过程相结合，以鉴定活性植物提取物及其中特定化合物——二芳基烷烃和/或二芳基烷醇，其特异性抑制双核酶功能。本发明包括由一种或多种二芳基烷烃和/或二芳基烷醇组成的物质组合物，其抑制双核酶的活性，特别是酪氨酸酶，从而防止黑色素过度产生。本发明还提供了一种抑制双核酶活性的方法，特别是酪氨酸酶，并提供了一种预防和治疗与双核酶功能相关的疾病和病症的方法。本发明还包括一种预防和治疗黑色素过度产生及其相关皮肤疾病和病症的方法。预防和治疗与双核酶功能和黑色素过度产生相关的疾病和病症的方法包括向需要的宿主施用一种由一种或多种从一种或多种植物中合成和/或分离出的二芳基烷烃和/或二芳基烷醇组成的组合物的有效量，以及药学上可接受的载体。
• 336. The chemistry of the “insoluble red” woods. Part III. The structure of santal and a note on orobol
  作者：Alexander Robertson、C. W. Suckling、W. B. Whalley

  DOI：10.1039/jr9490001571

  日期：——
• 1-(3-METHYL-2,4-DIMETHOXYPHENYL)-3-(2',4'-DIHYDROXYPHENYL)-PROPANE AS A POTENT TYROSINASE INHIBITOR
  申请人：Unigen, Inc.

  公开号：EP1748767B1

  公开（公告）日：2011-12-28