2,6-dibromo-4-(4-nitrophenylsulfanyl)-pyridine | 231287-48-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,6-dibromo-4-(4-nitrophenylsulfanyl)-pyridine
• 英文别名: 2,6-dibromo-4-(4-nitrophenylsulphanyl)-pyridine；2,6-dibromo-4-(4-nitrophenyl)sulfanylpyridine
• CAS: 231287-48-2
• 化学式: C₁₁H₆Br₂N₂O₂S
• 分子量: 390.055
• InChiKey: AQZYJKWPVAMDSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-4-(4-nitrophenylsulfanyl)-pyridine 在 铁粉 、 氯化铵 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.5h， 生成 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulphonyl)-phenylamine
  参考文献：
  名称：

  Influence of the 5-HT₆ Receptor on Acetylcholine Release in the Cortex:  Pharmacological Characterization of 4-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine, a Potent and Selective 5-HT₆ Receptor Antagonist

  摘要：

  A small series of aryl pyridyl sulfones has been prepared and investigated for its 5-HT6 receptor binding properties. Thereof, pyrrolidinyl derivative 11 proved to be a very potent (pK(i) 9) and selective 5-HT6 receptor antagonist. By means of in vivo microdialysis in the frontal cortex and a passive avoidance paradigm, where 11 reversed a scopolamine induced retention deficit, a functional correlation between 5-HT6 receptors and cholinergic neurotransmission could be shown, supporting the therapeutic potential of 5-HT6 receptors in the treatment of cognitive deficits.

  DOI：

  10.1021/jm021085c
• 作为产物：
  描述：

  2,6-二溴-4-硝基吡啶氮氧化物 在 三溴化磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.0h， 生成 2,6-dibromo-4-(4-nitrophenylsulfanyl)-pyridine
  参考文献：
  名称：

  Influence of the 5-HT₆ Receptor on Acetylcholine Release in the Cortex:  Pharmacological Characterization of 4-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine, a Potent and Selective 5-HT₆ Receptor Antagonist

  摘要：

  A small series of aryl pyridyl sulfones has been prepared and investigated for its 5-HT6 receptor binding properties. Thereof, pyrrolidinyl derivative 11 proved to be a very potent (pK(i) 9) and selective 5-HT6 receptor antagonist. By means of in vivo microdialysis in the frontal cortex and a passive avoidance paradigm, where 11 reversed a scopolamine induced retention deficit, a functional correlation between 5-HT6 receptors and cholinergic neurotransmission could be shown, supporting the therapeutic potential of 5-HT6 receptors in the treatment of cognitive deficits.

  DOI：

  10.1021/jm021085c

文献信息

• Benzosulfone derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US05990105A1

  公开（公告）日：1999-11-23

  The present invention relates to novel compounds of the general formula ##STR1## wherein R.sup.1 is hydrogen; R.sup.2 is hydrogen, trifluoromethyl or lower alkyl; R.sup.3 is hydrogen or amino; or R.sup.1 and R.sup.2 or R.sup.3 and R.sup.2 taken together are --CH.dbd.CH--CH.dbd.CH--; Z is pyrimidin-4-yl, pyridin-4-yl, pyridin-2-yl or phenyl; R.sup.4, R.sup.5 are each independently hydrogen, lower alkyl, trifluoromethyl, halogen, lower alkoxy, nitrilo, amino, lower alkyl-amino, di-lower alkyl-amino, piperazinyl, morpholinyl, pyrrolidinyl, vinyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkenyl, t-buthylethinyl, hydroxyalkylethinyl, phenylethinyl, naphthyl, thiophenyl, or phenyl, which may be substituted by halogen, lower alkoxy, lower alkyl, trifluoromethyl or nitro, or a group --NH(CH.sub.2).sub.n NR.sup.6 R.sup.7, --N(CH.sub.3)(CH.sub.2).sub.n NR.sup.6 R.sup.7, --NH(CH.sub.2).sub.n -morpholin-4-yl or --NH(CH.sub.2).sub.n OH; n is 2-4 R.sup.6 and R.sup.7 are each independently hydrogen or lower alkyl, and to their pharmaceutically acceptable salts. It has been found that the compounds of formula I possess a selective affinity to 5HT-6 receptors.

  本发明涉及一般式为##STR1##的新化合物，其中R.sup.1为氢；R.sup.2为氢，三氟甲基或较低的烷基；R.sup.3为氢或氨基；或者R.sup.1和R.sup.2或R.sup.3和R.sup.2一起取--CH.dbd.CH--CH.dbd.CH--；Z为嘧啶-4-基，吡啶-4-基，吡啶-2-基或苯基；R.sup.4，R.sup.5各自独立地为氢，较低烷基，三氟甲基，卤素，较低烷氧基，氰基，氨基，较低烷基氨基，二较低烷基氨基，哌嗪基，吗啉基，吡咯烷基，乙烯基，C.sub.3 -C.sub.6环烷基，C.sub.3 -C.sub.6环烯基，叔丁基乙炔基，羟基烯基，苯基乙炔基，萘基，噻吩基或苯基，可以被卤素，较低烷氧基，较低烷基，三氟甲基或硝基取代，或者为--NH(CH.sub.2).sub.n NR.sup.6 R.sup.7，--N(CH.sub.3)(CH.sub.2).sub.n NR.sup.6 R.sup.7，--NH(CH.sub.2).sub.n -吗啉-4-基或--NH(CH.sub.2).sub.n OH的基团；n为2-4，R.sup.6和R.sup.7各自独立地为氢或较低烷基，以及它们的药用可接受盐。已发现，式I的化合物具有对5HT-6受体的选择性亲和力。
• US5990105A
  申请人：——

  公开号：US5990105A

  公开（公告）日：1999-11-23
• Influence of the 5-HT₆ Receptor on Acetylcholine Release in the Cortex:  Pharmacological Characterization of 4-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine, a Potent and Selective 5-HT₆ Receptor Antagonist
  作者：Claus Riemer、Edilio Borroni、Bernard Levet-Trafit、James R. Martin、Sonia Poli、Richard H. P. Porter、Michael Bös

  DOI：10.1021/jm021085c

  日期：2003.3.1

  A small series of aryl pyridyl sulfones has been prepared and investigated for its 5-HT6 receptor binding properties. Thereof, pyrrolidinyl derivative 11 proved to be a very potent (pK(i) 9) and selective 5-HT6 receptor antagonist. By means of in vivo microdialysis in the frontal cortex and a passive avoidance paradigm, where 11 reversed a scopolamine induced retention deficit, a functional correlation between 5-HT6 receptors and cholinergic neurotransmission could be shown, supporting the therapeutic potential of 5-HT6 receptors in the treatment of cognitive deficits.