6-Bromobenzo[f][1,3]benzodioxole | 1235379-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-Bromobenzo[f][1,3]benzodioxole
• CAS: 1235379-17-5
• 化学式: C₁₁H₇BrO₂
• 分子量: 251.079
• InChiKey: DWCAINKRGDSQTI-UHFFFAOYSA-N

物化性质

• 沸点：
  356.9±11.0 °C(Predicted)
• 密度：
  1.663±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  naphtho[2,3-d][1,3]dioxole 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基苯并 、 copper(I) bromide 作用下， 以 甲醇 、 环己烷 、 水 为溶剂， 生成 6-Bromobenzo[f][1,3]benzodioxole
  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

文献信息

• 3,9-DIAZABICYCLO[3.3.1]NONANE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
  申请人：Peters Dan

  公开号：US20090036456A1

  公开（公告）日：2009-02-05

  This invention relates to novel 3,9-diazabicyclo[3.3.1]nonane derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.

  本发明涉及一种新型的3,9-二氮杂双环[3.3.1]壬烷衍生物，可用作单胺神经递质再摄取抑制剂。在其他方面，本发明涉及使用这些化合物进行治疗的方法，以及包含本发明化合物的制药组合物。
• NOVEL 3,9-DIAZABICYCLO[3.3.1]NONANE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
  申请人：PETERS Dan

  公开号：US20100160333A1

  公开（公告）日：2010-06-24

  3,9-diazabicyclo[3.3.1]nonane derivatives, useful as monoamine neurotransmitter re-uptake inhibitors. Also, use of these compounds in a method for therapy and in pharmaceutical compositions comprising the compounds. The 3,9-diazabicyclo[3.3.1]nonane derivatives have the formula wherein R a and R b are as described in the application. Also disclosed are stereoisomers and pharmaceutically acceptable salts of the compounds.

  3,9-二氮杂双环[3.3.1]壬烷衍生物，可用作单胺神经递质再摄取抑制剂。此外，本发明还涉及使用这些化合物进行治疗的方法以及包含这些化合物的制药组合物。3,9-二氮杂双环[3.3.1]壬烷衍生物的化学式如下，其中Ra和Rb如申请中所述。此外，还揭示了这些化合物的立体异构体和药用可接受盐。
• US7700596B2
  申请人：——

  公开号：US7700596B2

  公开（公告）日：2010-04-20
• US8071598B2
  申请人：——

  公开号：US8071598B2

  公开（公告）日：2011-12-06