1-(3-methoxy-4-methoxymethyloxyphenyl)-(1E)-1-buten-3-one | 52328-99-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(3-methoxy-4-methoxymethyloxyphenyl)-(1E)-1-buten-3-one
• 英文别名: (E)-4-[3-methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-one；1-(3-Methoxy-4-methoxymethoxyphenyl)but-1-en-3-on
• CAS: 52328-99-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: BTLPUHQSIJWSRG-SNAWJCMRSA-N

物化性质

• 沸点：
  384.4±37.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-methoxy-4-methoxymethyloxyphenyl)-(1E)-1-buten-3-one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以52%的产率得到4-(4-羟基-3-甲氧苯基)-3-丁烯-2-酮
  参考文献：
  名称：

  Synthesis of Natural and Non-natural Curcuminoids and Their Neuroprotective Activity against Glutamate-Induced Oxidative Stress in HT-22 Cells

  摘要：

  A strategy for the synthesis of natural and non-natural 5-deoxy-6,7-dihydrocurcuminoids (diarylheptanoids) was developed for the preparation of 14 compounds with varying aromatic substituent patterns and a different functionality in the aliphatic seven-carbon chain. The in vitro protective activity against glutamate-induced neuronal cell death was examined in the murine hippocampal cell line HT-22 to find structural motifs responsible for neuroprotective effects in vitro. Among the tested compounds the ferulic acid-like unit, present in the structures of (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-en-3-one (5) and (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-1-en-3-one (7), appeared to be an important feature for protection against glutamate-induced neurotoxicity. Both compounds demonstrated significant neuroprotective activity in a concentration range between 1 and 25 μM without showing toxic effects in a cytotoxicity assay with HT-22 cells. Furthermore, (E)-1,7-bis(3,4-dihydroxyphenyl)hept-1-en-3-one (9), exhibiting a caffeic acid-like structural motif, displayed a neuroprotective activity at a nontoxic concentration of 25 μM. In contrast, (1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione (4, di-O-demethylcurcumin) showed mainly cytotoxic effects. A corresponding single-ring analogue that contains the ferulic acid-like unit as an enone was not active.

  DOI：

  10.1021/np500396y
• 作为产物：
  描述：

  香草醛 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 1-(3-methoxy-4-methoxymethyloxyphenyl)-(1E)-1-buten-3-one
  参考文献：
  名称：

  Synthesis of Natural and Non-natural Curcuminoids and Their Neuroprotective Activity against Glutamate-Induced Oxidative Stress in HT-22 Cells

  摘要：

  A strategy for the synthesis of natural and non-natural 5-deoxy-6,7-dihydrocurcuminoids (diarylheptanoids) was developed for the preparation of 14 compounds with varying aromatic substituent patterns and a different functionality in the aliphatic seven-carbon chain. The in vitro protective activity against glutamate-induced neuronal cell death was examined in the murine hippocampal cell line HT-22 to find structural motifs responsible for neuroprotective effects in vitro. Among the tested compounds the ferulic acid-like unit, present in the structures of (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-en-3-one (5) and (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-1-en-3-one (7), appeared to be an important feature for protection against glutamate-induced neurotoxicity. Both compounds demonstrated significant neuroprotective activity in a concentration range between 1 and 25 μM without showing toxic effects in a cytotoxicity assay with HT-22 cells. Furthermore, (E)-1,7-bis(3,4-dihydroxyphenyl)hept-1-en-3-one (9), exhibiting a caffeic acid-like structural motif, displayed a neuroprotective activity at a nontoxic concentration of 25 μM. In contrast, (1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione (4, di-O-demethylcurcumin) showed mainly cytotoxic effects. A corresponding single-ring analogue that contains the ferulic acid-like unit as an enone was not active.

  DOI：

  10.1021/np500396y

文献信息

• [EN] NOVEL SMALL MOLECULES THAT BIND AND/OR MODULATE DIFFERENTFORMS OF TAU OLIGOMERS<br/>[FR] NOUVELLES PETITES MOLÉCULES QUI FIXENT ET/OU MODULENT DIFFÉRENTES FORMES D'OLIGOMÈRES TAU
  申请人：UNIV TEXAS

  公开号：WO2020219714A1

  公开（公告）日：2020-10-29

  The present invention relates to novel small molecules of Formulas I, II, III, Ilia, Illb, and IV and pharmaceutically acceptable salts thereof, as well as the preparation and the use thereof.

  本发明涉及新型小分子的化学式I、II、III、IIia、IIib和IV，以及其药用盐，以及其制备和使用。
• Cancer treatment using curcumin derivatives
  申请人：Vander Jagt L. David

  公开号：US20060276536A1

  公开（公告）日：2006-12-07

  Cancer or a precancerous condition is treated by administering a curcumin derivative to a subject.

  癌症或癌前病变可以通过向受试者施用姜黄素衍生物来治疗。
• Therapeutic curcumin derivatives
  申请人：Vander Jagt L. David

  公开号：US20070060644A1

  公开（公告）日：2007-03-15

  Curcumin analogues and methods are provided for treatment of disease.

  提供了类姜黄素和治疗疾病的方法。
• THERAPEUTIC CURCUMIN DERIVATIVES
  申请人：STC.UNM

  公开号：US20150011494A1

  公开（公告）日：2015-01-08

  Curcumin analogues and methods are provided for treatment of disease.

  提供了类姜黄素及其方法，用于治疗疾病。
• Anti-oxidative and anti-inflammatory curcumin-related phenolics from rhizomes of Curcuma domestica
  作者：Toshiya Masuda、Akiko Jitoe、Junko Isobe、Nobuji Nakatani、Sigetomo Yonemori

  DOI：10.1016/0031-9422(93)85179-u

  日期：——

  Two new natural phenolics were isolated from the rhizomes of Curcuma domestica along with four known curcuminoids. The structures of the former were determined to be 1,5-bis(4-hydroxy-3-methoxyphenyl)-penta-(1E,4E)-1,4-dien-3-one and 1-(4-hydroxy-3-methoxyphenyl)-5-(-4-hydroxyphenyl)-penta-(1E,4E)-1,4-dien-3-one, respectively, by spectral data and syntheses. Anti-oxidant activity of the phenolics was determined by the inhibition of autoxidation of linoleic acid in a water-alcohol system. Anti-inflammatory activity of the isolated compounds was determined on mouse cars by using a tumour promoter, TPA (12-O-tetradecanoylphorbol-13-acetate) as an inducer.