(1-苄基-3-哌啶基)甲醇 | 85387-44-6

• 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-苄基-3-哌啶基)甲醇
• 中文别名: 1-苄基-3-羟甲基哌啶
• 英文名称: (1-benzylpiperidin-3-yl)methanol
• CAS: 85387-44-6
• 化学式: C₁₃H₁₉NO
• mdl: MFCD01452200
• 分子量: 205.3
• InChiKey: GEXYNZFTVPXBBB-UHFFFAOYSA-N

物化性质

• 沸点：
  112-113 °C(Press: 0.5 Torr)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  (1-苄基-3-哌啶基)甲醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (1-benzylpiperidin-2-yl)acetaldehyde
  参考文献：
  名称：

  Novel piperidine .sigma. receptor ligands as potential antipsychotic drugs

  摘要：

  Sigma receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine sigma ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for sigma sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these sigma ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.

  DOI：

  10.1021/jm00101a012
• 作为产物：
  描述：

  烟酸乙酯 在 palladium on activated charcoal 氢气 、 sodium 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 30.0h， 生成 (1-苄基-3-哌啶基)甲醇
  参考文献：
  名称：

  3-[（2-乙氧基苯氧基）甲基]哌啶衍生物。合成和抗抑郁活性。

  摘要：

  合成了3-[（2-乙氧基苯氧基）甲基]哌啶衍生物3-5，并通过利血平相互作用试验筛选了潜在的抗抑郁药，并评估了猪脑突触体组分中生物胺的再摄取抑制作用。此外，还评估了它们的抗惊厥活性（通过戊二唑对映体测试）和近似的急性毒性。体内和体外试验表明，化合物3和5具有与抗抑郁药维洛嗪相当的生物活性。

  DOI：

  10.1021/jm00384a040

文献信息

• SUBSTITUTED BIPIPERIDINYL DERIVATIVES
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：US20160318866A1

  公开（公告）日：2016-11-03

  The invention relates to novel substituted bipiperidinyl derivatives, to processes for their preparation, to their use for the treatment and/or prevention of diseases and to their use for preparing medicaments for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of diabetic microangiopathies, diabetic ulcers on the extremities, in particular for promoting wound healing of diabetic foot ulcers, diabetic heart failure, diabetic coronary microvascular heart disorders, peripheral and cardiac vascular disorders, thromboembolic disorders and ischaemias, peripheral circulatory disturbances, Raynaud's phenomenon, CREST syndrome, microcirculatory disturbances, intermittent claudication, and peripheral and autonomous neuropathies.

  该发明涉及新型取代的双哌啶衍生物，涉及它们的制备方法，涉及它们用于治疗和/或预防疾病以及用于制备治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防糖尿病微血管病变、四肢糖尿病溃疡，特别是促进糖尿病足溃疡愈合、糖尿病心力衰竭、糖尿病冠状微血管心脏疾病、外周和心脏血管疾病、血栓栓塞疾病和缺血、外周循环障碍、雷诺现象、CREST综合征、微循环障碍、间歇性跛行以及外周和自主神经病变的治疗和/或预防。
• Design, synthesis and evaluation of (<i>R</i>)-3-(7-(methyl(7<i>H</i>-pyrrolo[2,3-<i>d</i>]pyrimidin-4-yl)amino)-5-azaspiro[2.4]heptan-5-yl)-3-oxopropanenitrile as a JAK1-selective inhibitor
  作者：Chieyeon Chough、Sunmin Lee、Misuk Joung、Jaemin Lee、Jong Hoon Kim、B. Moon Kim

  DOI：10.1039/c7md00568g

  日期：——

  We discovered a new JAK1-selective inhibitor with a selectivity index of 48 and identified its efficacy in CIA and AIA models.

  我们发现了一种新的选择性JAK1抑制剂，其选择性指数为48，并确定了其在CIA和AIA模型中的有效性。
• Targeting Alzheimer's disease by investigating previously unexplored chemical space surrounding the cholinesterase inhibitor donepezil
  作者：Divan G. van Greunen、Werner Cordier、Margo Nell、Chris van der Westhuyzen、Vanessa Steenkamp、Jenny-Lee Panayides、Darren L. Riley

  DOI：10.1016/j.ejmech.2016.10.036

  日期：2017.2

  A series of twenty seven acetylcholinesterase inhibitors, as potential agents for the treatment of Alzheimer's disease, were designed and synthesised based upon previously unexplored chemical space surrounding the molecular skeleton of the drug donepezil, which is currently used for the management of mild to severe Alzheimer's disease. Two series of analogues were prepared, the first looking at the

  根据之前围绕药物多奈哌齐分子骨架未开发的化学空间，设计和合成了一系列二十七个乙酰胆碱酯酶抑制剂，这些药物可作为治疗阿尔茨海默氏病的潜在药物，目前已用于治疗轻度至重度阿尔茨海默氏病。制备了两个系列的类似物，第一个看待用不同尺寸的饱和含氮环系统取代多奈哌齐中的哌啶环，第二个看待多奈哌齐中茚满酮和哌啶环之间引入不同的连接基。活性最高的类似物5,6-二甲氧基-1-氧代-2,3-二氢-1H-茚满-2-基-1-苄基哌啶-4-羧酸酯（67）的体外IC50值为0.03±0。抗乙酰胆碱酯酶为07μM，未观察到细胞毒性（IC50> 100μM，SH-SY5Y细胞系）。相比之下，多奈哌齐的IC50为0.05±0.06μM，观察到的细胞毒性IC50为15.54±1.12μM。分子建模显示活性和乙酰胆碱酯酶活性位点的计算机内结合之间有很强的相关性。
• N-alkylpiperidine carbamates as potential anti-Alzheimer’s agents
  作者：Urban Košak、Nika Strašek、Damijan Knez、Marko Jukič、Simon Žakelj、Abida Zahirović、Anja Pišlar、Xavier Brazzolotto、Florian Nachon、Janko Kos、Stanislav Gobec

  DOI：10.1016/j.ejmech.2020.112282

  日期：2020.7

  oxidase B (MAO-B)]. Four compounds are very promising: multiple AChE (IC50 = 7.31 μM), BChE (IC50 = 0.56 μM) and MAO-B (IC50 = 26.1 μM) inhibitor 10, dual AChE (IC50 = 2.25 μM) and BChE (IC50 = 0.81 μM) inhibitor 22, selective BChE (IC50 = 0.06 μM) inhibitor 13, and selective MAO-B (IC50 = 0.18 μM) inhibitor 16. Results of enzyme kinetics experiments showed that despite the carbamate group in the structure

  能够与涉及阿尔茨海默氏病（AD）发病机理的单个或多个靶标相互作用的化合物是潜在的抗阿尔茨海默氏病药物。为了开发新的抗阿尔茨海默病药物，我们设计，合成和评估了36种新型N-烷基哌啶氨基甲酸酯，以抑制胆碱酯酶[乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）]和单胺氧化酶[单胺氧化酶A（ MAO-A和单胺氧化酶B（MAO-B）]。四种化合物很有希望：多种AChE（IC50 = 7.31μM），BChE（IC50 = 0.56μM）和MAO-B（IC50 = 26.1μM）抑制剂10，双重AChE（IC50 = 2.25μM）和BChE（IC50 = 0.81μM）抑制剂22，选择性BChE（IC50 = 0.06μM）抑制剂13和选择性MAO-B（IC50 = 0.18μM）抑制剂16。酶动力学实验的结果表明，尽管结构中存在氨基甲酸酯基团，化合物10、13和22是可逆且非时间依赖性的AChE
• Novel 2-Amino-1,4-dihydropyridine Calcium Antagonists. II. Synthesis and Antihypertensive Effects of 2-Amino-1,4-dihydropyridine Derivatives Having N,N-Dialkylaminoalkoxycarbonyl Groups at 3- and/or 5-Position.
  作者：Takashi KOBAYASHI、Teruhiko INOUE、Shigeyoshi NISHINO、Yoshimi FUJIHARA、Kiyoshi OIZUMI、Tomio KIMURA

  DOI：10.1248/cpb.43.797

  日期：——

  potency than those with acyclic amino moieties. Chemical modification studies indicated that the two ester side-chains of 1,4-dihydropyridine at the 3- and 5-position might function in a different manner in relation to the antihypertensive activities. 3-(1-Benzhydrylazetidinited potent and long-lasting antihypertensive effects with gradual onset of action, and is a promising candidate as an antihypertensive

  合成了在3和/或5位上含有N，N，-二烷基氨基烷氧基羰基的新型2-氨基-1,4-二氢吡啶衍生物I，并在自发性高血压大鼠中评估了其降压作用。当叔氨基被引入1,4-二氢吡啶环的3-和/或5-酯侧链时，观察到抗高血压作用的持续时间显着延长。特别地，在3位含有环氨基的化合物比具有无环氨基的化合物显示出更高的效力。化学修饰研究表明，在3和5位的1,4-二氢吡啶的两个酯侧链可能以与抗高血压活性有关的不同方式起作用。