3-(4-(4-fluorophenyl)piperazin-1-yl)propan-1-ol | 105173-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(4-(4-fluorophenyl)piperazin-1-yl)propan-1-ol
• 英文别名: 3-[4-(4-fluoro-phenyl)-1-piperazinyl]propanol；1-Piperazinepropanol, 4-(4-fluorophenyl)-；3-[4-(4-fluorophenyl)piperazin-1-yl]propan-1-ol
• CAS: 105173-87-3
• 化学式: C₁₃H₁₉FN₂O
• mdl: MFCD11613837
• 分子量: 238.305
• InChiKey: CQGQIENALOHUTE-UHFFFAOYSA-N

物化性质

• 沸点：
  382.3±42.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-(4-fluorophenyl)piperazin-1-yl)propan-1-ol 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 16.0h， 生成 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine
  参考文献：
  名称：

  3- [2- [4-(4-Fluorobenzoyl)piperidin- 1-yl]ethyl] -5,6,7,8-tetrahydro-4(3H)-quinazolinones: serotonin 5-HT2A receptor antagonists endowed with potent central action

  摘要：

  A series of 5,6,7,8-tetrahydro-4(3H)-quinazolinones substituted at the 3-position with 4-benzoyl-1-ethylpiperidine, 4-(4-fluorobenzoyl)-1-ethylpiperidine, 4-[bis-(4-fluorophenyl)methylene]-1-ethylpiperidine, or 4-(4-fluorophenyl)-1-propylpiperazine have been prepared and evaluated in binding assays to determine their affinity at serotonin 5-HT2A receptors as well as in a functional test, ie, wet dog shakes (WDS) induced by L-5-hydroxytryptophan (L-5-HTP), a behavioural response which is mediated by stimulation of 5-HT receptors. Among the compounds prepared. 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-5,6,7,8-tetrahydro-4(3H)-quinazolinone (10b) and 2-methyl-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-5,6,7,8-tetrahydro-4(3H)-quinazolinone (10b) proved to be the most potent 5-HT,, receptor antagonists. In binding assays, the two compounds displayed similar affinity for 5-HT, receptors in the nanomolar range to ketanserin and ritanserin. In the WDS test, they were even more potent than ketanserin and ritanserin. Compound 10b, which was found to possess the highest potency and duration of action in the WDS test, was chosen for a preliminary evaluation of its ability to inhibit ethanol intake in rats, a response linked to blockade of the central 5-HT2A, receptors. This compound significantly reduced ethanol intake in rats from the first day of treatment. The results of the present study indicate that 10b is a potent centrally acting antagonist at 5-HT2A receptors.

  DOI：

  10.1016/s0223-5234(97)83291-6
• 作为产物：
  描述：

  1-(4-氟苯基)哌嗪 、 3-溴-1-丙醇 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到3-(4-(4-fluorophenyl)piperazin-1-yl)propan-1-ol
  参考文献：
  名称：

  Utility of azetidinium methanesulfonates for radiosynthesis of 3-[18F]fluoropropyl amines

  摘要：

  观察到 3-甲磺酰氧基丙基叔胺环化形成甲磺酸氮杂环丁烷。利用 3-甲磺酰氧基丙胺的热诱导环化反应制备了氮杂环丁烷甲磺酸盐。研究发现，氮杂环丁烷甲烷磺酸盐能有效地结合放射性[18F]氟化物（衰变校正产率大于 60%），从而高效合成了 3-[18F]fluoropropyl tertiary amines（3-[18F]氟丙基叔胺）。Copyright © 2004 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.884

文献信息

• Piperazinyl derivatives and methods of treating central nervous system
  申请人：Novo Nordisk A/S

  公开号：US05246935A1

  公开（公告）日：1993-09-21

  Piperazinyl derivatives of the general formula I ##STR1## wherein R.sup.1 represents substituted phenyl, 1- or 2-diazanaphthyl, azadiazanaphtyl or diazanaphtyl groups; n is 1, 2, 3 or 4; X is --O-- or ##STR2## wherein R.sup.2 is hydrogen, C.sub.1-6 -alkyl or C.sub.3-8 -cycloalkyl; Y is .dbd.O or .dbd.S or .dbd.NZ wherein Z is hydrogen, C.sub.1-6 -alkyl or --CN and R.sup.3 is selected from a group consisting of various structures have been found to exhibit high affinity for various receptor subtypes including the 5-HT.sub.2 receptor, the 5-HT.sub.1A receptor, the alpha.sub.1 receptor the dopamine receptor or a combination of these and may therefore be useful for treating CNS system, cardiovascular system and gastrointestinal disorders.

  通式I的吡哌啉衍生物 其中R.sup.1代表取代苯基，1-或2-二氮杂萘基，氮杂萘基或二氮杂萘基；n为1、2、3或4；X为--O--或 其中R.sup.2为氢、C.sub.1-6-烷基或C.sub.3-8-环烷基；Y为.dbd.O、.dbd.S或.dbd.NZ，其中Z为氢、C.sub.1-6-烷基或--CN，R.sup.3从一组中选择，该组包括各种结构已被发现对各种受体亚型表现出高亲和力，包括5-HT.sub.2受体，5-HT.sub.1A受体，alpha.sub.1受体，多巴胺受体或这些受体的组合，因此可能对治疗中枢神经系统，心血管系统和胃肠道疾病有用。
• Piperazinylalkoxyindanes and acid addition salts thereof
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0021368A1

  公开（公告）日：1981-01-07

  Piperazinylalkoxyindanes having the general formula wherein n is an integer of 3 or 4; R1 is hydrogen, halogen, alkyl, alkoxy, hydroxy, phenyl or nitro; and R2 is phenyl or pyridyl optionally having at least one substituent selected from the group consisting of halogen, trifluoromethyl, alkoxy and alkylcarbonyl, and acid addition salts thereof are disclosed, which have anti-anxiety activity and are effective as sedatives.

  通式如下的哌嗪基烷氧基茚满酮 其中 n 是 3 或 4 的整数；R1 是氢、卤素、烷基、烷氧基、羟基、苯基或硝基；R2 是苯基或吡啶基，可选择具有至少一个从卤素、三氟甲基、烷氧基和烷基羰基组成的组中选出的取代基，本发明公开了这些化合物及其酸加成盐，它们具有抗焦虑活性，可有效用作镇静剂。
• Substituted cyclic amine compounds as 5HT2 antagonists
  申请人：TOA EIYO LTD.

  公开号：EP0661266A1

  公开（公告）日：1995-07-05

  A substituted cyclic amine compound represented by the following general formula (1) wherein each of R¹ to R⁵ represents a hydrogen atom, a hydroxyl group, an alkyl group or the like, D represents a methine moiety, a nitrogen atom or the like, P represents -CR⁶(R⁷)- or -NR⁸-, Q represents a methine moiety or a nitrogen atom, each of T and B is a single bond or represents a methylene moiety, a carbonyl group or the like, n is an integer of 1 to 6 and each of R⁶, R⁷ and R⁸ represents a hydrogen atom, an alkyl group or the like; and synthetic intermediates thereof. The inventive compound is useful in preventing and treating circulatory organ-related diseases such as hypertension, ischemic heart disease, cerebrovascular disease, peripherol circulatory disease and the like.

  由以下通式（1）代表的取代环胺化合物 其中 R¹ 至 R⁵ 各代表氢原子、羟基、烷基或类似物，D 代表甲基、氮原子或类似物，P 代表-CR⁶(R⁷)- 或-NR⁸-，Q 代表甲基或氮原子、T和B各自为单键或代表亚甲基、羰基或类似基团，n为1至6的整数，R⁶、R⁷和R⁸各自代表氢原子、烷基或类似基团；及其合成中间体。 本发明化合物可用于预防和治疗循环器官相关疾病，如高血压、缺血性心脏病、脑血管疾病、外周循环疾病等。
• New 8-aminoalkyl derivatives of purine-2,6-dione with arylalkyl, allyl or propynyl substituents in position 7, their 5-HT1A, 5-HT2A, and 5-HT7 receptor affinity and pharmacological evaluation
  作者：Grażyna Chłoń-Rzepa、Paweł Żmudzki、Grzegorz Satała、Beata Duszyńska、Anna Partyka、Dagmara Wróbel、Magdalena Jastrzębska-Więsek、Anna Wesołowska、Andrzej J. Bojarski、Maciej Pawłowski、Paweł Zajdel

  DOI：10.1016/s1734-1140(13)70960-5

  日期：2013.1

  Background: Our previous studies in a group of arylpiperazine derivatives of 1,3-dimethyl-3,7-dihydro-purine-2,6-diones, aimed at chemical diversification of the purine-2,6-dione by introduction of hydrophobic substituent in a 7- or 8- position or elongation of the linker length between arylpiperazine and purine core, allowed a selection of potent 5-HT1A, 5-HT2A and 5-HT7 receptor ligands displaying anxiolytic and antidepressant properties. Continuing our research in this field, in the present studies we designed a new series of 8-aminoalkylamino (15-35) and 8-arylpiperazinylpropoxy (36-42) derivatives of 7-substituted 1,3-dimethyl-3,7-dihydropurine-2,6-dione as potential 5-HT1A, 5-HT2A and 5-HT7 receptor ligands with potential psychotropic activity. Methods: Radioligand binding assays were employed for determining the affinity and the selectivity profile of the synthesized compounds for native 5-HT1A, 5-HT2A, and cloned 5-HT6 and 5-HT7 receptors. The functional activity of the selected compounds at 5-HT1A and 5-HT2A receptors was tested in the commonly used in vivo models. Antidepressant and anxiolytic properties were evaluated in the forced swim (FST) and the four-plate test (FPT) in mice, respectively. Results: Among the evaluated series, selected 7-benzyl-8-((4-(4-(3-chlorophenyl)piperazin-1-yl)butyl)amino)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione (21), a mixed 5-HT1A/5-HT2A/5-HT7 receptor ligand, produced an antidepressant-like effect in FST, and exerted anxiolytic-like activity in FPT. Another pharmacologically evaluated compound 42 (a mixed 5-HT1A/5-HT7 ligand) slightly, but non-significantly attenuated the immobility time of mice in FST and was devoid of activity in FPT. Conclusions: Study revealed advantage of mixed 5-HT1A/5-HT2A/5-HT7 receptor ligands over 5-HT1A/5-HT7 agents to display antidepressant- and anxiolytic-like activity. Modification of arylalkyl/allyl substituent in position 7 of purine-2,6-dione opens possibility for designing new 5-HT ligands with preserved p electron system and lower molecular weight.
• ——
  作者：KOMOTO TEHRUO、 SATO SUSUMU、 JOSIDA TADAYUKI、 ISOMAEH KADZUO、 KATORI TAIUX+

  DOI：——

  日期：——