1-(4-氯苄基)-4-哌啶酮 | 21937-61-1

• 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-氯苄基)-4-哌啶酮
• 中文别名: 1-[(4-氯苯基)甲基]哌啶-4-酮
• 英文名称: 1-(4-chlorobenzyl)-4-piperidone
• 英文别名: 1‐(4‐chlorobenzyl)piperidin‐4‐one；1-(4-Chlorobenzyl)piperidin-4-one；1-[(4-chlorophenyl)methyl]piperidin-4-one
• CAS: 21937-61-1
• 化学式: C₁₂H₁₄ClNO
• mdl: MFCD03411616
• 分子量: 223.702
• InChiKey: ZCTWGHYTGOWQSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  1-(4-氯苄基)-4-哌啶酮 在 盐酸 、 air 、 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 C₁₈H₁₉ClN₄
  参考文献：
  名称：

  Spiro[1,2,4-benzotriazine-3(4H),4′-(1′-substituted)piperidines] and related compounds as ligands for sigma receptors

  摘要：

  As analogues of some conformationally restricted spiropiperidine derivatives which are endowed with high affinity for sigma(1), receptor, a set of 16 spiro[1,2,4-benzotriazine-3(4H),4'-(1'-substituted)piperidines] and congeneric compounds was prepared and tested for affinity to a, receptor subtype. All N-arylalkyl substituted derivatives exhibited high affinity for the relevant receptor, with K-i in the low nanomolar range. Affinity for sigma(2) subtype (assayed only for a few representative compounds) was from one to three order of magnitude lower. Spiro[ 1,2,4-benzotriazine-3(4H),4'-(1'-benzyl)piperidine] (2), with a ratio K(i)sigma(2)/K(j)sigma(1) = 7000 should represent the most selective sigma(1), ligand so far described. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01293-4
• 作为产物：
  描述：

  8-(4-chloro-benzyl)-1,4-dioxa-8-aza-spiro[4.5]decane 在 氢溴酸 作用下， 生成 1-(4-氯苄基)-4-哌啶酮
  参考文献：
  名称：

  Spiro[1,2,4-benzotriazine-3(4H),4′-(1′-substituted)piperidines] and related compounds as ligands for sigma receptors

  摘要：

  As analogues of some conformationally restricted spiropiperidine derivatives which are endowed with high affinity for sigma(1), receptor, a set of 16 spiro[1,2,4-benzotriazine-3(4H),4'-(1'-substituted)piperidines] and congeneric compounds was prepared and tested for affinity to a, receptor subtype. All N-arylalkyl substituted derivatives exhibited high affinity for the relevant receptor, with K-i in the low nanomolar range. Affinity for sigma(2) subtype (assayed only for a few representative compounds) was from one to three order of magnitude lower. Spiro[ 1,2,4-benzotriazine-3(4H),4'-(1'-benzyl)piperidine] (2), with a ratio K(i)sigma(2)/K(j)sigma(1) = 7000 should represent the most selective sigma(1), ligand so far described. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01293-4

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
• Allosteric adenosine receptor modulators
  申请人：——

  公开号：US20010047008A1

  公开（公告）日：2001-11-29

  The present invention relates to compounds of formulas (IA) and (IB): 1 the preparation thereof, pharmaceutical formulations thereof, and their use in medicine as allosteric adenosine receptor modulators for uses including protection against hypoxia and ischemia induced injury and treatment of adenosine-sensitive cardiac arrhythmias.

  本发明涉及以下化合物的公式（IA）和（IB）：其制备、药物配方以及在医学中作为变构腺苷受体调节剂的用途，包括保护免受缺氧和缺血引起的损伤以及治疗对腺苷敏感的心律失常。
• Synthesis and Biological Effects of Novel 2-Amino-3-naphthoylthiophenes as Allosteric Enhancers of the A₁ Adenosine Receptor
  作者：Pier Giovanni Baraldi、Romeo Romagnoli、Maria Giovanna Pavani、Maria del Carmen Nuñez、Mojgan Aghazadeh Tabrizi、John C. Shryock、Edward Leung、Allan R. Moorman、Canan Uluoglu、Valeria Iannotta、Stefania Merighi、Pier Andrea Borea

  DOI：10.1021/jm0210212

  日期：2003.2.1

  cycloalkylthiophenes, tetrahydrobenzo[b]thiophene derivatives appeared to be more potent than the dihydrocyclopentadien[b]thiophene counterparts. Some of the most potent compounds were tested at a concentration of 10 microM for their affinity as competitors to the antagonist binding site of CHO cells expressing hA(1), hA(2A), and hA(3) adenosine receptors. None inhibited binding at the hA(2A)AR, but most

  当前的研究描述了一系列新型的2-氨基-3-萘噻吩并在噻吩的4-位和5-位以及萘环上有可变的修饰。以多种方式测量了变构增强子的活性：（1）在表达克隆的人A（C）的中国仓鼠卵巢（CHO）细胞中，在A（1）-腺苷激动剂（CPA）存在的情况下评估对福司柯林刺激的cAMP积累的影响。 1）-腺苷受体（hA（1）AR）; （2）这些化合物取代[（3）H] DPCPX，[（3）H] ZM 241385和[（3）H] MRE 3008F20与表达hA（ 1），hA（2A）和hA（3）腺苷受体；（3）对[（3）H] CCPA与表达hA（1）AR的CHO细胞膜结合的影响，含有天然腺苷A（1）受体的大鼠大脑和人类皮质膜制剂；（4）[（3）H] CCPA从CHO-hA1膜解离的动力学。药理分析比较了各种活性与参考化合物PD 81,723（化合物1）的活性。在CHO：hA（1）分析中，几种化合物似乎比PD 81,7
• Structure‐Based Design and Synthesis of Piperidinol‐Containing Molecules as New <i>Mycobacterium abscessus</i> Inhibitors
  作者：Jérôme Ruyck、Christian Dupont、Elodie Lamy、Vincent Le Moigne、Christophe Biot、Yann Guérardel、Jean‐Louis Herrmann、Mickaël Blaise、Stanislas Grassin‐Delyle、Laurent Kremer、Faustine Dubar

  DOI：10.1002/open.202000042

  日期：2020.3

  using standard chemotherapy. We previously demonstrated that a piperidinol derivative, named PIPD1, is an efficient molecule both against M. abscessus and Mycobacterium tuberculosis, the agent of tuberculosis, by targeting the mycolic acid transporter MmpL3. These results prompted us to design and synthesize a series of piperidinol derivatives and to determine the biological activity against M. abscessus

  非结核分枝杆菌 (NTM) 感染，例如由脓肿分枝杆菌引起的感染，在全球范围内正在增加。由于其固有的耐药性，脓肿分枝杆菌肺部感染通常难以使​​用标准化疗来治愈。我们之前证明，一种名为 PIPD1 的哌啶醇衍生物是一种有效的分子，通过靶向分枝菌酸转运蛋白 MmpL3，对抗脓肿分枝杆菌和结核病病原体结核分枝杆菌。这些结果促使我们设计并合成了一系列哌啶醇衍生物，并确定其对抗脓肿分枝杆菌的生物活性。构效关系（SAR）研究指出了支架上可以承受轻微修改的特定位点。总体而言，这些结果表明 FMD-88 是一种新的有前途的抗脓肿分枝杆菌活性类似物。此外，我们还确定了 PIPD1 的药代动力学特性，并表明腹膜内给药该化合物可产生令人鼓舞的血清浓度和 3.2 小时的消除半衰期。
• Anti-psychotic phthalimidine derivatives
  申请人：Astra Lakemedel Aktiebolag

  公开号：US04289781A1

  公开（公告）日：1981-09-15

  Compounds having antipsychotic activity, characterized by the formula ##STR1## in which formula R.sub.o and R.sub.1 are the same or different and are each selected from hydrogen, halogen, alkyl having 1, 2 or 3 carbon atoms, alkoxy having 1, 2 or 3 carbon atoms, and trifluoromethyl, and R.sub.2 is selected from hydrogen, halogen, alkyl having 1, 2 or 3 carbon atoms, alkoxy having 1, 2 or 3 carbon atoms, and trifluoromethyl, pharmaceutical compositions containing them, and a method for the treatment of psychoses.

  具有抗精神病活性的化合物，其特征为式中的##STR1##其中R.sub.o和R.sub.1相同或不同，分别选择自氢，卤素，具有1、2或3个碳原子的烷基，具有1、2或3个碳原子的烷氧基和三氟甲基，并且R.sub.2选择自氢，卤素，具有1、2或3个碳原子的烷基，具有1、2或3个碳原子的烷氧基和三氟甲基，包含它们的制药组合物和治疗精神病的方法。