tert-butyl-4-(3,4-dichlorophenyl)piperidine-1-carboxylate | 153655-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl-4-(3,4-dichlorophenyl)piperidine-1-carboxylate
• 英文别名: tert-butyl 4-(3,4-dichlorophenyl)piperidine-1-carboxylate
• CAS: 153655-93-7
• 化学式: C₁₆H₂₁Cl₂NO₂
• 分子量: 330.254
• InChiKey: JWFRNEZXAIYQBO-UHFFFAOYSA-N

物化性质

• 沸点：
  409.0±45.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl-4-(3,4-dichlorophenyl)piperidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以91%的产率得到4-(3,4-二氯苯基)-哌啶盐酸盐
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4-phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

  摘要：

  New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Ca(v)3.1 (alpha(1G)) and Ca(v)3.2 (alpha(1H)) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of alpha(1G) and am subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.056
• 作为产物：
  描述：

  3,4-二氯溴苯 在 potassium phosphate 、 四(三苯基膦)钯 、 palladium on activated charcoal 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 36.0h， 生成 tert-butyl-4-(3,4-dichlorophenyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4-phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

  摘要：

  New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Ca(v)3.1 (alpha(1G)) and Ca(v)3.2 (alpha(1H)) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of alpha(1G) and am subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.056

文献信息

• Carbamoyl pyrrolidone derivatives for the treatment of depression and cerebnovascular disorders
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0580398A1

  公开（公告）日：1994-01-26

  A compound of the formula (I): wherein X¹ and X² each independently represents lower alkyl, lower alkoxy or halogen or a pharmaceutically acceptable salt thereof, which is useful as an active ingredient for a pharmaceutical composition for treating antidepressant or aftereffects of cerebrovascular impairments.

  式 (I) 的化合物： 其中 X¹ 和 X² 各自独立地代表低级烷基、低级烷氧基或卤素或其药学上可接受的盐，可用作治疗抗抑郁或脑血管损伤后遗症的药物组合物的活性成分。
• WO2008/59214
  申请人：——

  公开号：——

  公开（公告）日：——
• Carbamoyl pyrrolidone derivatives for the treatment of depression and cerebrovascular disorders
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0580398B1

  公开（公告）日：1999-11-24
• US5321035A
  申请人：——

  公开号：US5321035A

  公开（公告）日：1994-06-14
• [EN] BISAMLDE DERIVATIVES AND USE THEREOF AS FATTY ACID SYNTHASE INHIBITORS<br/>[FR] DÉRIVÉS DE BISAMIDE ET UTILISATION DE CEUX-CI EN TANT QU'INHIBITEURS DE L'ACIDE GRAS SYNTHASE
  申请人：ASTRAZENECA AB

  公开号：WO2008059214A1

  公开（公告）日：2008-05-22

  [EN] A compound of formula I, or a pharmaceutically acceptable salt thereof, processes for preparing such compounds, their use as Fatty Acid Synthase inhibitors, methods for their therapeutic use, particularly in the treatment of obesity and diabetes mellitus, and pharmaceutical compositions containing them.
  [FR] La présente invention a trait à un composé de formule I, ou à un sel, acceptable sur le plan pharmaceutique, de celui-ci, à des procédés de préparation desdits composés, à leur utilisation en tant qu'inhibiteurs de l'acide gras synthase, à des procédés d'utilisation thérapeutique de ceux-ci, en particulier dans le traitement de l'obésité et du diabète sucré, et à des compositions pharmaceutiques en contenant.