2-(4-(naphthalen-1-yl)piperazin-1-yl)ethanamine | 283147-75-1

• 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-(4-(naphthalen-1-yl)piperazin-1-yl)ethanamine
• 英文别名: 2-[4-(1-naphthyl)-1-piperazinyl]ethanamine；2-(4-naphthalen-1-ylpiperazin-1-yl)ethanamine
• CAS: 283147-75-1
• 化学式: C₁₆H₂₁N₃
• 分子量: 255.363
• InChiKey: MBPUXARSVLMTGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-(naphthalen-1-yl)piperazin-1-yl)ethanamine 、 7-甲氧基-2-萘满酮 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 1,2-二氯乙烷 、 甲醇 为溶剂， 反应 12.33h， 以56%的产率得到7-methoxy-N-(2-(4-(naphthalen-1-yl)piperazin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-amine
  参考文献：
  名称：

  Development of (S)-N⁶-(2-(4-(Isoquinolin-1-yl)piperazin-1-yl)ethyl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]-thiazole-2,6-diamine and Its Analogue as a D3 Receptor Preferring Agonist: Potent in Vivo Activity in Parkinson’s Disease Animal Models

  摘要：

  Here we report structure-activity relationship study of a novel hybrid series of compounds where structural alteration of aromatic hydrophobic moieties connected to the piperazine ring and bioisosteric replacement of the aromatic tetralin moieties were carried out, Binding assays were carried out with HEK-293 cells expressing either D2 or D3 receptors with tritiated spiperone to evaluate inhibition constants (K-i). Functional activity of selected compounds in stimulating GTP gamma S binding was assessed with CHO cells expressing human D2 receptors and AtT-20 cells expressing human D3 receptors. SAR results identified compound (-)-24c (D301) as one of the lead molecules with preferential agonist activity for D3 receptor (EC50 (GTP gamma S); D3 = 0.52 nM; D2/D3 (EC50): 223). Compounds (-)-24b and (-)-24c exhibited potent radical scavenging activity. The two lead compounds, (-)-24b and (-)-24c, exhibited high in vivo activity in two Parkinson's disease (PD) animal models, reserpinized rat model and 6-OHDA induced unilaterally lesioned rat model. Future studies will explore potential use of these compounds in the neuroprotective therapy for PD.

  DOI：

  10.1021/jm901184n
• 作为产物：
  描述：

  2-{2-[4-(1-naphthyl)-1-piperazinyl]ethyl}-1H-isoindole-1,3(2H)-dione 在 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 2-(4-(naphthalen-1-yl)piperazin-1-yl)ethanamine
  参考文献：
  名称：

  Derivatives of piperidinyl-and piperazinyl-alkyl carbamates, preparation methods thereof and application of same in therapeutics

  摘要：

  对应于通式（I）的化合物：其中A=N或CR2；R2═H、F、OH、CN、CF3、C1-6-烷基、C12-6-烷氧基；n=2或3，当A=N时m=2；n=1、2或3，当A=CR2时m=1或2；B=共价键或C1-8-烷基；R1=可选择取代的杂环芳基；R3═CHR4CONHR5；R4═H或C1-6-烷基；R5═H、C1-6-烷基、C3-7-环烷基、C3-7-环烷基-C1-C6-烷基；以碱、酸盐、水合物或溶剂化合物的形式存在。其治疗用途

  公开号：

  US20060089344A1

文献信息

• THERAPEUTIC USES OF DERIVATIVES OF PIPERIDINYL- AND PIPERAZINYL-ALKYL CARBAMATES
  申请人：ABOUABDELLAH Ahmed

  公开号：US20070142350A1

  公开（公告）日：2007-06-21

  Therapeutic uses of a compound corresponding to the general formula (I): in which A=N or CR 2 ; R 2 =H, F, OH, CN, CF 3 , C 1-6 -alkyl, C 1-6 -alkoxy; n=2 or 3 and m=2 when A=N; n=1, 2 or 3 and m=1 or 2 when A=CR 2 ; B=covalent bond or C 1-8 -alkylene; R 1 =optionally substituted heteroaryl; R 3 =CHR 4 CONHR 5 ; R 4 =H or C 1-6 -alkyl; R 5 =H, C 1-6 -alkyl, C 3-7 -cycloalkyl, C 3-7 -cycloalkyl-C 1 -C 6 -alkylene; in the form of a base, an acid-addition salt, a hydrate or a solvate.

  化合物的治疗用途对应于通式（I）：其中A = N或CR2; R2 = H，F，OH，CN，CF3，C1-6-烷基，C1-6-烷氧基; n = 2或3，当A = N时，m = 2; n = 1,2或3，当A = CR2时，m = 1或2; B = 共价键或C1-8-烷基; R1 = 可选取代的杂环芳基; R3 = CHR4CONHR5; R4 = H或C1-6-烷基; R5 = H，C1-6-烷基，C3-7-环烷基，C3-7-环烷基-C1-C6-烷基; 以碱、酸盐、水合物或溶剂化合物的形式。
• USE OF BINDING PARTNERS FOR 5-HT5 RECEPTORS FOR THE TREATMENT OF NEURODEGENERATIVE AND NEUROPSYCHIATRIC DISORDERS
  申请人：Garcia-Ladona Francisco Javier

  公开号：US20120196301A1

  公开（公告）日：2012-08-02

  The present invention relates to the use of binding partners for 5-HT5 receptors for the treatment of neuropathological, in particular neurodegenerative and/or neuropsychiatric, disorders, which can occur, in particular, in cerebral ischemia, stroke, epilepsy and seizures in general, chronic schizophrenia, other psychotic disorders, dementia, in particular Alzheimer's dementia, demyelinizing disorders, in particular multiple sclerosis, and brain tumors. The invention also relates to processes for the identification and characterization of such binding partners, in particular in the form of screening processes.

  本发明涉及使用与5-HT5受体结合的配体治疗神经病理学，特别是神经退行性和/或神经精神疾病，这些疾病可以在脑缺血、中风、癫痫和一般性抽搐、慢性精神分裂症、其他精神疾病、痴呆，特别是阿尔茨海默病、脱髓鞘性疾病，特别是多发性硬化症和脑肿瘤中发生。本发明还涉及用于鉴定和表征此类配体的过程，特别是以筛选过程的形式。
• THERAPEUTIC USES OF DERIVATIVES OF PIPERIDINYL-AND PIPERIDINYL-ALKYL CARBAMATES
  申请人：Abouabdellah Ahmed

  公开号：US20120004207A1

  公开（公告）日：2012-01-05

  Compound corresponding to the general formula (I): in which A=N or CR 2 ; R 2 ═H, F, OH, CN, CF 3 , C 1-6 -alkyl, C 1-6 -alkoxy; n=2 or 3 and m=2 when A=N; n=1, 2 or 3 and m=1 or 2 when A=CR 2 ; B=covalent bond or C 1-8 -alkylene; R 1 =optionally substituted heteroaryl; R 3 ═CHR 4 CONHR 5 ; R 4 ═H or C 1-6 -alkyl; R 5 ═H, C 1-6 -alkyl, C 3-7 -cycloalkyl, C 3-7 -cycloalkyl-C 1 -C 6 -alkylene; in the form of a base, an acid-addition salt, a hydrate or a solvate. Therapeutic uses thereof.

  化合物的通式为(I)，其中A=N或CR2；R2═H、F、OH、CN、CF3、C1-6-烷基、C1-6-烷氧基；n=2或3，当A=N时，m=2；n=1、2或3，当A=CR2时，m=1或2；B=共价键或C1-8-亚烷基；R1=可选择取代的杂环芳基；R3═CHR4CONHR5；R4═H或C1-6-烷基；R5═H、C1-6-烷基、C3-7-环烷基、C3-7-环烷基-C1-C6-亚烷基。以碱、酸加合盐、水合物或溶剂化合物的形式存在。它们的治疗用途。
• Therapeutic uses of derivatives of piperidinyl- and piperazinyl-alkyl carbamates
  申请人：Sanofi-Aventis

  公开号：US08034818B2

  公开（公告）日：2011-10-11

  Therapeutic uses of a compound corresponding to the general formula (I): in which A=N or CR2; R2=H, F, OH, CN, CF3, C1-6-alkyl, C1-6-alkoxy; n=2 or 3 and m=2 when A=N; n=1, 2 or 3 and m=1 or 2 when A=CR2; B=covalent bond or C1-8-alkylene; R1=optionally substituted heteroaryl; R3=CHR4CONHR5; R4=H or C1-6-alkyl; R5=H, C1-6-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-C6-alkylene; in the form of a base, an acid-addition salt, a hydrate or a solvate.

  化合物的治疗用途对应于一般式（I）：其中A = N或CR2; R2 = H，F，OH，CN，CF3，C1-6-烷基，C1-6-烷氧基; n = 2或3，当A = N时，m = 2; n = 1、2或3，当A = CR2时，m = 1或2; B = 共价键或C1-8-亚烷基; R1 = 可选取代的杂环芳基; R3 = CHR4CONHR5; R4 = H或C1-6-烷基; R5 = H，C1-6-烷基，C3-7-环烷基，C3-7-环烷基-C1-C6-亚烷基; 以盐酸盐、水合物或溶剂化合物的形式出现。
• Radiolabelled alkylamino-benzothiazole and -benzoxazole derivatives and their use as D4 ligands
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1325917A1

  公开（公告）日：2003-07-09

  The present invention concerns the radiolabelled compounds of formula the N-oxide forms, the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein X is O or S; n is 2, 3, 4 or 5; R1 is hydrogen, C1-6alkyl, C1-6alkyloxy or halo; R2 is hydrogen, C1-6alkyl, phenyl, phenylC1-6alkyl or phenylcarbonyl; R3 and R4 each independently are selected from hydrogen, halo, nitro, C1-6alkyl, C1-6alkyloxy, haloC1-6alkyl, aminosulfonyl, mono- or di(C1-4alkyl)aminosulfonyl; or R3 and R4 may also be taken together to form a bivalent radical of formula -CH=CH-CH=CH- , characterized in that the compound has at least one halo which is a radioactive isotope of iodine, bromine or fluorine, or has at least one 11C-atom or tritium atom ; it further relates to a process of marking dopamine D4 receptor sites and a process for imaging an organ.

  本发明涉及放射性标记的式化合物 其中X为O或S；n为2、3、4或5；R1为氢、C1-6烷基、C1-6烷氧基或卤代；R2 是氢、C1-6烷基、苯基、苯基 C1-6 烷基或苯基羰基； R3 和 R4 各自独立地选自氢、卤素、硝基、C1-6烷基、C1-6烷氧基、卤代 C1-6 烷基、氨磺酰基、单-或二(C1-4烷基)氨磺酰基；或 R3 和 R4 也可以结合在一起形成式-CH=CH-CH=CH-的二价基，其特征在于该化合物具有至少一个卤素，该卤素是碘、溴或氟的放射性同位素，或具有至少一个 11C 原子或氚原子；它还涉及一种标记多巴胺 D4 受体位点的工艺和一种器官成像工艺。