4-bromo-N,N-dipropylbenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-N,N-dipropylbenzamide
• 化学式: C₁₃H₁₈BrNO
• mdl: MFCD00448695
• 分子量: 284.196
• InChiKey: QOICZLJBFSFEIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-N,N-dipropylbenzamide 、 3.4-(亚甲基二氧基)苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 1.0h， 以75%的产率得到4-(benzo[d][1,3]dioxol-5-yl)-N,N-dipropylbenzamide
  参考文献：
  名称：

  Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives

  摘要：

  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.

  DOI：

  10.1021/jm5002277
• 作为产物：
  描述：

  三正丙胺 、 对溴苯乙腈 在 氧气 、 copper dichloride 作用下， 以 甲苯 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以91%的产率得到4-bromo-N,N-dipropylbenzamide
  参考文献：
  名称：

  铜催化的好氧氧化惰性碳？C和C ？N键断裂：合成叔酰胺的新策略

  摘要：

  惰性CC键与叔胺的铜催化需氧氧化酰胺化反应已开发出来，用于合成叔酰胺，叔酰胺是许多天然产物，药物和精细化学品中的重要单元。该方法在一键操作方案中结合了CC键激活，CN键断裂和CH键氧合，使用分子氧作为唯一的氧化剂而无任何其他配体。

  DOI：

  10.1002/chem.201403144

文献信息

• An efficient conversion of nitriles to amides: application in the synthesis of N,N-diethyl-m-toluamide (DEET™)
  作者：Apurba Bhattacharya、Robert Erik Plata、Victor Villarreal、Savitha Muramulla、Jiejun Wu

  DOI：10.1016/j.tetlet.2005.11.063

  日期：2006.1

  Arylnitriles react with magnesium amides to produce carboxamides in excellent yield. The method was applied for the preparation of the insect repellent DEET™.

  芳腈与酰胺化镁反应生成羧酰胺，产率极高。该方法用于制备驱蚊剂DEET™。
• 4-[ARYL(8-AZABICYCLO[3.2.1] OCTAN-3-YL)] AMINOBENZOIC ACID DERIVATIVES
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP1242421A1

  公开（公告）日：2002-09-25
• US6306876B1
  申请人：——

  公开号：US6306876B1

  公开（公告）日：2001-10-23
• [EN] 4-[ARYL(8-AZABICYCLO[3.2.1]OCTAN-3-YL)]AMINOBENZOIC ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDE AMINOBENZOIQUE 4-[ARYL(8-AZABICYCLO[3.2.1]OCTANE-3-YL)
  申请人：ORTHO MCNEIL PHARM INC

  公开号：WO2001046191A1

  公开（公告）日：2001-06-28

  4-[aryl(8-azabicyclo[3.2.1]octan-3yl)]aminobenzoic acid derivatives are delta-opioid receptor modulators. As delta-opioid receptor agonists, such compounds are useful as analgesics. Depending on their antagonist effect, such compounds may also be useful immunosuppressants, antiinflammatory agents, agents for the treatment of neurological and psychiatric conditions, medicaments for drug and alcohol abuse, agents for treating gastritis and diarrhea, cardiovascular agents and agents for the treatment of respiratory diseases.
• 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.