Further exploration of 1-(2-(Bis-(4-fluorophenyl)methoxy)ethyl)piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter.

Lewis D; Zhang Y; Prisinzano T; Dersch CM; Rothman RB; Jacobson AE; Rice KC

首页> 外文期刊>Bioorganic and Medicinal Chemistry Letters >Further exploration of 1-(2-(Bis-(4-fluorophenyl)methoxy)ethyl)piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter.

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Further exploration of 1-(2-(Bis-(4-fluorophenyl)methoxy)ethyl)piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter.

机译：1-（2-（双（（4-氟苯基）甲氧基）乙基）哌嗪的进一步探索（GBR 12909）：N-芳族，N-杂芳族和3-氧合N-苯基丙基取代基对多巴胺和血清素转运蛋白。

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A series of N-aromatic, N-heteroaromatic, and oxygenated N-phenylpropyl derivatives of 1-(2-benzhydryloxyethyl)-piperazine and 1-[2-[bis-(4-fluorophenyl)methoxy]ethyl]piperazine, analogues of GBR 12909 (1a) and 12935 (1b), was synthesized and examined for their dopamine (DAT) and serotonin (SERT) transporter binding properties. One of these compounds, racemic 3-[4-(2-benzhydryloxyethyl)piperazin-1-yl]-1-(3-fluorophenyl)-propan-1-ol (33), had DAT affinity as good as, or better than, GBR 12909 and 12935, and was more selective for DAT over SERT than the GBR compounds. Both trans- (43) and cis- (47) (+/-)-2-(4-[2-[bis-(4-fluorophenyl)-methoxy]ethyl]piperazin-1-ylmethyl)-6- methoxy-1,2,3,4-tetrahydronaphthalen-1-ol had relatively good SERT selectivity and, as well, showed high affinity for SERT.

机译：1-（2-苯甲酰氧基乙基）-哌嗪和1- [2- [双-（双-（4-氟苯基）甲氧基]乙基]哌嗪的一系列N-芳族，N-杂芳族和氧化的N-苯基丙基衍生物，GBR的类似物合成了12909（1a）和12935（1b），并检查了它们的多巴胺（DAT）和血清素（SERT）转运蛋白结合特性。这些化合物中的一种，即外消旋的3- [4-（2-苯甲氧基氧基乙基）哌嗪-1-基] -1-（3-氟苯基）-丙-1-醇（33），其DAT亲和力与或优于，GBR 12909和12935，并且比GBR化合物对SAT的DAT更具选择性。反式（43）和顺式（47）（+/-）-2-（4- [2- [双-（4-氟苯基）-甲氧基]乙基]哌嗪-1-基甲基）-6-甲氧基- 1,2,3,4-四氢萘-1-醇具有相对较好的SERT选择性，并且对SERT也具有很高的亲和力。

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《Bioorganic and Medicinal Chemistry Letters》 |2003年第7期|共5页
作者
Lewis D; Zhang Y; Prisinzano T; Dersch CM; Rothman RB; Jacobson AE; Rice KC;
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正文语种 eng
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Carrier Proteins; Membrane Glycoproteins; Membrane Transport Proteins; Piperazines; 载体蛋白质类; 膜糖蛋白类; 哌嗪类;

机译：Carrier Proteins;Membrane Glycoproteins;Membrane Transport Proteins;Piperazines;载体蛋白质类;膜糖蛋白类;哌嗪类;

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1. Further exploration of 1-(2-(Bis-(4-fluorophenyl)methoxy)ethyl)piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter. [J] . Lewis D, Zhang Y, Prisinzano T, Bioorganic and Medicinal Chemistry Letters . 2003,第7期

机译：1-（2-（双（（4-氟苯基）甲氧基）乙基）哌嗪的进一步探索（GBR 12909）：N-芳族，N-杂芳族和3-氧合N-苯基丙基取代基对多巴胺和血清素转运蛋白。
2. Relationship between in Vivo Occupancy at the Dopamine Transporter and Behavioral Effects of Cocaine,GBR 12909 [1-{2-[Bis-(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine],and Benztropine Analogs [J] . Rajeev I.Desai, Theresa A.Kopajtic, Dawn French, The Journal of Pharmacology and Experimental Therapeutics: Official Publication of the American Society for Pharmacology and Experimental Therapeutics . 2005,第1期

机译：可卡因，GBR 12909 [1- {2- [Bis-（（4-氟苯基）甲氧基]乙基} -4-（3-苯基丙基）哌嗪]和苄索平类似物的行为效应之间的关系在多巴胺转运蛋白上的体内占有率
3. Piperidine Analogues of 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909): High Affinity Ligands for the Dopamine Transporter [J] . Thomas Prisinzano, Elisabeth Greiner, Edward M. Johnson, Journal of Medicinal Chemistry . 2002,第19期

机译：1- [2- [双（4-氟苯基）甲氧基]乙基] -4-（3-苯基丙基）哌嗪的哌啶类似物（GBR 12909）：多巴胺转运蛋白的高亲和力配体
4. Design and Synthesis of 2- and 3-Substituted-3-phenylpropyl Analogs of 1-2-Bis(4-fluorophenyl)methoxyethyl-4-(3-phenylpropyl)piperazine and 1-2-(Diphenylmethoxy)ethyl-4-(3-phenylpropyl)piperazine: Role of Amino Fluoro Hydroxyl Methoxyl Methyl Methylene and Oxo Substituents on Affinity for the Dopamine and Serotonin Transporters [O] . Ling-Wei Hsin, Li-Te Chang, Richard B. Rothman, -1

机译：1- 2- 双（双（4-氟苯基）甲氧基乙基 -4-（3-苯基丙基）哌嗪和1- 2-（二苯基甲氧基）2-和3-取代的3-苯基丙基类似物的设计和合成乙基 -4-（3-苯基丙基）哌嗪：氨基氟羟基甲氧基甲基亚甲基和氧代取代基对多巴胺和5-羟色胺转运蛋白的亲和力

Further exploration of 1-(2-(Bis-(4-fluorophenyl)methoxy)ethyl)piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter.

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