2,2-diethylpiperazine | 153627-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2,2-diethylpiperazine
• CAS: 153627-84-0
• 化学式: C₈H₁₈N₂
• 分子量: 142.244
• InChiKey: AOELXINWOXDWKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-diethylpiperazine 在 甲酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 4-[(1S,3R)-6-chloro-3-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]-2,2-diethyl-1-methylpiperazine
  参考文献：
  名称：

  Enhanced D1 Affinity in a Series of Piperazine Ring Substituted 1-Piperazino-3-Arylindans with Potential Atypical Antipsychotic Activity

  摘要：

  A study of the effect of aromatic substitution on D-1 and D-2 affinity in a series of previously reported trans-1-piperazino-3-phenylindans shows similar structure-activity relationships for the two receptor sites. 6-Substituted derivatives have affinity for both receptors, and 6-chloro- or B-fluoro-substituted derivatives show preference for D-1 receptors. D-1 affinity and selectivity are significantly increased in a series of new piperazine ring substituted derivatives. Potent D-1 and D-2 antagonism in vivo are confined to derivatives with relatively small substituents in the 2-position of the piperazine ring (e.g. 2-methyl, 2,2-dimethyl, 2-spirocyclobutyl or 2-spirocyclopentyl). Consequently, the effect of aromatic substitution is examined in a series of 1-(2,2-dimethylpiperazino)-3-arylindans. All these compounds except the 4-, 5-, 7- and 4'-chlorosubstituted derivatives have potent D-1 affinity (IC50's below 10 nM) and the majority of the compounds antagonize SK&F 38393-induced circling in 6-OHDA-lesioned rats with ED(50) values about 1 mu mol/kg. In vitro all compounds show preference for D-1 receptors, but in vivo they are equally effective as D-1 and D-2 antagonists. The compounds have high affinity for 5-HT2 receptors and selected compounds show high affinity for alpha(1) adrenoceptors. Furthermore, a subgroup consisting of (-)-38, (-)-39, (-)-41, and (-)-54 does not induce catalepsy in rats. These compounds have the potential of being ''atypical'' antipsychotics and have consequently been selected for further studies. The non-receptor-blocking enantiomers are shown to be inhibitors of DA and NE uptake in accordance with previous observations in compounds unsubstituted in the piperazine ring. Two compounds, (+)-38 and (+)-40, block DA uptake with IC50 values below 10 nM. Finally, the observed structure-activity relationships are discussed in relation to previously published pharmacophore models for D-2 and 5-HT2 receptors. It is concluded that the piperazine substituents might induce a different binding mode at the dopamine receptor sites, perhaps only at the D-1 receptor site.

  DOI：

  10.1021/jm00022a004
• 作为产物：
  描述：

  2-Bromo-2-ethylbutanal 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 25.0 ℃ 、350.0 kPa 条件下， 反应 1.5h， 生成 2,2-diethylpiperazine
  参考文献：
  名称：

  Enhanced D1 Affinity in a Series of Piperazine Ring Substituted 1-Piperazino-3-Arylindans with Potential Atypical Antipsychotic Activity

  摘要：

  A study of the effect of aromatic substitution on D-1 and D-2 affinity in a series of previously reported trans-1-piperazino-3-phenylindans shows similar structure-activity relationships for the two receptor sites. 6-Substituted derivatives have affinity for both receptors, and 6-chloro- or B-fluoro-substituted derivatives show preference for D-1 receptors. D-1 affinity and selectivity are significantly increased in a series of new piperazine ring substituted derivatives. Potent D-1 and D-2 antagonism in vivo are confined to derivatives with relatively small substituents in the 2-position of the piperazine ring (e.g. 2-methyl, 2,2-dimethyl, 2-spirocyclobutyl or 2-spirocyclopentyl). Consequently, the effect of aromatic substitution is examined in a series of 1-(2,2-dimethylpiperazino)-3-arylindans. All these compounds except the 4-, 5-, 7- and 4'-chlorosubstituted derivatives have potent D-1 affinity (IC50's below 10 nM) and the majority of the compounds antagonize SK&F 38393-induced circling in 6-OHDA-lesioned rats with ED(50) values about 1 mu mol/kg. In vitro all compounds show preference for D-1 receptors, but in vivo they are equally effective as D-1 and D-2 antagonists. The compounds have high affinity for 5-HT2 receptors and selected compounds show high affinity for alpha(1) adrenoceptors. Furthermore, a subgroup consisting of (-)-38, (-)-39, (-)-41, and (-)-54 does not induce catalepsy in rats. These compounds have the potential of being ''atypical'' antipsychotics and have consequently been selected for further studies. The non-receptor-blocking enantiomers are shown to be inhibitors of DA and NE uptake in accordance with previous observations in compounds unsubstituted in the piperazine ring. Two compounds, (+)-38 and (+)-40, block DA uptake with IC50 values below 10 nM. Finally, the observed structure-activity relationships are discussed in relation to previously published pharmacophore models for D-2 and 5-HT2 receptors. It is concluded that the piperazine substituents might induce a different binding mode at the dopamine receptor sites, perhaps only at the D-1 receptor site.

  DOI：

  10.1021/jm00022a004

文献信息

• [EN] 1-PIPERAZINO-1,2-DIHYDROINDENE DERIVATIVES<br/>[FR] DERIVES DE 1-PIPERAZINO-1,2-DIHYDROINDENE
  申请人：H. LUNDBECK A/S

  公开号：WO1993022293A1

  公开（公告）日：1993-11-11

  (EN) Trans isomers of 1-piperazino-1,2-dihydroindene compounds having general formula (I), wherein X and Y are hydrogen, halogen, trifluoromethyl, alkyl, alkylthio, trifluoromethylthio, alkoxy, hydroxy, alkylsulfonyl, amino, alkylamino, nitro or cyano; Ar is a phenyl, thienyl or furyl group, each optionally substituted; R1 is hydrogen, or optionally hydroxy substituted alkyl, alkenyl, cycloalkyl or cycloalkylalkyl; R2 is alkyl, alkenyl, cycloalkyl, or cycloalkylalkyl; or R1 and R2 together form a 5 to 7-membered heterocyclic ring fused with the piperazine ring, which ring may be substituted with hydroxy; R3 is hydrogen, alkyl, r alkenyl, cycloalkyl or cycloalkylalkyl; or R2 and R3 together form a 3 to 7-membered carbocyclic ring which is spirofused to the piperazine ring; and R4 is hydrogen or alkyl; have potent antagonistic action on dopamine D1 receptors. The compounds are useful in the treatment of diseases in the central nervous system, in particular psychoses, schizophrenia (positive as well as negative symptoms), anxiety, depression, sleep disturbances, migraine, Parkinson's disease or cocaine abuse.(FR) Trans-isomères de composés de 1-pipérazine-1,2-dihydroindène répondant à la formule générale (I) dans laquelle X et Y représentent hydrogène, halogène, trifluorométhyle, alkyle, alkylthio, trifluorométhylthio, alcoxy, hydroxy, alkylsulfonyle, amino, alkylamino, nitro ou cyano; Ar représente un groupe phényle, thiényle ou furyle, chacun éventuellement substitué; R1 représente hydrogène ou alkyle, alcényle, cycloalkyle ou cycloalkylalkyle éventuellement substitué par hydroxy; R2 représente alkyle, alcényle, cycloalkyle ou cycloalkylalkyle; ou R1 et R2 forment ensemble un noyau hétérocyclique comprenant 5 à 7 éléments, fusionné avec le noyau pipérazine, ce noyau pouvant être substitué par hydroxy; R3 représente hydrogène, alkyle, alcényle, cycloalkyle ou cycloalkylalkyle; ou R2 et R3 forment ensemble un noyau carbocyclique comprenant 3 à 7 éléments qui est spiro-fusionné au noyau pipérazine; et R4 représente hydrogène ou alkyle. Ces composés présentent une activité antagoniste puissante par rapport aux récepteurs de dopamine D1. Ces composés peuvent être utilisés dans le traitement de maladies du système nerveux central, en particulier les psychoses, la schizophénie (symptômes positifs aussi bien que négatifs), l'anxiété, la dépression, les troubles du sommeil, la migraine, la maladie de Parkinson ou l'abus de cocaïne.

  (I)式中的1-哌嗪基-1,2-二氢茚化合物的顺式异构体，其中X和Y为氢、卤素、三氟甲基、烷基、烷硫基、三氟甲基硫基、烷氧基、羟基、烷基磺酰基、氨基、烷基氨基、硝基或氰基；Ar为苯基、噻吩基或呋喃基，每个基团均可选地被取代；R1为氢或可选地被羟基取代的烷基、烯基、环烷基或环烷基烷基；R2为烷基、烯基、环烷基或环烷基烷基；或R1和R2共同形成与哌嗪环融合的5到7元杂环，该环可能被羟基取代；R3为氢、烷基、烯基、环烷基或环烷基烷基；或R2和R3共同形成与哌嗪环融合的3到7元碳环，该环与哌嗪环螺合；R4为氢或烷基。这些化合物对多巴胺D1受体具有强烈的拮抗作用。这些化合物在治疗中枢神经系统疾病，特别是精神病、精神分裂症（正向和负向症状）、焦虑、抑郁、睡眠障碍、偏头痛、帕金森病或可卡因滥用方面有用。
• Piperazines as P2X7 antagonists
  申请人：Betschmann Patrick

  公开号：US20080076924A1

  公开（公告）日：2008-03-27

  Novel compounds of Formula (I) or pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, enantiomers thereof or prodrugs thereof of Formula (I) wherein the substituents are as defined herein, which are useful as therapeutic agents.

  化合物I式的新型化合物或其药学上可接受的盐、代谢物、异构体、对映体或前药，其中取代基如本文所定义，这些化合物可用作治疗剂。
• 1-PIPERAZINO-1,2-DIHYDROINDENE DERIVATIVES
  申请人：H. LUNDBECK A/S

  公开号：EP0638073B1

  公开（公告）日：2000-06-21
• US5807855A
  申请人：——

  公开号：US5807855A

  公开（公告）日：1998-09-15
• [EN] COMPOSITE SEMIPERMEABLE MEMBRANE AND MANUFACTURING METHOD THEREFOR<br/>[FR] MEMBRANE SEMI-PERMÉABLE COMPOSITE ET SON PROCÉDÉ DE FABRICATION<br/>[JA] 複合半透膜およびその製造方法
  申请人：TORAY INDUSTRIES

  公开号：WO2021085600A1

  公开（公告）日：2021-05-06

  本発明の複合半透膜は、多官能脂肪族アミンと多官能芳香族酸ハロゲン化物との縮合体である半芳香族架橋ポリアミドを主成分とする分離機能層を含有し、かつ前記分離機能層が中空状のひだを有し、分離機能層表面の比表面積が１.２以上５．０以下であり、Ｘ線光電子分光測定において、測定された元素中の炭素原子に対する窒素原子と酸素原子の和の割合、Ｃ／（Ｎ＋Ｏ）が２．３以上、４．０以下である分離機能層を備える。