3-(1-benzylpiperidin-4-yl)propanal | 120014-31-5

• 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: 3-(1-benzylpiperidin-4-yl)propanal
• 英文别名: 3-(1-benzyl-piperidin-4-yl)-propionaldehyde；1-(Phenylmethyl)-4-piperidinepropanal
• CAS: 120014-31-5
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: UQBIONUYOIPRBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  337.6±15.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  3-(1-benzylpiperidin-4-yl)propanal 在 盐酸 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成 1-(3-(1-Benzyl-piperidin-4yl)-propyl)-1-H-benzoimidazole
  参考文献：
  名称：

  Potent 1,3,4-trisubstituted pyrrolidine CCR5 receptor antagonists: effects of fused heterocycles on antiviral activity and pharmacokinetic properties

  摘要：

  A series of 1,3,4-trisubstituted pyrrolidine CCR5 receptor antagonists containing a variety of fused heterocycles at the 4-position of the piperidine side chain has been discovered, which are orally bioavailable with potent anti-HIV activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.030
• 作为产物：
  描述：

  3-(1-Benzyl-piperidin-4-yl)-propan-1-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以64%的产率得到3-(1-benzylpiperidin-4-yl)propanal
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists

  摘要：

  Immepip, a conformationally constrained analogue of the histamine congener imbutamine, shows high affinity and functional activity on the human H-3 receptor. Using histamine and its homologues as prototypes, other rigid analogues containing either a piperidine or pyrrolidine ring in the side chain were synthesized and tested for their activities at the human H-3 receptor and the closely related H-4 receptor. In the series of piperidine containing analogues, immepip was found to be the most potent H-3 receptor agonist, whereas its propylene analogue 13a was identified as a high-affinity neutral antagonist for the human H-3 receptor. Moreover, replacement of the piperidine ring of immepip by a pyrrolidine ring led to a pair of enantiomers that show a distinct stereoselectivity at the human H-3 and H-4 receptor.

  DOI：

  10.1021/jm030905y

文献信息

• Pyrrolidine modulators of chemokine receptor activity
  申请人：Merck & Co., Inc.

  公开号：US06265434B1

  公开（公告）日：2001-07-24

  The present invention is directed to pyrrolidine compounds of the formula 1: (wherein R1, R2, R3, R4, R5, R6 and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及式1的吡咯烷化合物：（其中R1、R2、R3、R4、R5、R6和n在此处定义），这些化合物可用作趋化因子受体活性的调节剂。具体来说，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。
• Neuroprotective multi-target directed drugs
  申请人：Universitat Autònoma de Barcelona

  公开号：EP2727916A1

  公开（公告）日：2014-05-07

  A new family of multitarget molecules able to interact with acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as with monoamino oxidase (MAO) A and B, has been synthesized. Novel compounds have been designed using a conjunctive approach that combines the benzylpiperidine moiety of the AChE inhibitor donepezil, connected through an oligomethylene linker, to a central nitrogen atom substituted with the propargyl moiety responsible for the MAO inhibition, and a 8-hydroxy-5-methylaminoquinoline functional group, the biometal pro-chelator motif. Overall, the results suggest that the new compounds are promising multitarget drug candidates with potencial impact for AD therapy.

  一种新的多靶分子家族已经合成，能够与乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）以及单胺氧化酶（MAO）A和B相互作用。新颖的化合物是使用联合方法设计的，该方法将AChE抑制剂多奈哌齐的苄哌啶基团与经过寡亚甲基连接的中央氮原子相连接，该中央氮原子上取代了负责MAO抑制的丙炔基团，以及8-羟基-5-甲基氨基喹啉功能基团，生物金属前螯合物基序。总体而言，结果表明这些新化合物是有潜力对阿尔茨海默病治疗产生影响的多靶药物候选物。
• Synthesis and Structure-Activity Relationships of Acetylcholinesterase Inhibitors: 1-Benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine Hydrochloride and Related Compounds
  作者：Hachiro Sugimoto、Youichi Iimura、Yoshiharu Yamanishi、Kiyomi Yamatsu

  DOI：10.1021/jm00024a009

  日期：1995.11

  (anti-AChE) inhibitors such as 1-benzyl-4-[2-(N-benzoylamino)ethyl]piperidine (1), we reported that its rigid analogue, 1-benzyl-4-(2-isoindolin-2-ylethyl)piperidine (5), had more potent activity. We have extended the structure-activity relationship (SAR) study for the rigid analogue and found that the 2-isoindoline moiety in compound 5 can be replaced with a indanone moiety (8) without a major loss

  在发现了一系列新的抗乙酰胆碱酯酶（抗AChE）抑制剂如1-苄基-4- [2-（N-苯甲酰氨基）乙基]哌啶（1）之后，我们报道了其刚性类似物1-苄基-4-（2-异吲哚啉-2-基乙基）哌啶（5）具有更强的活性。我们扩展了对刚性类似物的结构-活性关系（SAR）研究，发现化合物5中的2-异吲哚啉部分可被茚满酮部分（8）取代，而效力没有重大损失。在茚满酮衍生物中，发现1-苄基-4-[（5,6-二甲氧基-1-氧代茚满-2-基）甲基]哌啶（13e）（E2020）（IC50 = 5.7 nM）是最丰富的衍生物之一。有效的抗AChE抑制剂。化合物13e对AChE的选择性亲和力比对丁酰胆碱酯酶大1250倍。体内研究表明，在5 mg / kg（po）的剂量下13e具有比毒扁豆碱更长的作用持续时间，并且在大鼠大脑皮层中乙酰胆碱含量显着增加。我们报告的合成，SAR和拟议的假设绑定网站的13e（E2020）。
• Piperidine and piperazine compounds for use in the treatment of Alzheimer
  申请人：Eisai Co., Ltd.

  公开号：EP1116716A1

  公开（公告）日：2001-07-18

  A cyclic amine compound or a salt thereof is defined by the formula: in which J is (a) an optionally substituted group selected from (1) phenyl, (2) pyridyl, (3) pyrazyl, (4) quinolyl, (5) cyclohexyl, (6) quinoxalyl and (7) furyl; (b) a monovalent or divalent group, in which the phenyl may have a substituent(s) selected from the group consisting of (1) indanyl, (2) indanonyl, (3) indenyl, (4) indenonyl, (5) indanedionyl, (6) tetralonyl, (7) benzosuberonyl, (8) indanolyl and (9) C6H5-CO-CH(CH3)-; (c) a monovalent group derived from a cyclic amide compound; (d) a lower alkyl; or (e) a group of R21-CH=CH- in which R21 is hydrogen or a lower alkoxycarbonyl; B is a bridging group; T is a nitrogen; Q is nitrogen, carbon or >N→0; q is an integer of 1 to 3; K is hydrogen, an optionally substituted phenyl group, an arylalkyl in which the phenyl may have a substituent, cynnamyl, a lower alkyl, pyridylmethyl, a cycloalkylalkyl, adamantanemethyl, furylmethyl, a cycloalkyl, a lower alkoxycarbonyl or an acyl; and ----¯ shows a single bond or a double bond. The compound is useful for the preparation of pharmaceutical compositions and for medicaments effective against senile dementia.

  一个环状胺化合物或其盐的定义公式为：其中J是(a) 选择自(1) 苯基，(2) 吡啶基，(3) 吡唑基，(4) 喹啉基，(5) 环己基，(6) 喹噁啉基和(7) 呋喃基的可选取代基；(b) 一价或二价基团，其中苯基可以具有选自(1) 吲哚基，(2) 吲哚基丙烷基，(3) 茚基，(4) 茚基丙烷基，(5) 吲哚二酮基，(6) 四酮基，(7) 苯并戊二酰基，(8) 吲哚醇基和(9) C6H5-CO-CH(CH3)-的取代基；(c) 源自环状酰胺化合物的一价基团；(d) 较低的烷基；或(e) R21-CH=CH-中R21是氢或较低的烷氧羰基的基团；B是桥接基团；T是氮；Q是氮、碳或>N→0；q是1到3的整数；K是氢、可选取代苯基、芳基烷基，其中苯基可以具有取代基，肉桂酸基，较低的烷基，吡啶甲基，环状烷基烷基，金刚烷基甲基，呋喃基甲基，环状烷基，较低的烷氧羰基或酰基；而----¯表示单键或双键。该化合物用于制备药物组合物和用于治疗老年痴呆症的药物。
• [EN] PYRROLIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] MODULATEURS DE PYRROLIDINE DE L'ACTIVITE DU RECEPTEUR DES CHIMIOKINES
  申请人：MERCK & CO INC

  公开号：WO2000059503A1

  公开（公告）日：2000-10-12

  The present invention is directed to pyrrolidine compounds of formula (I) (wherein R?1, R2, R3, R4, R5, R6¿ and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及式(I)的吡咯烷化合物（其中R1，R2，R3，R4，R5，R6和n的定义如下），它们可用作趋化因子受体活性调节剂。特别地，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。