4-(2-hydroxyethyl)-1-(3-phenylpropionyl)piperidine | 168888-49-1

• 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: 4-(2-hydroxyethyl)-1-(3-phenylpropionyl)piperidine
• 英文别名: 1-[4-(2-hydroxyethyl)piperidin-1-yl]-3-phenylpropan-1-one
• CAS: 168888-49-1
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: ABLOMRCXKIPPJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxyethyl)-1-(3-phenylpropionyl)piperidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-(3-phenylpropyl)-4-(2-hydroxyethyl)piperidine
  参考文献：
  名称：

  Piperidine Analogues of 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909):  High Affinity Ligands for the Dopamine Transporter

  摘要：

  A series of 4-[2-[bis(4-fluorophenyl)methoxy]ethylpiperidines were examined for their ability to bind to the dopamine transporter (DAT), the norepinephrine transporter, and the serotonin transporter (SERT). In particular, the role of the N-substituent on affinity and selectivity for the DAT was probed. 4-[2-[Bis(4-fluorophenyl)methoxy]ethyl-1-(2-naphthylmethyl)piperidine was found to possess subnanomolar affinity (K-i = 0.7 nM) and good selectivity for the DAT (SERT/DAT = 323).

  DOI：

  10.1021/jm020264r
• 作为产物：
  描述：

  4-哌啶乙醇 、 3-苯基丙酸 在 sodium hydroxide 、 氯化亚砜 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 生成 4-(2-hydroxyethyl)-1-(3-phenylpropionyl)piperidine
  参考文献：
  名称：

  Azolyl-cyclic amine derivates with immunomodulatory activity

  摘要：

  本文描述了一种具有免疫调节活性的化合物，其化学式为（I），如规范中定义的，或其药学上可接受的盐，包括含有该化合物的药物组合物，以及制备和使用该化合物的过程。

  公开号：

  US05741800A1

文献信息

• AZOLYL-CYCLIC AMINE DERIVATIVES WITH IMMUNOMODULATORY ACTIVITY
  申请人：Knoll AG

  公开号：EP0705258A1

  公开（公告）日：1996-04-10
• US5741800A
  申请人：——

  公开号：US5741800A

  公开（公告）日：1998-04-21
• [EN] AZOLYL-CYCLIC AMINE DERIVATIVES WITH IMMUNOMODULATORY ACTIVITY<br/>[FR] DERIVES D'AMINE AZOLYL-CYCLIQUE A ACTIVITE IMMUNOMODULATRICE
  申请人：KNOLL AG

  公开号：WO1995000507A1

  公开（公告）日：1995-01-05

  (EN) A compound of formula (I) having immunomodulatory activity or a pharmaceutically acceptable salt thereof, in which R1, R2 and R3 are hydrogen; halo; cyano; hydroxy(C1-6)-alkyl; C1-6 alkyl; C1-6 alkoxy; C2-6 alkanoyl; C2-6 alkoxycarbonyl; C2-6 alkoxycarbonyl-(C1-6) alkyl; carboxy; nitro; imidazolyl; carboxy(C1-6)-alkyl; C2-6 alkanoyl-(C1-6)alkyl; C1-6 alkoxy(C1-6)alkyl; NR21R22; R23R24N-(C1-6) alkyl; CONR25R26; R27R28NCO(C1-6)-alkyl; S(O)hR29; optionally substituted phenyl, phenoxy or benzyloxy groups; or R1 and R2 together with the phenyl group to which they are attached form a naphthyl group; or R1 together with X and the phenyl group to which they are attached form a tetrahydronaphthyl group; X is a bond, a sulphur atom, an oxygen atom, vinylene, carbonyl or -NHCO-; alk1 and alk2 represent a C1-6 alkylene chain optionally substituted by one or more C1-4 alkyl groups; b is 0 or 1; Y is a saturated 5 or 6 membered heterocyclic ring containing 1 or 2 nitrogen atoms, optionally substituted by C1-6 alkyl, hydroxy(C1-6)alkyl and (C1-6)alkoxy(C1-6)alkyl; R8 is hydrogen or C1-4alkyl; k is 0 or 1; Z is an optionally substituted aromatic heterocyclic ring system comprising imidazolyl, triazolyl and tetrazolyl, optionally having a benzene ring or a pyridine ring fused thereto, connected to alk2 via a nitrogen atom. Pharmaceutical compositions, processes to make and uses of compounds (I) are claimed.(FR) Composé de la formule (I) à activé immunomodulatrice, ou sel pharmaceutiquement acceptable de ce composé, formule dans laquelle R1, R2 et R3 représentent hydrogène; halo; cyano; hydroxy(C1-6)-alkyle; C1-6 alkyle; C1-6 alcoxy; C2-6alcanoyle; C2-6alcoxycarbonyle; C2-6alcoxycarbonyl-(C1-6)alkyle; carboxy; nitro; imidazolyle; carboxy(C1-6)-alkyle; C2-6alcanoyle-(C1-6)alkyle; C1-6alcoxy(C1-6) alkyle; NR21R22; R23R24N-(C1-6)alkyle, CONR25R26; R27R28NCO(C1-6)-alkyle; S(O)nR29; des groupes phényle, phénoxy ou benzyloxy éventuellement substitués; ou R1 et R2 forment, avec le groupe phényle auquel ils sont rattachés, un groupe naphtyle; ou R1 forme, avec X et le groupe phényle auquel il est rattaché, un groupe tétrahydronaphtyle; X représente une liaison, un atome de soufre, un atome d'oxygène, vinylène, carbonyle ou -NHCO-; alk1 et alk2 représentent une chaîne C1-6alkylène éventuellement substituée par un ou plusieurs groupes C1-4alkyle; b vaut O ou 1; Y représente un hétérocycle à 5 ou 6 éléments contenant 1 ou 2 atomes d'azote, éventuellement substitué par C1-6alkyle, hydroxy(C1-6)-alkyle, et (C1-6)alcoxy (C1-6)alkyle; R8 représente hydrogène ou C1-4 alkyle; K vaut O ou 1; Z représente un système d'hétérocycle aromatique éventuellement substitué comprenant imidazolyle, triazolyle et tétrazolyle, auquel est éventuellement fusionné un cycle benzénique ou un cycle pyoridine, relié à alk2 par un atome d'azote. Des compositions pharmaceutiques, des procédés de production et les utilisations des composés de la formule (I) sont revendiqués.
• Azolyl-cyclic amine derivates with immunomodulatory activity
  申请人：Knoll Aktiengesellachaft

  公开号：US05741800A1

  公开（公告）日：1998-04-21

  A compound of the formula (I), ##STR1## as defined in the specification, having immunomodulatory activity, or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising the compound, and processes to make and to use the compound are described.

  本文描述了一种具有免疫调节活性的化合物，其化学式为（I），如规范中定义的，或其药学上可接受的盐，包括含有该化合物的药物组合物，以及制备和使用该化合物的过程。
• Piperidine Analogues of 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909):  High Affinity Ligands for the Dopamine Transporter
  作者：Thomas Prisinzano、Elisabeth Greiner、Edward M. Johnson、Christina M. Dersch、Jamila Marcus、John S. Partilla、Richard B. Rothman、Arthur E. Jacobson、Kenner C. Rice

  DOI：10.1021/jm020264r

  日期：2002.9.1

  A series of 4-[2-[bis(4-fluorophenyl)methoxy]ethylpiperidines were examined for their ability to bind to the dopamine transporter (DAT), the norepinephrine transporter, and the serotonin transporter (SERT). In particular, the role of the N-substituent on affinity and selectivity for the DAT was probed. 4-[2-[Bis(4-fluorophenyl)methoxy]ethyl-1-(2-naphthylmethyl)piperidine was found to possess subnanomolar affinity (K-i = 0.7 nM) and good selectivity for the DAT (SERT/DAT = 323).