Nor-CBT | 189950-17-2

• 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: Nor-CBT
• 英文别名: 2β-carbomethoxy-3β-(4'-bromophenyl)nortropane；3β-(4'-bromophenyl)nortropane
• CAS: 189950-17-2
• 化学式: C₁₅H₁₈BrNO₂
• 分子量: 324.217
• InChiKey: LMRGRSBZWRBHCS-DGAVXFQQSA-N

物化性质

• 沸点：
  397.1±42.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Nor-CBT 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of front bridged tricyclic 3β-(4′-halo or 4′-methyl)phenyltropanes bearing methylene or carbomethoxymethylene on the bridge to the 2β-position

  摘要：

  A series of front bridged tricyclic 3 beta-(4'-halo or 4'-methyl)phenyltropanes bearing methylene or carbomethoxymethylene on the bridge to the 2 beta-position was synthesized, and their binding affinities were deter-mined in cells transfected to express human norepinephrine transporter (NET), serotonin transporter (SERT), and dopamine transporter (DAT) via competition binding assays. All compounds studied in this series exhibit a moderate to high potency at all three transporters with SERT or DAT selectivity. 3 beta-(4'-iodo)phenyltropane bearing methylene on the bridge to the 2 beta-position (24) presents a particularly attractive pharmacological profile, with very high SERT affinity (K-i = 0.09 nM) and selectivity versus NET (65-fold) and DAT (94-fold). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.098
• 作为产物：
  描述：

  methyl 8-methyl-3-oxo-8-azabicyclo<3.2.1>octan-2-carboxylate 在 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 1-氯乙基氯甲酸酯 、 乙酸酐 、 magnesium 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 Nor-CBT
  参考文献：
  名称：

  [EN] METHOD FOR THE PREPARATION OF N-MONOFLUOROALKYL TROPANES AND THEIR USE
  [FR] PROCÉDÉ DE PRÉPARATION DE N-MONOFLUOROALKYL-TROPANES ET LEUR UTILISATION

  摘要：

  本发明涉及一种制备N-单氟烷基曲巴克碱的方法，一种制备三烷基锡曲巴克碱的方法，一种制备碘化和/或放射碘化曲巴克碱的方法，以及将N-单氟烷基曲巴克碱用作三烷基锡曲巴克碱和/或碘化和/或放射碘化曲巴克碱制备方法中的前体的用途。

  公开号：

  WO2021148598A1

文献信息

• Synthesis, Radiosynthesis, and Biological Evaluation of Carbon-11 and Fluorine-18 (<i>N</i>-Fluoroalkyl) Labeled 2β-Carbomethoxy-3β-(4'-(3-furyl)phenyl)tropanes and -nortropanes:  Candidate Radioligands for in Vivo Imaging of the Serotonin Transporter with Positron Emission Tomography
  作者：Jeffrey S. Stehouwer、Christophe Plisson、Nachwa Jarkas、Fanxing Zeng、Ronald J. Voll、Larry Williams、Laurent Martarello、John R. Votaw、Gilles Tamagnan、Mark M. Goodman

  DOI：10.1021/jm0504095

  日期：2005.11.1

  N-fluorobutyl (5) derivatives. The binding affinity for each compound to the human serotonin, dopamine, and norepinephrine transporters was determined using transfected HEK-293 cells. Radiolabeling and microPET brain imaging studies were performed with [(11)C]1, [(11)C]2, and [(18)F]3 to determine their utility as in vivo imaging agents.

  与N-甲基（2），N-氟乙基（3），N-氟丙基（4）和N-氟丁基（5）衍生物。使用转染的HEK-293细胞确定每种化合物对人血清素，多巴胺和去甲肾上腺素转运蛋白的结合亲和力。用[（11）C] 1，[（11）C] 2和[（18）F] 3进行了放射性标记和microPET脑成像研究，以确定它们作为体内成像剂的效用。
• Synthesis and biological evaluation of a series of novel N- or O-fluoroalkyl derivatives of tropane: potential positron emission tomography (PET) imaging agents for the dopamine transporter
  作者：Xiao-Hui Gu、Rushi Zong、Nora S Kula、Ross J Baldessarini、John L Neumeyer

  DOI：10.1016/s0960-894x(01)00626-6

  日期：2001.12

  fluoroalkyl-containing tropane derivatives was synthesized, and their binding affinities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) were determined via competitive binding assays. Among these derivatives, the fluoropropyl ester of beta-CIT (19), the fluoroethyl ester of beta-CIT (20), the N-fluoropropyl derivative of beta-CBT (12), and the fluoropropyl

  合成了一系列新颖的含氟烷基的托烷衍生物，并通过竞争性结合试验确定了它们与多巴胺转运蛋白（DAT），5-羟色胺转运蛋白（SERT）和去甲肾上腺素转运蛋白（NET）的结合亲和力。在这些衍生物中，β-CIT的氟丙基酯（19），β-CIT的氟乙基酯（20），β-CBT的N-氟丙基衍生物（12）和β-CMT的氟丙基酯（18）与FP-CIT相比，DAT对SERT和NET具有更高的亲和力和更高的选择性，这表明它们对于DAT的（18）F标记PET显像剂的开发具有吸引力。
• 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, Radiosynthesis, and Biological Evaluation of Carbon-11 and Iodine-123 Labeled 2β-Carbomethoxy-3β-[4‘-((<i>Z</i>)-2-haloethenyl)phenyl]tropanes:  Candidate Radioligands for in Vivo Imaging of the Serotonin Transporter
  作者：Christophe Plisson、Jonathan McConathy、Laurent Martarello、Eugene. J. Malveaux、Vernon M. Camp、Larry Williams、John R. Votaw、Mark M. Goodman

  DOI：10.1021/jm030384e

  日期：2004.2.1

  2beta-Carbomethoxy-3beta-[4'-((Z)-2-iodoethenyl)phenyl]tropane (ZIET) and 2beta-carbomethoxy-3beta-[4'-((Z)-2-bromoethenyl)phenyl]tropane (ZBrET) were synthesized as well as their nortropane congeners ZIENT and ZBrENT. Binding affinities of these compounds were determined in cells transfected to express human SERT, DAT, and NET using [3H]citalopram, [125I]RTI-55, and [3H]nisoxetine, respectively. Both

  2beta-Carbomethoxy-3beta- [4'-（（（Z）-2-iodoethenyl）phenyl] tropane（ZIET）和2beta-carbomethoxy-3beta- [4'-（（（Z）-2-bromoethenyl] phenyl] tropane（ZBrET ）以及它们的正烷烃同系物ZIENT和ZBrENT。使用[3H]西酞普兰，[125I] RTI-55和[3H]尼西西汀分别测定转染表达人SERT，DAT和NET的细胞中这些化合物的结合亲和力。ZIET和ZBrET都显示出对SERT的高度亲和力（分别为Ki = 0.11和0.08 nM）。ZIET和ZBrET对DAT的亲和力分别比SERT低200倍和38倍。[11C] ZIET和[11C] ZBrET是通过用[11C]甲基碘将其相应的降冰片烷进行烷基化制备的，其放射化学收率约为30％（衰减校正至轰击结束，EOB）。高比活度[123I]
• 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：——