1-phenyl-3-(4-phenylpiperazino)propanol | 157846-64-5

• 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: 1-phenyl-3-(4-phenylpiperazino)propanol
• 英文别名: 1-phenyl-3-(4-phenylpiperazin-1-yl)propan-1-ol
• CAS: 157846-64-5
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: NVLCVVRIEJYTIG-UHFFFAOYSA-N

物化性质

• 沸点：
  469.1±45.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-(4-phenylpiperazino)propanol 在 sodium hydroxide 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 72.17h， 生成 1-[3-(3,4-二甲氧基苯氧基)-3-苯基丙基]-4-苯基哌嗪
  参考文献：
  名称：

  Sharma. V. L.; Bhandari, Kalpana; Chatterjee, S. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 4, p. 393 - 396

  摘要：

  DOI：
• 作为产物：
  描述：

  1-phenylpiperazine hydrochloride 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 1-phenyl-3-(4-phenylpiperazino)propanol
  参考文献：
  名称：

  Sharma. V. L.; Bhandari, Kalpana; Chatterjee, S. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 4, p. 393 - 396

  摘要：

  DOI：

文献信息

• Catalytic Formal Hydroamination of Allylic Alcohols Using Manganese PNP‐Pincer Complexes
  作者：Leandro Duarte de Almeida、Florian Bourriquen、Kathrin Junge、Matthias Beller

  DOI：10.1002/adsc.202100081

  日期：2021.9.7

  Several manganese-PNP pincer catalysts for the formal hydroamination of allylic alcohols are presented. The resulting γ-amino alcohols are selectively obtained in high yields applying Mn-1 in a tandem process under mild conditions.

  介绍了几种用于烯丙醇正式加氢胺化的锰-PNP 钳形催化剂。在温和条件下，采用串联工艺中的Mn-1，选择性地以高产率获得了所得的 γ-氨基醇。
• Synthesis and pharmacological evaluation of carbamic acid 1-phenyl-3-(4-phenyl-piperazine-1-yl)-propyl ester derivatives as new analgesic agents
  作者：Eunhee Chae、Hanju Yi、Yeonjung Choi、Hyeon Cho、Kiho Lee、Hongsik Moon

  DOI：10.1016/j.bmcl.2012.02.023

  日期：2012.4

  A series of carbamic acid 1-phenyl-3-(4-phenyl-piperazine-1-yl)-propyl ester derivatives were synthesized through discovery strategies for balancing target-based in vitro screening and phenotypic in vivo screening. All the newly synthesized compounds were screened for their analgesic activities and compared with standard drug morphine. Among them, compound 44r, a potent analgesic agent that has favorable

  通过平衡基于靶点的体外筛选和表型体内筛选的发现策略，合成了一系列氨基甲酸1-苯基-3-（4-苯基-哌嗪-1-基）-丙基酯衍生物。筛选所有新合成的化合物的镇痛活性，并与标准药物吗啡进行比较。其中，化合物44r是一种有效的镇痛药，在大鼠中具有良好的药代动力学特性，最重要的是，它具有很大的安全系数。我们通过体外和体内功能分析证明了其镇痛活性可能是通过5-HT 2A拮抗作用实现的。因此，可以得出结论，在开发化合物44r方面有足够的进一步研究的空间。 作为止痛药的主要候选药物。
• Propanolamine derivatives, their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0576766A1

  公开（公告）日：1994-01-05

  Compounds of formula I wherein X is phenyl unsubstituted or optionally substituted with one or more cyano, halogeno, halogenoalkyl, C1-6-alkoxy, C1-6-alkyl, C1-5-alkanoyl, C3-5-alkenyl, aryloxy, aralkoxy, amino, C1-6-alkyl mono or disubstituted amino, C1-4-alkanoylamino, carbamoyl, C1-4-alkyl N-mono or disubstituted carbamoyl, C1-4-alkyl substituted with amino, C1-2-alkyl mono or disubstituted amino, N0₂, morpholino or imidazolyl; and R is 3,4-methylenedioxyphenyl, aryl or heteroaryl all of which can be optionally substituted with one or more cyano, halogeno, C1-6-alkyl, C1-6-alkoxy, C2-6-alkenyl, trifluoromethyl, C3-5-alkylene, aryloxy, aralkoxy or C1-6-alkylthio; and R¹ and R² are C1-10-alkyl, C3-7-cycloalkyl, C2-10-alkenyl, C3-6-cycloalkyl-C1-5-alkyl, all of which can be unsubstituted or substituted with C1-5-alkyl, C1-5-alkoxy or cyano; or R¹ and R² together form a 5, 6 or 7 membered ring containing at least one nitrogen atom, or which optionally contains two nitrogen atoms, one or two oxygen atom(s) or one or two sulphur atom(s) or a combination thereof, which ring is unsubstituted or optionally substituted with C1-4-alkyl, C1-4-alkoxy or aryl; and R³, R⁴, R⁵, R⁶, and R⁷ independently are hydrogen, C1-4-alkyl or phenyl; or R⁴ and X together form a carbocyclic ring containing 5 or 6 atoms, or a salt thereof with a pharmaceutically acceptable acid; provided however that R¹ and R² are not C3-7-cycloalkyl, C1-10-alkyl or C2-10-alkenyl which may be straight, branched or cyclic, unsubstituted or substituted with C1-4-alkoxy, aryloxy or cycloalkyl, cyano or cycloalkylalkyl, when X is phenyl substituted with cyano, halogen, halogenalkyl, C1-6-alkoxy, C1-6-alkyl, C1-5-alkanoyl, C3-5-alkylene, aryloxy or aralkoxy, are useful in the treatment of anoxia, traumatic injury, ischemia, migraine, epilepsy, Parkinson's disease, Alzheimer's disease and other neurodegenerative diseases.

  化合物的公式I，其中X是苯基，未取代或可选地取代一个或多个氰基，卤基，卤代烷基，C1-6-烷氧基，C1-6-烷基，C1-5-酰基，C3-5-烯基，芳氧基，芳基氧基，氨基，C1-6-烷基单取代或双取代氨基，C1-4-酰胺基，氨基甲酰基，C1-4-烷基N-单取代或双取代的氨基甲酰基，C1-4-烷基取代氨基，C1-2-烷基单取代或双取代氨基，N0₂，吗啉基或咪唑基；以及R是3,4-亚甲二氧基苯基，芳基或杂环芳基，所有这些都可以可选地取代一个或多个氰基，卤基，C1-6-烷基，C1-6-烷氧基，C2-6-烯基，三氟甲基，C3-5-亚烷基，芳基氧基，芳基氧基或C1-6-烷硫基；以及R¹和R²是C1-10-烷基，C3-7-环烷基，C2-10-烯基，C3-6-环烷基-C1-5-烷基，所有这些都可以未取代或取代C1-5-烷基，C1-5-烷氧基或氰基；或R¹和R²一起形成一个含有至少一个氮原子的5、6或7元环，或可选地含有两个氮原子，一个或两个氧原子或一个或两个硫原子或其组合，该环未取代或可选地取代C1-4-烷基，C1-4-烷氧基或芳基；以及R³、R⁴、R⁵、R⁶和R⁷分别是氢，C1-4-烷基或苯基；或者R⁴和X一起形成一个含有5或6个原子的碳环，或其与药学上可接受的酸的盐；但是，当X是取代有氰基，卤基，卤代烷基，C1-6-烷氧基，C1-6-烷基，C1-5-酰基，C3-5-亚烷基，芳氧基或芳基氧基时，R¹和R²不是C3-7-环烷基，C1-10-烷基或C2-10-烯基，可以是直链，支链或环状，未取代或取代有C1-4-烷氧基，芳氧基或环烷基，氰基或环烷基烷基。这些化合物在缺氧，创伤性损伤，缺血，偏头痛，癫痫，帕金森病，阿尔茨海默病和其他神经退行性疾病的治疗中是有用的。
• Serotonin Reuptake Inhibitors
  申请人：Pinney Kevin G.

  公开号：US20080132514A1

  公开（公告）日：2008-06-05

  A serotonin reuptake inhibitor which can be used in the treatment of depression and which has a decreased occurrence of unwanted side effects. The serotonin reuptake inhibitors are bi-functional organic molecules which combine serotonin transporter reuptake inhibition with serotonin (5-HT, such as 5-HT2A) receptor antagonism in one molecular entity. The serotonin-selective reuptake inhibitor (SSRI) homologue portion of the molecule shows an affinity to the serotonin reuptake transporter (SERT) and has antidepressant properties. The piperazine or piperidine portion of the molecule demonstrates an affinity to 5-HT receptors and restores the undesired side effects of SSRIs.

  一种能够用于治疗抑郁症且不良副作用发生率降低的5-羟色胺再摄取抑制剂。 5-羟色胺再摄取抑制剂是一种双功能的有机分子，它将5-羟色胺转运体再摄取抑制与5-羟色胺（如5-HT2A）受体拮抗结合在一个分子实体中。分子中的5-羟色胺选择性再摄取抑制剂（SSRI）同源物部分显示出对5-羟色胺再摄取转运体（SERT）的亲和力，并具有抗抑郁作用。分子中的哌嗪或哌啶部分显示出对5-HT受体的亲和力，并恢复了SSRI的不良副作用。
• Serotonin reuptake inhibitors
  申请人：Baylor University

  公开号：US07893261B2

  公开（公告）日：2011-02-22

  A serotonin reuptake inhibitor which can be used in the treatment of depression and which has a decreased occurrence of unwanted side effects. The serotonin reuptake inhibitors are bi-functional organic molecules which combine serotonin transporter reuptake inhibition with serotonin (5-HT, such as 5-HT2A) receptor antagonism in one molecular entity. The serotonin-selective reuptake inhibitor (SSRI) homologue portion of the molecule shows an affinity to the serotonin reuptake transporter (SERT) and has antidepressant properties. The piperazine or piperidine portion of the molecule demonstrates an affinity to 5-HT receptors and restores the undesired side effects of SSRIs.

  一种可以用于抑郁症治疗的血清素再摄取抑制剂，具有减少不良副作用的发生率。血清素再摄取抑制剂是双功能有机分子，将血清素转运体再摄取抑制与血清素（5-HT，如5-HT2A）受体拮抗结合在一个分子实体中。分子的血清素选择性再摄取抑制剂（SSRI）同源部分表现出对血清素再摄取转运体（SERT）的亲和力，并具有抗抑郁特性。分子的哌嗪或哌啶部分表现出对5-HT受体的亲和力，并恢复了SSRI的不良副作用。