(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide | 1313740-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide
• 英文别名: SCT-64；N-Piperoyl-N,N-dipropylamine；(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropylpenta-2,4-dienamide
• CAS: 1313740-79-2
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: BKOZTEJUHNEVPU-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二正丙胺 、 胡椒碱 在 三甲基氯硅烷 、 1,10-菲罗啉 、 六氯化钨 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 36.0h， 以48%的产率得到(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide
  参考文献：
  名称：

  钨催化的叔烷基酰胺的转酰胺

  摘要：

  转酰胺最近已成为使酰胺多样化的一种简单方便的方法。然而，臭名昭著的、完全烷基取代的叔酰胺的动力学和热力学要求的转酰胺化仍然是一个长期的挑战。在这里，我们描述了一种使用简单的氯化钨 (VI) 作为催化剂和三甲基氯硅烷作为添加剂来活化叔烷基酰胺以简化转酰胺化的方法。高度亲电和亲氧的钨催化剂能够选择性地切断叔烷基酰胺的 C-N 键，从而实现无数结构和电子不同的叔烷基酰胺和胺的转酰胺化。

  DOI：

  10.1021/acscatal.1c01840

文献信息

• Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives
  作者：Angela Schöffmann、Laurin Wimmer、Daria Goldmann、Sophia Khom、Juliane Hintersteiner、Igor Baburin、Thomas Schwarz、Michael Hintersteininger、Peter Pakfeifer、Mouhssin Oufir、Matthias Hamburger、Thomas Erker、Gerhard F. Ecker、Marko D. Mihovilovic、Steffen Hering

  DOI：10.1021/jm5002277

  日期：2014.7.10

  Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates gamma-aminobutyric acid type A receptors (GABA(A)R). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABA(A)R by means of a two-microelectrode voltage-clamp technique. GABA(A)R were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABA(A)R. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABA(A) (maximal GABA-induced chloride current modulation (IGABA-max = 1673% +/- 146%, EC50 = 51.7 +/- 9.5 mu M), while 25 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC50 = 13.8 +/- 1.8 mu M, IGABA-max = 760% +/- 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA(A)R modulators.
• Verfahren zur Herstellung von Piperonylidencrotonsäureamiden
  申请人：HAARMANN & REIMER GMBH

  公开号：EP0002735B1

  公开（公告）日：1980-12-10
• NOVEL PIPERINE DERIVATIVES AS GABA-A RECEPTORS MODULATORS
  申请人：Universität Wien

  公开号：EP2519511B1

  公开（公告）日：2015-12-16
• Modulators of Aldehyde Dehydrogenase and Methods of Use Thereof
  申请人：Mochly-Rosen Daria

  公开号：US20100113423A1

  公开（公告）日：2010-05-06

  The present disclosure provides compounds that function as modulators of aldehyde dehydrogenase (ALDH) enzymatic activity, as well as compositions and formulations comprising the compounds. The present disclosure provides therapeutic methods involving administering a subject compound, or a subject pharmaceutical composition.
• US20140343045A1
  申请人：——

  公开号：US20140343045A1

  公开（公告）日：2014-11-20