TC-2559

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: TC-2559
• 英文别名: (3E)-N-methyl-4-(5-ethoxy-3-pyridinyl)-3-buten-1-amine；(E)-N-methyl-4-[3-(5-ethoxypyridin)yl]-3-buten-1-amine；(E)-4-(5-ethoxypyridin-3-yl)-N-methylbut-3-en-1-amine
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: HFZDMKMXPGRKCK-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二溴吡啶 在 palladium diacetate 盐酸 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 TC-2559
  参考文献：
  名称：

  TC-2559: A novel orally active ligand selective at neuronal acetylcholine receptors

  摘要：

  TC-2559 [(E)-N-Methyl-4-[3-(5-ethoxypyridin)yl]-3-buten-1-amine] is a novel nicotinic agonist markedly more selective than recently reported novel nicotinic receptor Ligands (selectivity ratio for central nervous system (CNS) to peripheral nervous system (PNS)> 4000). TC-2559 competes effectively with [H-3]-nicotine binding (K-i = 5 nM) but not with [I-125]-bungarotoxin( > 50,000 nM). Dopamine release from striatal synaptosomes and ion flux from thalamic synaptosomes indicate that TC-2559 is potent and efficacious in the activation of CNS receptors and significantly reduced glutamate-induced neurotoxicity in vitro. TC-2559 has no detectable effects on muscle and ganglion-type nicotinic acetylcholine receptors at concentrations up to 1 mM. TC-2559 significantly attenuates scopolamine-induced cognitive deficits in a step-through passive avoidance task. Acute and repeated oral dosing of TC-2559 enhances performance in a radial arm maze task. Ln contrast to the effects of equimolar concentrations of (-) nicotine, TC-2559 does not induce hypothermia and locomotor activity is not enhanced following repeated daily administration of 14 days. TC-2559 has a markedly enhanced CNS-PNS selectivity ratio and an intra-CNS selectivity as evidenced by the improved cognition without increased locomotor activity. The in vitro and in vivo studies in the present study suggest that TC-2559 has the desired profile to be further evaluated as a potential therapeutic agent for neurodegenerative diseases. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0014-2999(00)00807-4

文献信息

• [EN] ARYL IMIDAZOLE COMPOUNDS AND THEIR USE AS BETA AMYLOID PRODUCTION INHIBITORS<br/>[FR] COMPOSÉ ARYLIMIDAZOLE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PRODUCTION DE LA PROTÉINE AMYLOÏDE BÊTA
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2010098488A1

  公开（公告）日：2010-09-02

  A compound represented by the formula (I): or a pharmacologically acceptable salt or ester thereof, wherein Ring A represents a triazolyl group or the like which may be substituted, Ring B represents a phenyl group or the like which may be substituted, X1 represents a single bond or the like, R1 and R2 each represent a C1-6 alkyl group or the like, m represents an integer of 0 to 3, and n represents an integer of 0 to 2, is effective as a therapeutic agent for a disease caused by Aβ.

  一种由化学式(I)表示的化合物，或其药理学上可接受的盐或酯，其中环A代表可能被取代的三唑基团或类似物，环B代表可能被取代的苯基团或类似物，X1代表单键或类似物，R1和R2分别代表C1-6烷基或类似物，m代表0到3的整数，n代表0到2的整数，对于由Aβ引起的疾病具有治疗作用。
• MULTI-CYCLIC COMPOUNDS
  申请人：KIMURA Teiji

  公开号：US20090062529A1

  公开（公告）日：2009-03-05

  A compound represented by the formula (I): or a pharmacologically acceptable salt thereof, wherein Ar 1 represents an imidazolyl group or the like which may be substituted with a C1-6 alkyl group, Ar 2 represents a phenyl group or the like which may be substituted with a C1-6 alkoxy group, X 1 represents a double bond or the like and Het represents a triazolyl group or the like which may be substituted with a C1-6 alkyl group or the like, is effective as a therapeutic or prophylactic agent for a disease caused by Aβ.

  一种由化学式(I)表示的化合物或其药理学可接受的盐，其中Ar1代表可用C1-6烷基基团取代的咪唑基团或类似基团，Ar2代表可用C1-6烷氧基团取代的苯基团或类似基团，X1代表双键或类似基团，Het代表可用C1-6烷基基团或类似基团取代的三唑基团或类似基团，对由Aβ引起的疾病具有治疗或预防作用。
• [EN] NITROGEN-CONTAINING FUSED HETEROCYCLIC COMPOUNDS AND THEIR USE AS BETA AMYLOID PRODUCTION INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES CONDENSÉS CONTENANT DE L'AZOTE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PRODUCTION DE LA BÊTA-AMYLOÏDE
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2010098487A1

  公开（公告）日：2010-09-02

  A compound represented by the formula [I]: or a pharmacologically acceptable salt or ester thereof, wherein Ring A represents a five-membered aromatic heterocyclic group or the like fused with a non-aromatic ring group, which may be substituted, Ring B represents a phenyl group or the like which may be substituted, X1 represents a single bond or the like, R1 and R2 each represent a C1-6 alkyl group or the like, m represents an integer of 0 to 3, and n represents an integer of 0 to 2, is effective as a therapeutic agent for a disease caused by Aβ.

  化合物的分子式为[I]：或其药理学可接受的盐或酯，其中环A代表一个五元芳香杂环基团或类似于非芳香环基团的融合物，可以被取代，环B代表一个苯基或类似的基团，可以被取代，X1代表一个单键或类似物，R1和R2分别代表一个C1-6烷基基团或类似物，m表示0到3的整数，n表示0到2的整数，对由Aβ引起的疾病具有治疗作用。
• (3-(5-ethoxypyridin)yl)-alkenyl 1 amine compounds
  申请人：——

  公开号：US05616716A1

  公开（公告）日：1997-04-01

  Patients susceptible to or suffering from central nervous system disorders are treated by administering an effective amount of an aryl substituted olefinic amine compound. Exemplary compounds are (E)-4-[3-(5-ethoxypyridin)yl]-3-butene-1-amine, (E)-N-methyl-4-[3-(5-ethoxyrindin)yl]-3-buten-1-amine.

  患有或易受中枢神经系统疾病影响的患者通过给予一种芳基取代的烯丙胺化合物的有效剂量来治疗。示例化合物包括（E）-4-[3-(5-乙氧基吡啶)基]-3-丁烯-1-胺，（E）-N-甲基-4-[3-(5-乙氧基吡啶)基]-3-丁烯-1-胺。
• [EN] PHARMACEUTICAL COMPOSITIONS FOR PREVENTION AND TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS<br/>[FR] PREPARATIONS PHARMACEUTIQUES POUR LA PREVENTION ET LE TRAITEMENT DE TROUBLES DU SYSTEME NERVEUX CENTRAL
  申请人：R. J. REYNOLDS TOBACCO COMPANY

  公开号：WO1997040011A1

  公开（公告）日：1997-10-30

  (EN) Patients susceptible to or suffering from central nervous system disorders are treated by administering effective amounts of aryl substituted aliphatic amine compounds, aryl substituted olefinic amine compounds or aryl substituted acetylenic amine compounds. A representative compound is (E)-N-methyl-5-(3-pyridinyl)-4-penten-2-amine.(FR) Les patients susceptibles de souffrir de troubles du système nerveux central peuvent être traités par administration de quantités efficaces de composés d'amines aliphatiques à substitution aryle, de composés d'amines oléfiniques à substitution aryle, ou de composés d'amines acétyléniques à substitution aryle. L'un des composés représentatifs est le (E)-N-méthyl-5-(3-pyridinyl)-4-pentène-2-amine.

  (中文) 对于容易患有或患有中枢神经系统疾病的患者，可以通过给予含有芳基取代的脂肪胺化合物、芳基取代的烯丙胺化合物或芳基取代的乙炔胺化合物的有效剂量来进行治疗。其中一种代表性化合物为(E)-N-甲基-5-(3-吡啶基)-4-戊烯-2-胺。