托哌酮杂质4 | 1023-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 托哌酮杂质4
• 英文名称: 3-(piperidin-1-yl)-1-(p-tolyl)propan-1-one hydrochloride
• 英文别名: 3-piperidino-1-p-tolyl-propan-1-one; hydrochloride；3-Piperidino-1-p-tolyl-propan-1-on; Hydrochlorid；hydron;1-(4-methylphenyl)-3-piperidin-1-ylpropan-1-one;chloride
• CAS: 1023-20-7
• 化学式: C₁₅H₂₁NO*ClH
• 分子量: 267.799
• InChiKey: GDXXLEKTBGMZDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  托哌酮杂质4 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 23.0h， 以9%的产率得到N,N'-bis[1-(4-methylphenyl)-3-(piperidine-1-yl)propylidene]hydrazine dihydrochloride
  参考文献：
  名称：

  Synthesis of new N,N′-bis[1-aryl-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides and evaluation of their cytotoxicity against human hepatoma and breast cancer cells

  摘要：

  N,N'-Bis[1-aryl-3-(piperidine-1-yl)propylidene] hydrazine dihydrochlorides were synthesized by the reaction of 2 mols of 1-aryl-3-(piperidine-1-yl)-1-propanone hydrochlorides with 1 mol of hydrazine hydrate. Aryl part was C6H5 (P1), 4-CH3C6H4 (P2), 4-CH3OC6H4 (P3), 4-HOC6H4 (P4), 4-ClC6H4 (P5), 3-CH3OC6H4 (P6), 4-FC6H4 (P7) and 4-BrC6H4 (P8). Except P1, all compounds were reported for the first time. The chemical structures were confirmed by UV, H-1 NMR, C-13 NMR and HRMS spectra. P1, P2, P7 and P8 against human hepatoma (Huh7) cells and P1, P2, P4, P5, P6, P7 and P8 against breast cancer (T47D) cells have shown cytotoxicity. P1, P2 and P7 had more potent cytotoxicity against Huh7 cells than the reference compound 5-FU, whereas only P2 was more potent than the 5-FU against T47D cells. Representative compound P7 inhibited the mitochondrial respiration at 144, 264 and 424 mu M concentrations dose-dependantly in liver homogenates. The results suggest that P1, P2, P7 and P8 may serve as model compounds for further synthetic studies.

  DOI：

  10.3109/14756366.2013.795562
• 作为产物：
  描述：

  哌啶 、 聚合甲醛 、 对甲基苯乙酮 以 乙醇 为溶剂， 反应 1.0h， 以70%的产率得到托哌酮杂质4
  参考文献：
  名称：

  Synthesis of3H-tolperisone

  摘要：

  Tolperisone (2) has been tritiated to 50 Ci/mmol specific activity in order to use this compound in the study of muscle relaxant binding. Of the two reaction pathways investigated, hydrogenolytic exchange of aromatic bromine is favored over hydrogenation of a double bond.

  DOI：

  10.1002/(sici)1099-1344(199912)42:12<1125::aid-jlcr266>3.0.co;2-9

文献信息

• Synthesis of Mannich Bases by Two Different Methods and Evaluation of their Acetylcholine Esterase and Carbonic Anhydrase Inhibitory Activities
  作者：Halise I. Gul、Alkan Demirtas、Gokbay Ucar、Parham Taslimi、|lhami Gulcin

  DOI：10.2174/1570180814666161128120612

  日期：2017.4.6

  biological activities including carbonic anhydrase (CA) inhibitory and acetylcholine esterase inhibitory (AChE) activities. Objective: It was aimed to synthesize Mannich bases, 1-aryl-3-(morpholin-4-yl/piperidin-1-yl)-1- propanone hydrochloride, by microwave irradiation and conventional heating methods to compare the methods in terms of reaction times and yields and to investigate their inhibitory effects on

  背景：曼尼希碱是药物化学中的重要化合物。它们具有广泛的生物学活性，包括碳酸酐酶（CA）抑制和乙酰胆碱酯酶抑制（AChE）活性。 目的：采用微波辐射法和常规加热法合成曼尼希碱1-芳基-3-（吗啉-4-基/哌啶-1-基）-1-丙烷盐酸盐，比较反应方法。次数和产量，并研究其对AChE酶和CA同工酶的抑制作用。 方法：使用常规加热和微波辐射方法在不同反应条件下合成曼尼希碱。根据文献方法评估化合物对CA同工酶和AChE的抑制作用。 结果：针对hCA I，II和AChE评估了化合物的IC50和Ki值。与所用参考文献相比，该化合物具有更有效或相等的Ki值。 结论：这项研究对曼尼希基础库的综合策略做出了重要贡献。根据IC50或Ki值，A系列中的化合物6与吗啉和B系列中的15与哌啶对hCA I和/或II同工酶以及A系列中的化合物4和11、13、14、15、16和针对AChE的B系列研究中的18似乎是该研究的主要化合物。
• Synthesis and bioactivity studies of 1-aryl-3-(2-hydroxyethylthio)-1-propanones
  作者：Elif Unluer、Halise Inci Gul、Alkan Demirtas、Hiroshi Sakagami、Naoki Umemura、Muhammet Tanc、Cavit Kazaz、Claudiu T. Supuran

  DOI：10.1080/14756366.2016.1209495

  日期：2016.11.3

  A series of Mannich bases having piperidine moiety were reacted with 2-mercaptoethanol, leading to 1-aryl-3-piperidine-4-yl-1-propanone hydrochlorides. The cytotoxicity and carbonic anhydrase inhibitory activities of these new compounds were evaluated. Among the compounds, only one derivative, nitro substituent bearing EU9, showed an effective cytotoxicity, although weak tumor specificity against human

  使具有哌啶部分的一系列曼尼希碱与2-巯基乙醇反应，得到1-芳基-3-哌啶-4-基-1-丙烷丙酮盐酸盐。评价了这些新化合物的细胞毒性和碳酸酐酶抑制活性。在这些化合物中，只有一种衍生物，即带有EU9的硝基取代基，显示出有效的细胞毒性，尽管针对人口腔恶性细胞和非恶性细胞的肿瘤特异性较弱。该化合物诱导HSC-2口腔鳞状细胞癌细胞凋亡，但不会诱导人牙龈成纤维细胞凋亡。因此，有必要对该铅进行化学修饰，以进一步研究其作为候选药物的作用，并获得具有更好活性曲线的化合物。
• Low-Valent Titanium-Induced Reductive Coupling of Amino Ketones
  作者：Wei-xing Chen、Jun-cai Feng、Zhao-lin Zhou、Jun-hu Zhang

  DOI：10.1055/s-1989-27188

  日期：——

  The reaction of amino ketones with titanium tetrachloride/zinc powder has been studied in tetrahydrofuran and 1,4-dioxane under an argon atmosphere. Symmetrical 1,8-diaminoalkenes 2 were obtained from the corresponding Mannich base hydrochlorides 1 via the intermolecular reductive coupling, and azacycloalkenes 4 were prepared from diketoamines 3 via the intramolecular reductive coupling under similar conditions.

  研究了氨基酮与四氯化钛/锌粉在四氢呋喃和1,4-二恶烷中、氩气氛下的反应。由相应的曼尼希碱盐酸盐1通过分子间还原偶联得到对称1,8-二氨基烯烃2，由二酮胺3通过分子内还原偶联在相似条件下得到氮杂环烯烃4。
• Huang; Hall, Pharmazie, 1996, vol. 51, # 4, p. 199 - 206
  作者：Huang、Hall

  DOI：——

  日期：——
• Kuchar, Miroslav; Brunova, Bohumila; Grimova, Jaroslava, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 12, p. 2896 - 2908
  作者：Kuchar, Miroslav、Brunova, Bohumila、Grimova, Jaroslava、Vanecek, Stanislav、Holubek, Jiri

  DOI：——

  日期：——