1-(3-[2-(4-氟苯基)-[1,3]二氧杂烷-2-基]丙基)哌嗪 | 55846-41-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3-[2-(4-氟苯基)-[1,3]二氧杂烷-2-基]丙基)哌嗪
• 中文别名: 1-{3-[2-（4-氟苯基）-[1,3]-二氧戊环-2-基]丙基}哌嗪
• 英文名称: 1-(3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl)piperazine
• 英文别名: 4-piperazinyl-1,1-(ethylenedioxy)-1-(4-fluorophenyl)butane；1-[4-(4-Fluorophenyl)-4,4-ethylenedioxybutyl]-piperazine；1-[3-[2-(4-fluorophenyl)-1.3-dioxolan-2-yl]propyl]piperazine；1-(3-(2-(4-Fluorophenyl)-1,3-dioxolan-2-yl)propyl)piperazine；1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperazine
• CAS: 55846-41-8
• 化学式: C₁₆H₂₃FN₂O₂
• 分子量: 294.369
• InChiKey: STZDOTGIRWIQNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  33.7
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1-(3-[2-(4-氟苯基)-[1,3]二氧杂烷-2-基]丙基)哌嗪 在 盐酸 、 sodium carbonate 、 potassium iodide 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 3-(4-Fluoro-benzyl)-4-{4-[4-(4-fluoro-phenyl)-4-oxo-butyl]-piperazin-1-yl}-butyric acid methyl ester
  参考文献：
  名称：

  Synthesis and antidopaminergic activity of some 3-(aminomethyl)tetralones as analogs of butyrophenone

  摘要：

  Starting from beta-benzoylpropionic acid was synthesized 3-(aminomethyl)tetralones in which the amino substituent was 4-(N-piperazinyl)-p-fluorobutyrophenone (14), 4-benzoylpiperidine (15), 4-hydroxy-4-phenylpiperidine (16) or 4-(o-methoxyphenyl)piperazine (17). The possible dopamine antagonist activity of these compounds was investigated in both ''in vitro'' and ''in vivo'' experiments. These compounds potently inhibited [H-3]spiperone binding to D2 striatal receptors and moderately inhibited [H-3]SCH-23390 binding to D1 striatal receptors (K(i)s in the nanomolar and micromolar ranges, respectively). Apomorphine-induced stereotypies and amphetamine group toxicity were antagonized, to different extents, by the compounds under study, with a potency similar to that of haloperidol. Interestingly, no catalepsy was observed after administration of the new compounds (2-8 mg/kg). The most active compounds ''in vivo'' 14 and 15 possessed two butyrophenone pharmacophores. However, the tetralone moiety appeared not critical for their antidopaminergic activity, since all target compounds were less active than haloperidol. These studies provide a pharmacological basis for future research on these new compounds devoid of cataleptogenic activity.

  DOI：

  10.1021/jm00111a046
• 作为产物：
  描述：

  哌嗪 、 2-(3-氯丙基)-2-(4-氟苯基)-1,3-二氧戊烷 以 various solvent(s) 为溶剂， 反应 12.0h， 生成 1-(3-[2-(4-氟苯基)-[1,3]二氧杂烷-2-基]丙基)哌嗪
  参考文献：
  名称：

  Synthesis and antidopaminergic activity of some 3-(aminomethyl)tetralones as analogs of butyrophenone

  摘要：

  Starting from beta-benzoylpropionic acid was synthesized 3-(aminomethyl)tetralones in which the amino substituent was 4-(N-piperazinyl)-p-fluorobutyrophenone (14), 4-benzoylpiperidine (15), 4-hydroxy-4-phenylpiperidine (16) or 4-(o-methoxyphenyl)piperazine (17). The possible dopamine antagonist activity of these compounds was investigated in both ''in vitro'' and ''in vivo'' experiments. These compounds potently inhibited [H-3]spiperone binding to D2 striatal receptors and moderately inhibited [H-3]SCH-23390 binding to D1 striatal receptors (K(i)s in the nanomolar and micromolar ranges, respectively). Apomorphine-induced stereotypies and amphetamine group toxicity were antagonized, to different extents, by the compounds under study, with a potency similar to that of haloperidol. Interestingly, no catalepsy was observed after administration of the new compounds (2-8 mg/kg). The most active compounds ''in vivo'' 14 and 15 possessed two butyrophenone pharmacophores. However, the tetralone moiety appeared not critical for their antidopaminergic activity, since all target compounds were less active than haloperidol. These studies provide a pharmacological basis for future research on these new compounds devoid of cataleptogenic activity.

  DOI：

  10.1021/jm00111a046

文献信息

• Piperazine derivatives and pharmaceutical composition containing them
  申请人：Sandoz Ltd.

  公开号：US04565816A1

  公开（公告）日：1986-01-21

  Piperazine derivatives or pharmaceutically acceptable acid addition salts thereof are useful as neuroleptic, anti-hypertensive or bradycardic agents.

  哌嗪衍生物或其药用可接受的酸盐可用作抗精神病药、降压药或减慢心率药。
• 2-piperazinyl-quinazoline derivatives and pharmaceutical compositions
  申请人：Sandoz Ltd.

  公开号：US04588725A1

  公开（公告）日：1986-05-13

  2-Piperazinyl-quinazolines or pharmaceutically acceptable acid addition salts thereof are useful as neuroleptic and anti-hypertensive agents.

  2-哌嗪基喹唑啉或其药用可接受的酸盐可用作神经阻滞剂和降压药。
• 1-3-(4-Fluorobenzoyl)propyl-4-substituted phenoxy ethyl piperazine
  申请人：Kali-Chemie Aktiengesellschaft

  公开号：US03966735A1

  公开（公告）日：1976-06-29

  Piperazine derivatives having the following general formula ##EQU1## in which n is 2 or 3, X is an oxy or thio radical, and A and B are each a radical of the group consisting of phenyl radicals containing at most three substituents of the group consisting of nitro, trifluoromethyl, halogen, cyano, and alkyl, alkoxy, alkylthio, acyl, and alkylsulfonyl radicals containing at most 6 carbon atoms, and similar cycloalkyl and cycloalkylalkyl radicals, their acid addition salts, processes for their production, and pharmaceutical compositions containing the same. The compounds have a very favorable action on the central nervous system and are effective agents for the treatment of anxiety states, psychoses, emotional disturbances, aggressive tendencies, and can be used generally for the treatment of psychiatrically disturbed and psychoneurotic patients.

  哌嗪衍生物具有以下一般公式##EQU1##其中n为2或3，X为氧基或硫基，A和B分别为苯基基团，最多含有三个取代基，所述取代基包括硝基、三氟甲基、卤素、氰基、烷基、烷氧基、烷硫基、酰基和最多含有6个碳原子的烷基磺酰基基团，以及类似的环烷基和环烷基烷基基团，它们的酸盐，其生产方法，以及含有它们的药物组合物。这些化合物对中枢神经系统有非常有利的作用，是治疗焦虑状态、精神病、情绪障碍、攻击性倾向的有效药物，并且通常可用于治疗精神紊乱和神经症患者。
• 2-PIPERAZIN-1-YL-4H-1,3-BENZOTHIAZIN-4-ONE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF MAMMALIAN INFECTIONS
  申请人：Makarov Vadim

  公开号：US20130245007A1

  公开（公告）日：2013-09-19

  The present invention relates to new 2-piperazin-1-yl-4H-1,3-benzothiazin-4-one derivatives and their use for the treatment of mammalian infections caused by bacteria, especially diseases like tuberculosis (TB), Buruli ulcer and leprosy that result from infection with closely related mycobacteria. (I).

  本发明涉及新的2-哌嗪-1-基-4H-1,3-苯并噻唑-4-酮衍生物及其用于治疗由细菌引起的哺乳动物感染，特别是由与结核分枝杆菌密切相关感染引起的疾病，如结核病（TB）、布鲁利溃疡和麻风病。
• Development of Predictive Classification Models for Whole Cell Antimycobacterial Activity of Benzothiazinones
  作者：Sebastian Schieferdecker、Freddy A. Bernal、K. Philip Wojtas、François Keiff、Yan Li、Hans-Martin Dahse、Florian Kloss

  DOI：10.1021/acs.jmedchem.2c00098

  日期：2022.5.12

  against Mycobacterium tuberculosis. However, relationships between their structural properties and whole cell activity remain poorly predictable. Herein, we present the synthesis and antimycobacterial evaluation of a diverse set of BTZs. High potency was predominantly achieved by piperidine and piperazine substitutions, whereupon three compounds were identified as promising candidates, showing preferable

  硝基苯并噻嗪酮 (BTZ) 是一类非常有效的抗结核分枝杆菌的抗生素. 然而，它们的结构特性和全细胞活性之间的关系仍然很难预测。在此，我们介绍了多种 BTZ 的合成和抗分枝杆菌评估。高效力主要通过哌啶和哌嗪取代来实现，因此三种化合物被确定为有希望的候选物，显示出较好的代谢稳定性。效力和计算的结合能之间缺乏相关性表明靶抑制不是获得合适的抗分枝杆菌剂的唯一要求。相比之下，通过广泛验证的机器学习模型成功地完成了全细胞活动类别的预测。通过对大量报告的 BTZ 进行 >70% 的正确类别预测，进一步验证了卓越模型的性能。