(-)-Win 35981 | 53898-68-3

• 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: (-)-Win 35981
• 英文别名: 2β-carbomethoxy-3β-phenylnortropane；methyl (1R,2S,3S,5S)-3-phenyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS: 53898-68-3
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: JEZUFWYDKGYUCS-DGAVXFQQSA-N

物化性质

• 沸点：
  356.4±42.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-Win 35981 在 potassium carbonate 、 三乙胺 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 氢氟酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 29.25h， 生成
  参考文献：
  名称：

  作为多巴胺转运蛋白探针的氘代[18F]氟乙基托烷类似物：合成和生物学评价

  摘要：

  介绍 多巴胺转运蛋白（DAT）与帕金森病（PD）和其他神经退行性疾病密切相关。DAT的无创成像有助于相关疾病的早期诊断和监测。最近，我们报道了一种氘代[ 18 F]氟乙基托烷类似物[ 18 F]FECNT-d 4作为潜在的DAT PET显像剂。这项工作的目的是通过比较四种氘代[ 18 F]氟乙基托烷衍生物（[ 18 F] 2a-d ）来扩展研究，以开发代谢稳定的 DAT 放射性配体。 方法 合成了四种氟乙基取代的苯基托烷化合物1a-d和氘代化合物2a-d并评估了它们对DAT的IC 50值。[ 18 F]氟乙基配体[ 18 F] 1a-d和[ 18 F] 2a-d是通过一步放射性标记反应从相应的标记前体获得的，并在亲脂性和体外结合亲和力方面进行了研究。然后选择[ 18 F] 1d和[ 18 F] 2d通过体内代谢研究、生物分布、离体放射自显影和microPET 成像研究进行进一步评估。 结果

  DOI：

  10.1016/j.nucmedbio.2023.108334
• 作为产物：
  描述：

  脱水芽子碱甲基酯甲磺酸盐 在 溶剂黄146 、 锌 作用下， 生成 (-)-Win 35981
  参考文献：
  名称：

  [123I] -2β-羰甲氧基-3β-（4-碘苯基）托烷：脑中单胺再摄取位点的高亲和力SPECT放射性示踪剂。

  摘要：

  DOI：

  10.1021/jm00114a027

文献信息

• PROCESS FOR THE PREPARATION OF RADIOIODINATED 3-FLUOROPROPYL-NOR-Beta-CIT
  申请人：MALLINCKRODT LLC

  公开号：US20150087838A1

  公开（公告）日：2015-03-26

  The invention generally provides processes for the preparation of radioiodinated 3-fluoropropyl-nor-β-CIT. In particular, the process uses an arylsilane intermediate, thus avoiding the use of hexamethylditin, and reducing the number of steps previously required for the preparation of radioiodinated 3-fluoropropyl-nor-β-CIT from anhydroecgonine methyl ester. The invention also relates to the alkylation of a nortropane to the corresponding N-(3-fluoropropyl) analogue using 3-fluoropropanal.

  该发明通常提供了用于制备放射性碘化3-氟丙基-去-β-CIT的方法。具体而言，该过程使用芳基硅烷中间体，从而避免使用六甲基锡，减少以前从去水基甲基植物碱制备放射性碘化3-氟丙基-去-β-CIT所需的步骤数量。该发明还涉及利用3-氟丙醛对去幽梗烷烃进行烷基化，形成相应的N-(3-氟丙基)类似物。
• Synthesis and monoamine uptake inhibition of conformationally constrained 2β-carbomethoxy-3β-phenyl tropanes
  作者：Patrick Johannes Riss、René Hummerich、Patrick Schloss

  DOI：10.1039/b902863c

  日期：——

  A series of 2β-carbomethoxy-3β-phenyl tropanes with conformationally constrained nitrogen substituents were synthesized as potential selective dopamine transporter ligands. These novel compounds were examined for their monoamine uptake inhibition potency at the human dopamine transporter (hDAT), the human serotonin transporter (hSERT) and the human noradrenalin transporter (hNET), stably expressed

  合成了一系列具有构象约束的氮取代基的2β-羰甲氧基-3β-苯基托烷，作为潜在的选择性 多巴胺转运体配体。对这些新型化合物进行了检查一元胺 对人体的吸收抑制能力 多巴胺 运输者（hDAT）， 人类 血清素 运输者（hSERT）和人类 去甲肾上腺素 运输者（网络），在人类胚胎肾细胞（HEK）中稳定表达。进行了SAR研究，以确定在C链上延伸的，4-氟化，构象受限的C 4链的贡献。托烷 氮对人 一元胺 转运蛋白的亲和力和选择性。
• Fluoralkenyl nortropanes
  申请人：Emory University

  公开号：US06344179B1

  公开（公告）日：2002-02-05

  Provided are compounds of the following formula: wherein R is C2-C6 mono- or multi-unsaturated hydrocarbon having one or more ethylene, acetylene or allene groups, A is 18 or 19, and X is H or halogen. The compounds of the invention bind to dopamine transporter with high affinity and selectivity and are thus useful as diagnostic and therapeutic agents for diseases associated with dopamine transporter dysfunction. The radiolabeled compounds are useful as imaging agents for visualizing the location and density of dopamine transporter by PET imaging.

  提供的化合物具有以下公式：其中R是具有一个或多个乙烯、乙炔或戊二烯基团的C2-C6单烯烃或多烯烃碳氢化合物，A为18或19，X为H或卤素。该发明的化合物具有高亲和力和选择性地结合多巴胺转运蛋白，因此可用作与多巴胺转运蛋白功能障碍相关的疾病的诊断和治疗药物。放射标记的化合物可用作PET成像来可视化多巴胺转运蛋白的位置和密度。
• Synthesis and Ligand Binding of Nortropane Derivatives:  N-Substituted 2β-Carbomethoxy-3β-(4‘-iodophenyl)nortropane and <i>N</i>-(3-Iodoprop-(2<i>E</i>)-enyl)-2β-carbomethoxy-3β-(3‘,4‘-disubstituted phenyl)nortropane. New High-Affinity and Selective Compounds for the Dopamine Transporter
  作者：Patrick Emond、Lucette Garreau、Sylvie Chalon、Miriam Boazi、Mireille Caillet、Jacques Bricard、Yves Frangin、Laurent Mauclaire、Jean-Claude Besnard、Denis Guilloteau

  DOI：10.1021/jm960795d

  日期：1997.4.1

  Two novel series of iodinated N-substituted analogs of 2 beta-carbomethoxy-3 beta-(4'-iodophenyl)tropane (beta-CIT) and N-(3-iodoprop-(2E)-enyl)-2 beta-carbomethoxy-3 beta-(3',4'-disubstituted phenyl)nortropane were synthesized. They were evaluated for their inhibitory properties on dopamine (DA(T)), serotonin (5-HTT), and norepinephrine (NET) transporters in rat brain homogenates using [H-3]GBR-12935, [H-3]paroxetine, and [H-3]nisoxetine as specific ligands. All new N-substituted analogs of beta-CIT exhibited higher DA(T) selectivity over both 5-HTT and NET than beta-CIT. Moreover compounds with the N-substituents propynyl (6), crotyl (4), 2-bromoprop-(2E)-enyl (5), and 3-iodoprop-(2E)-enyl (3d) showed similar to higher DA(T) affinities than beta-CIT (respectively 14, 15, 30, and 30 nM vs 27 nM). Compound 3d was found to be the most selective DAT agent of this series (5-HTT/DA(T) = 32.0 vs 0.1 for beta-CIT), The N-(3-iodoprop-(2E)-enyl) chain linked to the tropane nitrogen was therefore maintained on the tropane structure, and phenyl substitution was carried out in order to improve DA(T) affinity. K-i values of N-(3-iodoprop-(2E)-enyl)-2 beta-carbomethoxy-3 beta-(3',4'-disubstituted phenyl)nortropanes revealed that phenyl, 4'-isopropyl, and 4'-n-propyl derivatives weakly inhibited specific binding to DA(T), whereas phenyl substitution with 4'-methyl (3c), 3',4'-dichloro (3b), and 4'-iodo (3d) yielded high-DA(T) reuptake agents with increased DA(T) selectivity compared to beta-CIT. These results demonstrate that the combination of a nitrogen and a phenyl substitution yields compounds with high affinity and selectivity for the dopamine transporter which are usable as SPECT markers for DA neurons.
• Chen; Kilts; Camp, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S400-S402
  作者：Chen、Kilts、Camp、Ely、Keil、Malveaux、Votaw、Hoffman、Goodman

  DOI：——

  日期：——