1-(4-bromobenzyl)piperidin-4-one | 905986-89-2

• 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-(4-bromobenzyl)piperidin-4-one
• 英文别名: N-(4-bromobenzyl)-4-piperidone；1-[(4-Bromophenyl)methyl]piperidin-4-one
• CAS: 905986-89-2
• 化学式: C₁₂H₁₄BrNO
• mdl: MFCD09934519
• 分子量: 268.153
• InChiKey: DJZFFNMXDCTFSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromobenzyl)piperidin-4-one 在 四(三苯基膦)钯 sodium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 30.0h， 生成 3-[4-[(2,4-Dioxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)methyl]phenyl]benzonitrile
  参考文献：
  名称：

  Synthesis and structure–activity relationships of spirohydantoin-derived small-molecule antagonists of the melanin-concentrating hormone receptor-1 (MCH-R1)

  摘要：

  The design, synthesis, and SAR of a series of substituted spirohydantoins are described. Optimization of an in-house screening hit gave compounds that exhibited potent binding affinity and functional activity at MCH-R1. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.01.104
• 作为产物：
  描述：

  dimethyl 3,3'-((4-bromobenzyl)azanediyl)dipropionate 在 盐酸 、 水 、 sodium 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 1-(4-bromobenzyl)piperidin-4-one
  参考文献：
  名称：

  N-（取代的苄基）-3,5-双（亚苄基）-4-哌啶酮：合成和初步抗白血病活性（I）

  摘要：

  通过一系列的迈克尔加成，狄克曼缩合，水解脱羧和羟醛缩合反应，以取代的苄胺为原料合成了一系列新颖的N-（取代的苄基）-3,5-双（亚苄基）-4-哌啶酮5a - 5o。通过1 H NMR，IR，MS技术和元素分析确认了结构。使用白血病细胞系K562进行的基于分析的抗增殖活性研究表明，大多数标题化合物具有抑制白血病K562细胞增殖的高效率，其中化合物5g（IC 50 = 7.81 µg·mL -1），5k（IC 50 = 6.35微克·毫升-1），5l（IC 50 = 7.20 µg·mL -1）和5o（IC 50 = 5.79 µg·mL -1）具有比标准5-氟尿嘧啶（IC 50 = 8.56 µg·mL -1）更好的抑制活性。

  DOI：

  10.1002/cjoc.201180365

文献信息

• Synthesis and Evaluation of Anti-inflammatory N-Substituted 3,5-Bis(2-(trifluoromethyl)benzylidene)piperidin-4-ones
  作者：Zixin Xie、Zaikui Zhang、Shufang Yu、Donghua Cheng、Huan Zhang、Chao Han、Handeng Lv、Faqing Ye

  DOI：10.1002/cmdc.201600606

  日期：2017.2.20

  A total of 24 N‐substituted 3,5‐bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one derivatives were synthesized via aldol condensation, and their anti‐inflammatory activities were evaluated. These compounds were found to have no significant cytotoxicity against mouse bone marrow cells in vitro. However, some compounds, such as c6 (N‐(3‐methylbenzoyl)‐3,5‐bis‐(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one)

  通过羟醛缩合反应合成了24种N-取代的3,5-双（2-（三氟甲基）亚苄基）哌啶-4-酮衍生物，并评估了它们的抗炎活性。发现这些化合物在体外对小鼠骨髓细胞没有明显的细胞毒性。但是，某些化合物，例如c6（N-（3-甲基苯甲酰基）-3,5-双-（2-（三氟甲基）亚苄基）哌啶-4-酮）和c10（N-（2-氯苯甲酰基）-3,5-双（2-（三氟甲基）亚苄基）哌啶-4-酮）通过抑制脂多糖（LPS）刺激的肿瘤坏死因子（TNF）-α表现出有效的抗炎活性，RAW 264.7细胞中白细胞介素-6（IL-6），IL-1β，前列腺素E2（PGE2）和一氧化氮（NO）的产生。用2.5或10 mg kg -1的c6或c10处理可显着降低角叉菜胶诱发的大鼠足水肿，发现这些化合物的抗炎作用优于塞来昔布或消炎痛及其母体化合物C66（2,6-双-（2-（三氟甲基）亚苄基）环己酮）。药代动力学分析表明c6具有比姜黄素更好的生物利
• Novel 2H-pyrazolo[4,3-c]hexahydropyridine derivatives: Synthesis, crystal structure, fluorescence properties and cytotoxicity evaluation against human breast cancer cells
  作者：ChunCheng Pang、ChuanWen Sun、Jing Wang、Di Xiao、Li Ding、HongFei Bu

  DOI：10.1007/s11426-013-4840-x

  日期：2013.6

  A series of novel 2H-pyrazolo[4,3-c]hexahydropyridine derivatives (II) have been designed and synthesized. The target compounds have been identified by elemental analysis and spectral (1H NMR, IR, and MS) data and the absolute configuration of compound (II 1 ) was confirmed by single crystal X-ray diffraction. The cytotoxicity of the target compounds have been evaluated in vitro against two human breast cancer cell lines MCF-7 and MDA-MB-231 by MTT assay. Most compounds exhibited good inhibition, and compounds II 21 (IC50 = 4.7 μM for MCF-7 and IC50 = 9.3 μM for MDA-MB-231), II 33 (IC50 = 2.4 μM for MCF-7 and IC50 = 4.2 μM for MDA-MB-231) and II 40 (IC50 = 3.3 μM for MCF-7 and IC50 =8.6 μM for MDA-MB-231) displayed better inhibitory activity than 5-fluorouracil (IC50 = 4.8 μM for MCF-7 and IC50 = 9.6 μM for MDA-MB-231, respectively). Flow cytometric analysis and DNA fragmentation suggest that II 33 is cytotoxic and able to induce the apoptosis of MCF-7 cells. The fluorescence properties of compounds II 1 , II 6 , II 11 , II 16 , II 23 , II 28 , and II 35 were also studied and compound II 28 afforded the highest photoluminescence quantum yield (38%).

  一系列新型2H-吡唑[4,3-c]六氢吡啶衍生物（II）已被设计和合成。目标化合物通过元素分析和光谱（1H NMR、IR和MS）数据得到确认，化合物（II 1）的绝对构型通过单晶X射线衍射法得以确认。对目标化合物在体外针对两个人乳腺癌细胞株MCF-7和MDA-MB-231进行了MTT法评估其细胞毒性。大多数化合物表现出良好的抑制作用，其中化合物II 21（对MCF-7的IC50为4.7 μM，對MDA-MB-231的IC50为9.3 μM）、II 33（对MCF-7的IC50为2.4 μM，對MDA-MB-231的IC50为4.2 μM）和II 40（对MCF-7的IC50为3.3 μM，對MDA-MB-231的IC50为8.6 μM）显示出比5-氟尿嘧啶（对MCF-7的IC50为4.8 μM，對MDA-MB-231的IC50为9.6 μM）更好的抑制活性。流式细胞仪分析和DNA片段化结果表明，II 33具有细胞毒性，并能诱导MCF-7细胞的凋亡。还研究了化合物II 1、II 6、II 11、II 16、II 23、II 28和II 35的荧光特性，其中化合物II 28的光致发光量子产率最高（38%）。
• Synthesis, Crystal Structure and Anticancer Activities of Tetrahydropyrido[4,3-<i>d</i>]dihydropyrimidine-2-thiones
  作者：Li Ding、Sijia Xue、Jing Li、Di Xiao、Jing Wang、Zhibing Hao、Chuncheng Pang

  DOI：10.1002/cjoc.201200568

  日期：2012.10

  A new series of tetrahydropyrido[4,3‐d]dihydropyrimidine‐2‐thiones (3a–3x) were designed and synthesized. Their structures were confirmed by 1H NMR, IR, MS and elemental analysis, and the conformation of compound 3j was confirmed by X‐ray diffraction. Preliminary bioassays indicated that most of the target compounds presented good antiproliferative activities against leukemic K562 cells, ovarian cancer

  设计并合成了一系列新的四氢吡啶并[4,3 - d ]二氢嘧啶-2-硫酮（3a-3x）。它们的结构通过1 H NMR，IR，MS和元素分析证实，化合物3j的构象通过X射线衍射证实。初步的生物测定表明，大多数目标化合物在体外对白血病K562细胞，卵巢癌HO-8910细胞和肝癌SMMC-7721细胞均具有良好的抗增殖活性。其中化合物3i和3m具有最佳活性，IC 50其中针对白血病K562细胞的分别为3.22和3.65 µg / mL，低于临床实践5–FU的抗癌药物（IC 50 = 8.56 µg / mL）。初步的作用机理研究表明，化合物3i在白血病K562细胞中引起DNA片段化并激活了caspase-3 / 7。
• New (hetero)aryl compounds with MCH antagonistic activity and medicaments comprising these compounds
  申请人：Roth Juergen Gerald

  公开号：US20070111981A1

  公开（公告）日：2007-05-17

  The present invention relates to (hetero)aryl compounds of general formula I wherein the groups and radicals A, B, Q, W, X, Y, Z, R 1 , R 2 , R 4a , R 4b , R 5a , R 5b , have the meanings given in claim 1 . Moreover the invention relates to pharmaceutical compositions containing at least one compound according to the invention. By virtue of their MCH-receptor antagonistic activity the pharmaceutical compositions according to the invention are suitable for the treatment of metabolic disorders and/or eating disorders, particularly obesity, bulimia, anorexia, hyperphagia and diabetes.

  本发明涉及一般式I的（杂）芳基化合物，其中A、B、Q、W、X、Y、Z、R1、R2、R4a、R4b、R5a和R5b基团和基团具有权利要求1中给出的含义。此外，本发明涉及至少含有本发明中的一种化合物的制药组合物。由于其MCH受体拮抗活性，根据本发明的制药组合物适用于治疗代谢紊乱和/或进食障碍，尤其是肥胖症、贪食症、厌食症、暴食症和糖尿病。
• Design, synthesis and antitumor activity evaluation of pyrimidine derivatives containing 4-hydroxypiperidine group
  作者：Lingling Chi、Hao Wang、Fuqiang Yu、Chao Gao、Honglin Dai、Limin Liu、Zhengjie Wang、Yuze Dong、Hongmin Liu、Qiurong Zhang

  DOI：10.1007/s00044-023-03076-0

  日期：2023.10

  pyrimidine derivatives containing the 4-hydroxypiperidine group were designed and synthesized, and the antiproliferative activity of these compounds against four human tumor cell lines (MGC-803, PC-3, A549, H1975) was evaluated by MTT method in vitro. Most of the compounds have moderate anti-proliferative activities, among which compound 17i displayed the most excellent anti-proliferative activity, with

  本研究设计并合成了一系列含有4-羟基哌啶基团的嘧啶衍生物，并通过以下方法评价了这些化合物对四种人肿瘤细胞系（MGC-803、PC-3、A549、H1975）的抗增殖活性。体外MTT法。大多数化合物都具有中等的抗增殖活性，其中化合物17i表现出最优异的抗增殖活性，对H1975细胞的IC 50值为3.89 ± 0.57 µM。初步抗肿瘤机制研究表明，化合物17i可以抑制H1975细胞的集落形成和细胞迁移。此外，化合物17i以剂量依赖性方式诱导H1975细胞凋亡，并使H1975细胞周期阻滞在S期，抑制细胞增殖。这些结果表明化合物17i可能成为进一步研究的有希望的先导物。 图形概要