1-[(4-甲基苯基)甲基]哌啶-4-胺 | 68304-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-[(4-甲基苯基)甲基]哌啶-4-胺
• 英文名称: 1-(p-methylbenzyl)-4-aminopiperidine
• 英文别名: 1-(4-methylbenzyl)-4-piperidinamine；1-(4-methylbenzyl)piperidin-4-amine；1-[(4-methylphenyl)methyl]piperidin-4-amine；1-(4-METHYLBENZYL)-4-PIPERIDINYLAMINE；4-amino-1-(4-methylbenzyl)piperidine；4-amino-N-(4-methylbenzyl)piperidine
• CAS: 68304-96-1
• 化学式: C₁₃H₂₀N₂
• 分子量: 204.315
• InChiKey: BRUKSTGIAUDJQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(4-甲基苯基)甲基]哌啶-4-胺 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 生成 1-[[4-(3-Cyanophenyl)phenyl]methyl]-3-[1-[(4-methylphenyl)methyl]piperidin-4-yl]urea
  参考文献：
  名称：

  新型系列的取代联苯甲基脲衍生物作为MCH-R1拮抗剂，可用于治疗肥胖症。

  摘要：

  我们已经基于取代的联苯甲基尿素核心设计并合成了两个新颖的MCH-R1拮抗剂系列。探索了SAR，表明当联苯甲基和连接基被尿素部分的相同氮取代时，与受体的最佳结合得以实现。化合物1-（3'-氰基-4-联苯甲基）-3-（2-羟基-1,1-二甲基乙基）-1- {2- [1-（4-甲基苄基）-4-哌啶基]乙基}脲2t以43 nM K（i）显示出对MCH-R1的最佳拮抗剂结合活性。

  DOI：

  10.1016/j.bmc.2007.02.049
• 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 、 水 、 乙腈 为溶剂， 生成 1-[(4-甲基苯基)甲基]哌啶-4-胺
  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

• HTS-based discovery and optimization of novel positive allosteric modulators of the α7 nicotinic acetylcholine receptor
  作者：István Ledneczki、Anita Horváth、Pál Tapolcsányi、János Éles、Katalin Dudás Molnár、István Vágó、András Visegrády、László Kiss、Áron Szigetvári、János Kóti、Balázs Krámos、Sándor Mahó、Patrik Holm、Sándor Kolok、László Fodor、Márta Thán、Diána Kostyalik、Ottilia Balázs、Mónika Vastag、István Greiner、György Lévay、Balázs Lendvai、Zsolt Némethy

  DOI：10.1016/j.ejmech.2021.113560

  日期：2021.10

  HTS campaign of the corporate compound collection resulted in a novel, oxalic acid diamide scaffold of α7 nACh receptor positive allosteric modulators. During the hit expansion, several derivatives, such as 4, 11, 17 demonstrated not only high in vitro potency, but also in vivo efficacy in the mouse place recognition test. The advanced hit molecule 11 was further optimized by the elimination of the

  公司化合物收集的 HTS 活动产生了一种新型的 α7 nACh 受体阳性变构调节剂草酸二酰胺支架。在命中膨胀，几个衍生物，如4，11，17证明不仅高体外效力，而且在体内在小鼠地方识别测试功效。先进的命中分子11通过消除推定的诱变芳香胺结构单元而得到进一步优化，该结构单元产生了一个新的氨基甲基吲哚化合物家族。在化合物55 的情况下发现了最平衡的物理化学和药理学特征。对接研究揭示了一个亚基间结合位点是我们的化合物最可能的。55不仅在东莨菪碱诱导的健忘症（小鼠位置识别测试）中，而且在自然遗忘（大鼠新物体识别测试）中表现出良好的认知增强特征。此外，化合物55在具有高转化价值的认知范式中是活跃的，即在大鼠触摸屏视觉辨别测试中。因此，选择55作为先导化合物进行进一步优化。基于获得的有利结果，本发明的氨基甲基吲哚簇可以通过α7 nAChR的正变构调节为认知增强提供可行的方法。
• Anti-prion activities and drug-like potential of functionalized quinacrine analogs with basic phenyl residues at the 9-amino position
  作者：Thuy Nguyen、Yuji Sakasegawa、Katsumi Doh-ura、Mei-Lin Go

  DOI：10.1016/j.ejmech.2011.04.016

  日期：2011.7

  In this paper, we report the synthesis and cell-based anti-prion activity of quinacrine analogs derived by replacing the basic alkyl side chain of quinacrine with 4-(4-methylpiperazin-I-yl)phenyl, (1-benzylpiperidin-4-yl) and their structural variants. Several promising analogs were found that have a more favorable anti-prion profile than quinacrine in terms of potency and activity across different

  在本文中，我们报道了用4-（4-甲基哌嗪-1-基）苯基，（1-苄基哌啶-4- yl）及其结构变体。发现在不同different病毒感染的鼠细胞模型的效价和活性方面，一些有前途的类似物在抗病毒方面比奎纳克林更有利。它们还表现出对人类病毒蛋白片段的更高结合亲和力（hPrP 121–231）比奎纳克林高，并且在PAMPA-BBB分析中的渗透率在CNS渗透候选物范围内。当在过表达Pgp的细胞系上进行双向分析评估时，与奎纳克林相比，一种类似物对Pgp外排活性的敏感性较低。两者合计，结果表明连接到a啶，四氢ac啶和喹啉骨架上的取代9-氨基侧链的重要作用。该侧链的性质影响基于细胞的效能，PAMPA渗透性和对hPrP 121-231的结合亲和力。
• Synthesis and Studies on Anticonvulsant and Antibacterial Activities of 1- Alkyl-4-(4H-1,2,4-triazol-4-yl)piperidine Derivatives
  作者：Yan-Ping Yuan、Shi-Ben Wang、Guo-Hua Gong、Zhe-Shan Quan

  DOI：10.2174/1570180811666140623204022

  日期：2014.8.31

  4-triazol-4-yl)piperidines and 1-alkyl-4-(2H-1,2,4-triazol-3-one-4-yl) piperidines were synthesized and their anticonvulsant and antibacterial activities were evaluated. Pharmacological tests showed that three of the synthesized compounds (6c, 6k, 7m) displayed 100% protection at a dose of 100 mg/kg. 4-(1- Octylpiperidin-4-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (6c) was the most active compound in this study

  两个系列的1-烷基-4-（4H-1,2,4-三唑-4-基）哌啶和1-烷基-4-（2H-1,2,4-三唑-3-一-4-基）合成哌啶并评估其抗惊厥和抗菌活性。药理试验表明，三种合成化合物（6c，6k，7m）在100 mg / kg剂量下显示出100％的保护作用。4-（1-辛基哌啶-4-基）-2,4-二氢-3H-1,2,4-三唑-3-酮（6c）是本研究中活性最高的化合物，ED 50为65.4 mg / kg和TD 50值为241.2 mg / kg，PI值为3.6。四种合成的化合物对革兰氏阳性细菌金黄色葡萄球菌（RN4220，KCTC 209和KCTC 503）表现出有效的抑制活性，尤其是对耐多药临床分离株（MRSA3167 / 3506和QRSA3505 / 3519）具有抑制作用。其中，化合物1-tetradeyl-4-（4H-1,2,4-triazol-4-yl）哌啶（7f）对革兰氏阳性菌株的活性最高（MIC
• [EN] 2-PHENYL-3H-IMIDAZO[4,5-B]PYRIDINE DERIVATES USEFUL AS INHIBITORS OF MAMMALIAN TYROSINE KINASE ROR1 ACTIVITY<br/>[FR] DÉRIVÉS DE 2-PHÉNYL-3H-IMIDAZO[4,5-B]PYRIDINE UTILISÉS COMME INHIBITEURS DE L'ACTIVITÉ DE LA TYROSINE KINASE DE MAMMIFÈRE ROR1
  申请人：KANCERA AB

  公开号：WO2016124553A1

  公开（公告）日：2016-08-11

  A compound of formula (I´) or (I´´) or a pharmaceutically acceptable salt thereof. The compound is an inhibitor of mammalian kinase enzyme activity, including ROR1 tyrosine kinase activity and may be used in the treatment of disorders associated with such activity.

  化合物的化学式（I´）或（I´´）或其药学上可接受的盐。该化合物是哺乳动物激酶酶活性的抑制剂，包括ROR1酪氨酸激酶活性，并可用于治疗与该活性相关的疾病。
• [EN] METHODS AND COMPOSITIONS OF INHIBITING DCN1-UBC12 INTERACTION<br/>[FR] PROCÉDÉS ET COMPOSITIONS D'INHIBITION DE L'INTERACTION DCN1-UBC12
  申请人：ST JUDE CHILDREN'S RES HOSPITAL

  公开号：WO2017049295A1

  公开（公告）日：2017-03-23

  In one aspect, the invention relates to substituted l-phenyl-3-(piperidin-4-yl)urea analogs, derivatives thereof, and related compounds, which are useful as inhibitors of the DCN1-UBC12 interaction inhibitors of DCN1 -mediated cullin-RING ligase activity, methods of making same, pharmaceutical compositions comprising same, methods of treating disorders using the disclosed compounds and compositions, methods of treating disorders associated with a DCN1-UBC12 interaction dysfunction, methods of treating disorders associated with a DCN1-mediated cullin-RING ligase activity dysfunction, methods of male contraception comprising the disclosed compounds and compositions, and kits comprising the disclosed compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在一个方面，本发明涉及替代的l-苯基-3-(哌啶-4-基)脲类似物，其衍生物和相关化合物，这些化合物可用作DCN1-UBC12相互作用抑制剂和DCN1介导的卡林-环形酶活性抑制剂，制备方法，包含这些化合物的药物组合物，使用所披露的化合物和组合物治疗疾病的方法，治疗与DCN1-UBC12相互作用功能障碍相关的疾病的方法，治疗与DCN1介导的卡林-环形酶活性功能障碍相关的疾病的方法，包含所披露的化合物和组合物的男性避孕方法，以及包含所披露的化合物和组合物的试剂盒。本摘要旨在作为在特定领域进行搜索的扫描工具，并不打算限制本发明。