1-(1-benzylpiperidin-4-yl)-3-benzoyl thiourea

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(1-benzylpiperidin-4-yl)-3-benzoyl thiourea
• 英文别名: 3-benzoyl-1-(1-benzylpiperidin-4-yl)-2-thiourea；3-benzoyl-1-(1-benzylpiperidin-4-yl)thiourea；N-[(1-benzylpiperidin-4-yl)carbamothioyl]benzamide
• 化学式: C₂₀H₂₃N₃OS
• 分子量: 353.488
• InChiKey: DVQNKOIBZZCQIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-benzylpiperidin-4-yl)-3-benzoyl thiourea 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 1-benzyl-N-[4,5-bis(p-tolyl)thiazol-2-yl]piperidin-4-ylamine
  参考文献：
  名称：

  Benzylpiperidine-Linked Diarylthiazoles as Potential Anti-Alzheimer’s Agents: Synthesis and Biological Evaluation

  摘要：

  A novel series of hybrid molecules were designed and synthesized by fusing the pharmacophoric features of cholinesterase inhibitor donepezil and diarylthiazole as potential multitarget-directed ligands for the treatment of Alzheimer's disease (AD). The compounds showed significant in vitro anticholinesterase (anti-ChE) activity, the most potent compound (44) among them showing the highest activity (IC50 value of 0.30 +/- 0.01 mu M) for AChE and (1.84 +/- 0.03 mu M) for BuChE. Compound 44 showed mixed inhibition of AChE in the enzyme kinetic studies. Some compounds exhibited moderate to high inhibition of AChE-induced A beta(1-42) aggregation and noticeable in vitro antioxidant and antiapoptotic properties. Compound 44 showed significant in vivo anti-ChE and antioxidant activities. Furthermore, compound 44 demonstrated in vivo neuroprotection by decreasing A beta(1-42)-induced toxicity by attenuating abnormal levels of A beta(1-42), p-Tau, cleaved caspase-3, and cleaved PARP proteins. Compound 44 exhibited good oral absorption and was well tolerated up to 2000 mg/kg, po, dose without showing toxic effects.

  DOI：

  10.1021/acs.jmedchem.6b00426
• 作为产物：
  描述：

  哌啶-4-甲酰胺 在 potassium carbonate 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 1-(1-benzylpiperidin-4-yl)-3-benzoyl thiourea
  参考文献：
  名称：

  Benzylpiperidine-Linked Diarylthiazoles as Potential Anti-Alzheimer’s Agents: Synthesis and Biological Evaluation

  摘要：

  A novel series of hybrid molecules were designed and synthesized by fusing the pharmacophoric features of cholinesterase inhibitor donepezil and diarylthiazole as potential multitarget-directed ligands for the treatment of Alzheimer's disease (AD). The compounds showed significant in vitro anticholinesterase (anti-ChE) activity, the most potent compound (44) among them showing the highest activity (IC50 value of 0.30 +/- 0.01 mu M) for AChE and (1.84 +/- 0.03 mu M) for BuChE. Compound 44 showed mixed inhibition of AChE in the enzyme kinetic studies. Some compounds exhibited moderate to high inhibition of AChE-induced A beta(1-42) aggregation and noticeable in vitro antioxidant and antiapoptotic properties. Compound 44 showed significant in vivo anti-ChE and antioxidant activities. Furthermore, compound 44 demonstrated in vivo neuroprotection by decreasing A beta(1-42)-induced toxicity by attenuating abnormal levels of A beta(1-42), p-Tau, cleaved caspase-3, and cleaved PARP proteins. Compound 44 exhibited good oral absorption and was well tolerated up to 2000 mg/kg, po, dose without showing toxic effects.

  DOI：

  10.1021/acs.jmedchem.6b00426

文献信息

• Polymer anchored 3-benzoyl-1-(1-benzylpiperidin-4-yl)-2-thiopseudourea-Pd(II) complex: An efficient catalyst for the copper and solvent free Sonogashira cross-coupling reaction
  作者：Suresh Thogiti、Sai Prathima Parvathaneni、Srinivas Keesara

  DOI：10.1016/j.jorganchem.2016.08.029

  日期：2016.11

  An efficient copper and solvent free Sonogashira cross-coupling reaction catalyzed by polymer supported 3-benzoyl-1-(1-benzylpiperidin-4-yl)-2-thiopseudourea-Pd(II) complex 4 (PS-bpt-Pd) was reported. This inexpensive and simply synthesized heterogeneous catalyst 4 afforded excellent yields of the cross-coupling products under mild reaction conditions. We have achieved high yields for aryl iodide coupling

  报道了由聚合物负载的3-苯甲酰基-1-（1-苄基哌啶-4-基）-2-硫代伪脲-Pd（II）配合物4（PS-bpt-Pd）催化的无铜和无溶剂的Sonogashira交叉偶联反应。。这种廉价且简单合成的非均相催化剂4在温和的反应条件下提供了极佳的交叉偶联产物收率。我们在室温下，无铜和无溶剂的条件下，与末端炔烃的芳基碘化物偶联反应的收率很高。另外，我们还观察到芳基溴化物作为偶联伙伴的产率中等至良好。这种不溶的PS-bpt-Pd（II）催化剂4通过简单的过滤即可轻松回收，并具有稳定的催化活性，最多可重复使用五次。除此之外，非均相Pd（II）络合物甚至可以克量级应用于具有高催化效率的交叉偶联。
• Synthesis, Spectral and Single-Crystal Analyses of New Derivatives of 4-Amino-N-benzylpiperidine
  作者：Ibrahim N. Hassan、Mou’ad A. Tarawneh、Bohari M. Yamin

  DOI：10.14233/ajchem.2015.19174

  日期：——

  Two new compounds of thiourea derivatives of cinnamoyl and benzoylisothiocyanate with 4-amino-N-benzylpiperidine have been successfully synthesized. The new molecules, 1-(1-benzylpiperidine-4-yl)-3-benzoyl thiourea (I) (yield 83 %) and 1-(1-benzylpiperidine-4-yl)-3-(3-phenylacryloyl)thiourea (II) (yield 81%) were characterized by NMR, IR, UV, CHNS-O techniques as well as X-ray diffraction for single crystal. 1H NMR spectra show chemical shift at 10.77-10.80 ppm and 8.98-8.93 ppm were assigned for both dH(N) protons. Whereas, the chemical shift for 13C NMR analysis for C=O and C=S presence at dC 169-179 ppm. The significant stretching bands for n(N-H), n(C=S), n(C=O) and n(C-N) were around 3250, 800, 1650 and 1340 cm-1, respectively. The important chromophore of C=O was observed with a maximum absorption at around 300 nm in the UV spectra. The structures of (I) and (II) were determined via X-ray diffraction analysis for single crystal. Both molecules exhibit monoclinic crystal system and adopt trans-cis configuration with respect to the position of the phenyl and N-benzylpiperidine groups relative to the thione S atom, across their C-N bonds. There is one intramolecular N-H···O hydrogen bonds in both molecules that lead to the formation of pseudo-six-membered, in addition to a pseudo-five-membered ring, C9–H9···S1, in (I) which stabilizes the molecule. In the crystal lattice, the molecules are linked by intermolecular hydrogen bonds C–H···S and C–H···O forming chain network in (I) and polymeric in (II).

  两种新化合物：4-氨基-N-苄基哌啶的肉桂酰和苯甲酰异硫氰酸酯的硫脲衍生物已成功合成。新分子1-(1-苄基哌啶-4-基)-3-苯甲酰硫脲(I)(产率83%)和1-(1-苄基哌啶-4-基)-3-(3-苯基丙烯酰)硫脲(II)(产率81%)，通过NMR、IR、UV、CHNS-O技术以及单晶X射线衍射进行了表征。1H NMR光谱显示，dH(N)质子的化学位移在10.77-10.80 ppm和8.98-8.93 ppm之间。而13C NMR分析中C=O和C=S的化学位移为dC 169-179 ppm。n(N-H)、n(C=S)、n(C=O)和n(C-N)的显著伸缩带分别在3250、800、1650和1340 cm-1附近被观察到。C=O的重要色团在UV光谱中显示出约300 nm的最大吸收。通过单晶X射线衍射分析确定(I)和(II)的结构。两种分子均展现单斜晶系，并在苯基和N-苄基哌啶基团相对于硫烯S原子的位点上采用顺-反构型。两个分子中都有一个分子内N-H···O氢键，导致伪六元环的形成，此外(I)中还有一个伪五元环C9–H9···S1，从而稳定了分子。在晶格中，这些分子通过分子间氢键C–H···S和C–H···O相互连接，形成(I)中的链状网络和(II)中的聚合物结构。
• Ultrasound promoted synthesis, characterization and computational studies of some thiourea derivatives
  作者：Felix Odame、Eric C. Hosten、Kevin Lobb、Zenixole Tshentu

  DOI：10.1016/j.molstruc.2020.128302

  日期：2020.9

  Abstract Synthesis of some thiourea derivatives have been achieved by using ultrasound, the compounds have been characterised using IR, NMR, GC-MS and elemental analysis. The single crystal X-ray structure of N-[(benzyloxy)methanethioyl]benzamide (IV), 1-benzoyl-3-(2-hydroxyethyl)thiourea (V) and 3-benzoyl-1-(1-benzylpiperidin-4-yl)thiourea (VI) has been presented and the bond lengths and bond angles

  摘要 利用超声波合成了一些硫脲衍生物，并用红外、核磁共振、气相色谱-质谱和元素分析对化合物进行了表征。N-[(苄氧基)甲硫酰基]苯甲酰胺(IV)、1-苯甲酰基-3-(2-羟乙基)硫脲(V)和3-苯甲酰基-1-(1-苄基哌啶-4-)的单晶X射线结构基) 硫脲 (VI) 已被提出，键长和键角与计算结果形成对比。还计算和讨论了 HOMO 和 LUMO 能级以及化合物的全局化学反应性描述符。在分子静电势和振动频率计算中获得了化合物 IV 至 VI 的两种共轭体，并且已经讨论了这些。