1-(2-丁氧基苯基)哌嗪 | 106476-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(2-丁氧基苯基)哌嗪
• 英文名称: 1-(o-butoxyphenyl)piperazine
• 英文别名: 1-(2-butoxy-phenyl)-piperazine；1-o-butoxyphenylpiperazine；1-(o-Butoxyphenyl)piperazin；1-(2-Butoxyphenyl)piperazine
• CAS: 106476-37-3
• 化学式: C₁₄H₂₂N₂O
• mdl: MFCD16498457
• 分子量: 234.341
• InChiKey: YNPHKRWUIFAKLL-UHFFFAOYSA-N

物化性质

• 沸点：
  372.1±27.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-丁氧基苯基)哌嗪 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 41.0h， 生成 N-(1-azabicyclo[2.2.2]octan-3-yl)-2-[[4-(2-butoxyphenyl)piperazin-1-yl]methyl]-1H-benzimidazole-4-carboxamide
  参考文献：
  名称：

  苯并咪唑衍生物。第5部分：设计和合成新的苯并咪唑-芳基哌嗪衍生物，用作混合的5-HT1A / 5-HT3配体。

  摘要：

  通过在一般结构III中结合5-HT（1A）和5-HT（3）受体的药效学元素，设计了一系列新的混合苯并咪唑-芳基哌嗪衍生物。合成了化合物1-11，并评估了它们在两个5-羟色胺能受体上的结合亲和力，它们均显示出较高的5-HT（3）R亲和力（K（i）= 10-62nM），以及在化合物中具有邻烷氧基的衍生物芳基哌嗪环显示对5-HT（1A）R的纳摩尔亲和力（K（i）= 18-150nM）。此外，所有合成的化合物对α（1）-肾上腺素和多巴胺D（2）受体具有选择性（K（i）> 1000-10,000nM）。由于化合物3作为混合的5-HT（1A）/ 5-HT（3）配体对两个受体都具有高亲和力（5-HT（1A）：K（i）= 18.0 nM，5-HT（3）：K（i）＝ 27.2nM）。体外和体内发现表明，该化合物在5-HT（1A）Rs和5-HT（3）R拮抗剂中起部分激动剂的作用。这种新颖的混合5-HT（1A）/

  DOI：

  10.1016/j.bmc.2004.07.023
• 作为产物：
  描述：

  1-丁氧基-2-硝基苯 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 生成 1-(2-丁氧基苯基)哌嗪
  参考文献：
  名称：

  Activity of aromatic substituted phenylpiperazines lacking affinity for dopamine binding sites in a preclinical test of antipsychotic efficacy

  摘要：

  Generally, antipsychotic agents are dopamine receptor blocking agents that also block conditioned avoidance responding (CAR) in the rat. Recently, however, both (Q-methoxyphenyl)piperazine (OMPP, 1h) and (m-chlorophenyl)piperazine (MCPP, 1o) have been reported to block conditioned avoidance responding in the rat although neither has dopamine receptor blocking properties. The present paper examines the behavioral and biochemical profile of a number of additional substituted phenylpiperazines. None of the phenylpiperazines tested demonstrated high affinity for either dopamine D-1 or D-2 receptor sites, yet many were effective in blocking CAR. The results suggest that the phenylpiperazines may be effective antipsychotic agents without blocking dopamine receptors. Moreover, the active compounds did demonstrate activity in displacing ligand binding to serotonin receptors. Receptor binding profiles were determined for 5-HT-1A and 5-HT-1B binding sites as well as for 5-HT-2 sites. The data from this preclinical test suggest these phenylpiperazines might be effective antipsychotic agents acting via a nondopaminergic mechanism of action.

  DOI：

  10.1021/jm00125a020

文献信息

• 4-methyl-5-(2-(4-phenylpiperazin-1-yl)ethyl)thiazole derivatives their
  申请人：Institut de Recherches Chimiques et Biologiques Appliquees

  公开号：US05120736A1

  公开（公告）日：1992-06-09

  The present invention relates to novel 4-methyl-5-[2-(4-phenylpiperazin-1-yl)ethyl]thiazole derivatives of the general formula ##STR1## in which R is selected from a hydrogen atom, an alkyl radical having from 2 to 7 carbon atoms and an aralkyl radical of which the aryl moiety preferably consists of phenyl and of which the alkyl moiety has from 1 to 4 carbon atoms, and to the pharmaceutically acceptable salts of these derivatives. It further relates to a method of preparing these products and to pharmaceutical compositions in which they are incorporated. These derivatives are applied especially in the preparation of drugs intended for the treatment of functional dysuria associated with hyperactivity of the .alpha.-adrenergic sympathetic nervous system.

  本发明涉及一种新颖的通式为的4-甲基-5-[2-(4-苯基哌嗪-1-基)乙基]噻唑衍生物，其中R从氢原子、具有2至7个碳原子的烷基基团和芳基烷基基团中选择，其中芳基部分首选为苯基，烷基部分具有1至4个碳原子，并且这些衍生物的药学上可接受的盐。它还涉及制备这些产品的方法以及这些产品被纳入的药物组合物。这些衍生物特别适用于制备用于治疗与α-肾上腺素能交感神经系统过度活跃相关的功能性排尿障碍的药物。
• Design and synthesis of new benzimidazole-arylpiperazine derivatives acting as mixed 5-HT1A/5-HT3 ligands
  作者：Marı́a L. López-Rodrı́guez、Bellinda Benhamú、Mª José Morcillo、Ignacio Tejada、David Avila、Isabel Marco、Lucio Schiapparelli、Diana Frechilla、Joaquı́n Del Rı́o

  DOI：10.1016/s0960-894x(03)00706-6

  日期：2003.10

  A series of new benzimidazole-arylpiperazine derivatives III were designed, synthesized and evaluated for binding affinity at serotoninergic 5-HT(1A) and 5-HT(3) receptors. Compound IIIc was identified as a novel mixed 5-HT(1A)/5-HT(3) ligand with high affinity for both serotonin receptors and excellent selectivity over alpha(1)-adrenergic and dopamine D(2) receptors. This compound was characterized

  设计，合成和评估了一系列新的苯并咪唑-芳基哌嗪衍生物III，对5-羟色胺能5-HT（1A）和5-HT（3）受体的结合亲和力。化合物IIIc被确定为一种新型的混合5-HT（1A）/ 5-HT（3）配体，对5-羟色胺受体具有很高的亲和力，并且对α（1）-肾上腺素和多巴胺D（2）受体具有优异的选择性。该化合物被表征为在5-HT（1A）Rs和5-HT（3）R拮抗剂的部分激动剂，并且在被动回避学习测试中有效预防毒蕈碱受体阻滞诱导的认知缺陷。
• Pyrrole Mannich bases as potential antipsychotic agents
  作者：Malcolm K. Scott、Gregory E. Martin、Deena L. DiStefano、Cynthia L. Fedde、Michael J. Kukla、Donna L. Barrett、William J. Baldy、Robert J. Elgin、James M. Kesslick

  DOI：10.1021/jm00081a018

  日期：1992.2

  receptors, they are reasonably potent in inhibiting conditioned avoidance responding (CAR) in the rat, an indication of potential antipsychotic activity. Conversion of these arylpiperazines to pyrrole Mannich bases has provided a series of compounds (10-44) which exhibit potent inhibition of CAR when given po and have strong affinity for both the D-2 and 5-HT-1A binding sites. Some of these agents also

  最近，我们报道了一系列芳基哌嗪4，它们对5-羟色胺5-HT-1A和5-HT-1B结合位点表现出高亲和力。尽管这些化合物与多巴胺D-1和D-2受体的相互作用较弱，但它们在抑制大鼠的条件回避反应（CAR）方面具有相当强的效力，这是潜在抗精神病药活性的指标。这些芳基哌嗪向吡咯曼尼希碱的转化提供了一系列化合物（10-44），当给予po时，它们显示出对CAR的有效抑制，并且对D-2和5-HT-1A结合位点都具有强亲和力。这些试剂中的一些也不能产生僵直症。
• Optically active antifungal azoles: synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol
  作者：Ram Shankar Upadhayaya、Neelima Sinha、Sanjay Jain、Nawal Kishore、Ramesh Chandra、Sudershan K. Arora

  DOI：10.1016/j.bmc.2004.02.014

  日期：2004.5

  A series of (2 R, 3S)-2-(2,4-difluorophenyl)-3-(5-2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazo-2-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (11a-n) and (2R,3S)-2-(2,4-difluorophenyl)-3-(5-2-[4-aryl-piperazin-1-yi]-ethyl}-tetrazole-1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (12a-n) has been synthesized. The antifungal activity of compounds was evaluated by in vitro agar diffusion and broth dilution assay. Compounds 11d and its positional isomer 12d having 3-trifluoromethyl substitution on the phenyl ring of piperazine demonstrated significant antifungal activity against variety of fungal cultures (Candida spp. C. neoformans and Aspergillus spp.). The compound 12d showed MIC value of 0.12mug/mL for C. albicans, C albicans V-01-191A-261 (resistant strain); 0.25mug/mL for C tropicalis, C parapsilosis ATCC 22019 and C krusei and MIC value of 0.5 mug/mL for C glabrata, C krusei ATCC 6258, which is comparable to itraconazole and better than fluconazole. Further, compound 11d showed significant activity (MIC; 0.25-0.5 mug/mL) against Candida spp. and strong anticryptococcal activity (MIC; 0.25 mug/mL) against C neoformans. (C) 2004 Elsevier Ltd. All rights reserved.
• Urbain; Schumer; Gubin, European Journal of Medicinal Chemistry, 1982, vol. 17, # 4, p. 359 - 364
  作者：Urbain、Schumer、Gubin、Descamps

  DOI：——

  日期：——