(4-(氯甲基)苯基)(哌啶-1-基)甲酮 | 185743-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-(氯甲基)苯基)(哌啶-1-基)甲酮
• 英文名称: (4-(chloromethyl)phenyl)(piperidin-1-yl)methanone
• 英文别名: [4-(chloromethyl)phenyl]-piperidin-1-ylmethanone
• CAS: 185743-00-4
• 化学式: C₁₃H₁₆ClNO
• mdl: MFCD08166734
• 分子量: 237.729
• InChiKey: WVQKALIRKRBPTC-UHFFFAOYSA-N

物化性质

• 沸点：
  394.5±25.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-(氯甲基)苯基)(哌啶-1-基)甲酮 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 20.99h， 生成 5-chloro-4-methyl-2-{[4-(piperidine-1-carbonyl)phenyl]methyl}-2,3-dihydro-1λ6,2-thiazole-1,1,3-trione
  参考文献：
  名称：

  Saccharin Derivatives as Inhibitors of Interferon-Mediated Inflammation

  摘要：

  A series of novel, saccharin-based antagonists have been identified for the interferon signaling pathway. Through in vitro high-throughput screening with the Colorado Center for Drug Discovery (C2D2) Pilot Library, we identified hit compound 1, which was the basis for extensive structure-activity relationship studies. Our efforts produced a lead anti-inflammatory compound, tert-butyl N-(furan-2-ylmethyl)-N-{4-[(1,1,3-trioxo-2,3-dihydro-1λ(6),2-benzothiazol-2-yl)methyl]benzoyl}carbamate CU-CPD103 (103), as a potent inhibitor using an established nitric oxide (NO) signaling assay. With further studies of its inhibitory mechanisms, we demonstrated that 103 carries out this inhibition through the JAK/STAT1 pathway, providing a drug-like small molecule inflammation suppressant for possible therapeutic uses.

  DOI：

  10.1021/jm500409k
• 作为产物：
  描述：

  4-氯甲基苯甲酰氯 、 哌啶盐酸盐 以 二氯甲烷 为溶剂， 反应 2.0h， 以0.98 g的产率得到(4-(氯甲基)苯基)(哌啶-1-基)甲酮
  参考文献：
  名称：

  [EN] PYRAN DERVATIVES AS CYP11A1 (CYTOCHROME P450 MONOOXYGENASE 11A1) INHIBITORS
  [FR] DÉRIVÉS DE PYRANE EN TANT QU'INHIBITEURS DE CYP11A1 (CYTOCHROME P450 MONOOXYGÉNASE 11A1)

  摘要：

  公式(I)的化合物，其中R1、R2、R3、R4、R5、R23、R24、L、A和B如权利要求1中定义，或其药用可接受的盐被披露。公式(I)的化合物具有作为细胞色素P450单加氧酶11A1（CYP11A1）抑制剂的使用价值。这些化合物作为药物用于治疗激素受体，尤其是雄激素受体相关的疾病和状况，如前列腺癌。

  公开号：

  WO2018115591A1

文献信息

• Sulfonamides
  申请人：Galley Guido

  公开号：US20060014945A1

  公开（公告）日：2006-01-19

  The invention relates to compounds of the general formula in which R 1 , R 2 , R3, R 4 , R 2′ , R3′, R 4′ , R 5 , and X is —CHR— are as defined in the specification. The invention also provides pharmaceutically acceptable acid addition salts, optically pure enantiomers, racemates and diastereomeric mixtures of such compounds. The invention further provides methods for the treatment of Alzheimer's disease or common cancers.

  该发明涉及一般式化合物，其中R1、R2、R3、R4、R2'、R3'、R4'、R5和X为规范中定义的—CHR—。该发明还提供药学上可接受的酸盐加合物，光学纯对映体，外消旋体和这类化合物的二对映异构体混合物。该发明还提供治疗阿尔茨海默病或常见癌症的方法。
• A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
  作者：Sara Cuadros、Matthew A. Horwitz、Bertrand Schweitzer-Chaput、Paolo Melchiorre

  DOI：10.1039/c9sc00833k

  日期：——

  We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals via an SN2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the precursors. It therefore grants access to open-shell

  我们报告了光诱导的三组分自由基过程，该过程耦合随时可用的烷基氯化物，马来酰亚胺和杂芳族片段，以快速生成具有高非对映异构控制性的复杂手性产物。该方法通过基于S N 2的光化学催化机理产生自由基，这不依赖于前体的氧化还原性质。因此，它可以从底物中获得与经典自由基产生策略不相容或惰性的底壳中间体。该过程的氧化还原中性条件使其对氧化还原敏感的底物具有耐受性，并允许在级联产物中安装多个生物学相关的杂环。
• Phosphonium Ylide-Mediated Programmable Fluorination to Access Mono- and Difluoromethylarenes
  作者：Yu Zheng、Zhen-Zhen Xie、Xian-Chen He、Yan-Shan Chen、Wen-Shuo Cheng、Kai Chen、Hao-Yue Xiang、Xiao-Qing Chen、Hua Yang

  DOI：10.1021/acs.orglett.1c00457

  日期：2021.4.2

  Compounds bearing fluorinated moieties are pervasive in a wide range of pharmaceuticals and agrochemicals. The installation of fluorinated units is a persistently vital task in synthetic chemistry, where facile and manipulable assays are highly demanding. Herein, we establish a general and programmable fluorination strategy for the modular assembly of mono- and difluoromethylarenes through the controllable

  带有氟化部分的化合物在许多药物和农用化学品中普遍存在。氟化单元的安装在合成化学中是一项至关重要的任务，在合成化学中，对简便易行的测定法的要求很高。在这里，我们通过establish的可控去质子化和氟化为单-和二氟甲基芳烃的模块化组装建立了通用且可编程的氟化策略。而且，反应顺序的合理组合允许快速构建多样化的含氟芳烃。
• Synthesis and biological evaluation of 2,4-disubstituted phthalazinones as Aurora kinase inhibitors
  作者：Wei Wang、Xiu Feng、Huan-Xiang Liu、Shi-Wu Chen、Ling Hui

  DOI：10.1016/j.bmc.2018.04.048

  日期：2018.7

  4-disubstituted phthalazinones were synthesized and their biological activities, including antiproliferation, inhibition against Aurora kinases and cell cycle effects were evaluated. Among them, N-cyclohexyl-4-((4-(1-methyl-1H-pyrazol-4-yl)-1-oxophthalazin-2(1H)-yl) methyl) benzamide (12c) exhibited the most potent antiproliferation against five carcinoma cell lines (HeLa, A549, HepG2, LoVo and HCT116

  合成了一系列的2,4-二取代邻苯二氮酮，并评估了它们的生物活性，包括抗增殖，对Aurora激酶的抑制作用和细胞周期效应。其中，N-环己基-4-（（4-（1-甲基-1H-吡唑-4-基）-1-氧酞嗪-2（1H）-基）甲基）苯甲酰胺（12c）表现出最强的抗增殖作用5个癌细胞系（HeLa，A549，HepG2，LoVo和HCT116细胞）的IC50值在2.2-4.6μM之间，而参考化合物VX-680的IC50值在8.5-15.3μM之间。此外，Aurora激酶测定法显示化合物12c是AurA和AurB激酶的有效抑制剂，IC50值分别为118±8.1和80±4.2 nM。分子对接研究表明，化合物12c与AurA和AurB形成更好的相互作用。此外，化合物12c通过调节cyclinB1和cdc2的蛋白质水平在HeLa细胞中诱导G2 / M细胞周期停滞。这些结果表明，12c是用于癌症潜在治疗的有希望的泛极光激酶抑制剂。
• Benzoyl Piperidines/pyrrolidines for enhancing synaptic response
  申请人：The Regents of the University of California

  公开号：US05783587A1

  公开（公告）日：1998-07-21

  Benzoyl piperidines and pyrrolidines and compounds of related structure are disclosed for use in enhancing synaptic responses mediated by AMPA receptors. The compounds are effective in the treatment of subjects suffering from impaired nervous or intellectual functioning due to deficiencies in the number or strength of excitatory synapses or in the number of AMPA receptors. The compounds can also be used for the treatment of non-impaired subjects for enhancing performance in sensory-motor and cognitive tasks which depend on brain networks utilizing AMPA receptors, for improving the performance of subjects with memory deficiencies, for treating depression, alcoholism and schizophrenia, and for improving memory encoding.

  本文揭示了苯甲酰哌啶和吡咯啉以及相关结构化合物的用途，用于增强由AMPA受体介导的突触反应。这些化合物对于治疗因兴奋性突触数量或强度不足或AMPA受体数量不足而导致神经或智力功能受损的受试者非常有效。这些化合物还可用于治疗非受损受试者，以增强依赖于利用AMPA受体的脑网络的感觉运动和认知任务的表现，提高记忆缺陷患者的表现，治疗抑郁症、酗酒和精神分裂症，并改善记忆编码。