4-(4-Oxo-piperidin-1-ylmethyl)-benzonitrile | 1016863-24-3

• 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: 4-(4-Oxo-piperidin-1-ylmethyl)-benzonitrile
• 英文别名: 4-[(4-Oxopiperidin-1-yl)methyl]benzonitrile
• CAS: 1016863-24-3
• 化学式: C₁₃H₁₄N₂O
• mdl: MFCD09949127
• 分子量: 214.267
• InChiKey: IEQBRFVCIRGZLX-UHFFFAOYSA-N

物化性质

• 沸点：
  384.3±32.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-Oxo-piperidin-1-ylmethyl)-benzonitrile 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 1-[4-(4,5-Dihydro-1H-imidazol-2-yl)-benzyl]-4-[4-(4,5-dihydro-1H-imidazol-2-yl)-benzylidene]-piperidine
  参考文献：
  名称：

  Trypanocidal Activity of Conformationally Restricted Pentamidine Congeners

  摘要：

  A series of conformationally restricted congeners of pentamidine in which the flexible pentyl bridge of pentamidine was replaced by trans-1,2-bismethylenecyclopropyl, phenyl, pyridinyl, piperazinyl, homopiperazinyl, and piperidinyl groups were synthesized. The compounds were evaluated for trypanocidal activity in vitro and in vivo against one drug-sensitive and three drug-resistant trypanosome isolates. The DNA binding affinity of the compounds was also studied using calf thymus DNA and poly(dA-dT). The nature of the linker influenced the DNA binding affinity as well as the trypanocidal activity of the compounds. trans-1,2-Bis(4-amidinophenoxymethylene)cyclopropane (1) was over 25-fold more potent than pentamidine against the drug-resistant isolate KETRI 243As-10-3, albeit with comparable DNA binding affinity. NN'-Bis(4-amidinophenyl)homopiperazine (8) was the most potent trypanocide in vitro against all four trypanosome isolates studied, but N,N'-bis(4-amidinophenyl)piperazine (6) was the most effective agent in vivo against both drug-sensitive and drug-resistant trypanosomes.

  DOI：

  10.1021/jm020375q
• 作为产物：
  描述：

  对氰基溴化苄 在 吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 4-(4-Oxo-piperidin-1-ylmethyl)-benzonitrile
  参考文献：
  名称：

  Synthesis and anti-pneumocystis carinii activity of piperidine-linked aromatic diimidazolines

  摘要：

  A series of novel piperidine-linked aromatic diimidazolines (3-7) have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii drug, Pentamidine. These compounds significantly inhibited the growth of Pneumocystis carinii in culture at 1 mu g/mL. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00373-3

文献信息

• Construction of NH‐Unprotected Spiropyrrolidines and Spiroisoindolines by [4+1] Cyclizations of γ‐Azidoboronic Acids with Cyclic <i>N</i> ‐Sulfonylhydrazones
  作者：Lucía López、María‐Paz Cabal、Carlos Valdés

  DOI：10.1002/anie.202113370

  日期：2022.1.10

  N-sulfonylhydrazones of cyclic ketones are readily transformed into NH-free spirocyclic pyrrolidines and isoindolines by reaction with γ-azidoboronic acids. The transition-metal-free transformation is widely applicable and represents a new disconnection towards spirocyclic pyrrolidines. The application of the reaction in the modification of natural steroids and other biorelevant molecules highlights

  通过与 γ-叠氮硼酸反应，环状酮的N-磺酰腙很容易转化为不含 NH 的螺环吡咯烷和异二氢吲哚。不含过渡金属的转变具有广泛的适用性，代表了对螺环吡咯烷的新分离。该反应在修饰天然类固醇和其他生物相关分子中的应用突出了该方法的合成有用性。
• Novel multifunctional tacrine–donepezil hybrids against Alzheimer's disease: Design synthesis and bioactivity studies
  作者：Gülşah Bayraktar、Manuela Bartolini、Maria Laura Bolognesi、Mumin Alper Erdoğan、Güliz Armağan、Ece Bayır、Aylin Şendemir、Donatella Bagetta、Stefano Alcaro、Vildan Alptüzün

  DOI：10.1002/ardp.202300575

  日期：——

  (BChE) with IC50 values in the low micromolar range. Kinetic studies on the most potent cholinesterase (ChE) inhibitors within the series showed a mixed-type inhibition mechanism on both enzymes. Also, the docking studies indicated that the compounds inhibit ChEs by dual binding site (DBS) interactions. Notably, tacrine–donepezil hybrids also exhibited significant neuroprotection against H2O2-induced

  合成了一系列他克林-多奈哌齐杂化物作为潜在的多功能抗阿尔茨海默病（AD）化合物。为此，将他克林和多奈哌齐的苄基哌啶部分与腙基团融合，以获得他克林-多奈哌齐杂合体的小型文库。与设计一致，所有化合物均表现出对乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BChE) 的抑制活性，IC 50值在低微摩尔范围内。该系列中最有效的胆碱酯酶 (ChE) 抑制剂的动力学研究表明，这两种酶具有混合型抑制机制。此外，对接研究表明这些化合物通过双结合位点 (DBS) 相互作用抑制 ChE。值得注意的是，他克林-多奈哌齐杂合体在接近其对 ChE 的 IC 50值的浓度下，对分化的人神经母细胞瘤 (SH-SY5Y) 细胞系中 H 2 O 2诱导的细胞死亡也表现出显着的神经保护作用，并表现出高至中等的血脑屏障(BBB) 人脑微血管内皮细胞 (HBEC-5i) 的通透性。此外，该化合物对人肝细胞癌细胞系(HepG2)和
• Synthesis and anti-pneumocystis carinii activity of piperidine-linked aromatic diimidazolines
  作者：Tien L. Huang、Qian Zhang、Angele T. White、Sherry F. Queener、Marilyn S. Bartlett、James W. Smith、Isaac O. Donkor

  DOI：10.1016/0960-894x(96)00373-3

  日期：1996.9

  A series of novel piperidine-linked aromatic diimidazolines (3-7) have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii drug, Pentamidine. These compounds significantly inhibited the growth of Pneumocystis carinii in culture at 1 mu g/mL. Copyright (C) 1996 Elsevier Science Ltd
• FILAMIN A-BINDING ANTI-INFLAMMATORY ANALGESIC
  申请人：Burns Barbier Lindsay

  公开号：US20110105484A1

  公开（公告）日：2011-05-05

  A compound, its pharmaceutically acceptable salt, a composition containing the same and method of treatment that can provide analgesia and/or reduce inflammation are disclosed. A contemplated compound has a structure that corresponds to Formula A, wherein G, W, Q, Z, D, E, F, K, Y, d, e, f, k, n, m, and circle B and all R groups are defined within.
• FILAMIN A BINDING ANTI-INFLAMMATORY AND ANALGESIC
  申请人：Burns Barbier Lindsay

  公开号：US20110105481A1

  公开（公告）日：2011-05-05

  A compound or its pharmaceutically acceptable salt, optionally including both individual enantiomeric forms, a racemate, diastereomers and mixtures thereof, composition and method are disclosed that can provide analgesia and reduce inflammation. A contemplated compound has a structure that corresponds to Formula A, wherein the R group substituents, d, e, f, k, n, m, D, E, F, K, G, P, Q, W, and Z are defined within.