去甲塞利吉林 | 18913-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 去甲塞利吉林
• 英文名称: nordeprenyl
• 英文别名: N-desmethylselegiline；desmethylselegiline；N-(1-phenylpropan-2-yl)prop-2-yn-1-amine；selegiline；rac-N-propargylamphetamine；desmethyl-selegilin；1-phenyl-N-prop-2-ynylpropan-2-amine
• CAS: 18913-84-3
• 化学式: C₁₂H₁₅N
• mdl: MFCD17274354
• 分子量: 173.258
• InChiKey: UUFAJPMQSFXDFR-UHFFFAOYSA-N

物化性质

• 沸点：
  275.3±15.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)
• 闪点：
  9℃
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）、甲醇（少量）
• 保留指数：
  1362.8

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 储存条件：
  -20°C冷冻保存，在惰性气体氛围下

制备方法与用途

诺雷德林是去甲阿朴菲的代谢产物。去甲阿朴菲是一种强效、选择性且不可逆的MAO-B抑制剂。

反应信息

• 作为反应物：
  描述：

  去甲塞利吉林 生成 N-(111C)methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
  参考文献：
  名称：

  HALLDIN C.; FOWLER J.; BJURLING P.; MACGREGOR R.; ARNETT C.; WOLF A.; LAN+, J. LABELLED COMPOUNDS AND RADIOPHARM., 23,(1986) N 10-12, 1400-1402

  摘要：

  DOI：
• 作为产物：
  描述：

  烯丙苯 在 盐酸 、 双(乙腈)氯化钯(II) 、 sodium cyanoborohydride 、 potassium carbonate 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 56.0h， 生成 去甲塞利吉林
  参考文献：
  名称：

  烯丙基（杂）芳烃的 Markovnikov Wacker-Tsuji 氧化及其在对映体富集胺和醇的一锅光金属生物催化方法中的应用

  摘要：

  介绍了在光催化条件下各种烯丙基（杂）芳烃的 Wacker-Tsuji 有氧氧化形成相应的甲基酮。通过使用钯络合物 [PdCl 2 (MeCN) 2 ] 和光敏剂 [Acr-Mes]ClO 4在水性介质中和室温下，通过简单的蓝色 LED 光照射，以高转化率 (>80%) 和优异的选择性 (>90%) 合成了所需的羰基化合物。关键过程是可以激活氧气的 Pd 纳米粒子的瞬时形成，从而回收瓦克氧化反应中所需的 Pd(II) 物质。虽然光照射是严格强制性的，但光催化剂的加入提高了反应选择性，因为从一些获得的副产物中形成起始烯丙基（杂）芳烃，从而回到瓦克-辻催化循环。优化后，将氧化反应与酶促转化结合在一锅两步顺序方案中。取决于所使用的生物催化剂，i．e.R )- 和 ( S )-1-arylpropan-2-amines 或 1-arylpropan-2-ols 在大多数情况下可以以高产率 (>70%)

  DOI：

  10.1002/adsc.202100351

文献信息

• COMPOUNDS FOR USE IN IMAGING, DIAGNOSING AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM OR OF TUMORS
  申请人：Lehmann Lutz

  公开号：US20100233086A1

  公开（公告）日：2010-09-16

  This invention relates to novel compounds suitable for labelling or already labelled by 18 F, methods of preparing such a compound, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by positron emission tomography (PET).

  本发明涉及适用于标记或已经通过18F标记的新型化合物，制备这种化合物的方法，包含这种化合物的组合物，包含这种化合物或组合物的试剂盒以及这种化合物，组合物或试剂盒用于正电子发射断层摄影（PET）的诊断成像的用途。
• Compounds for use in imaging, diagnosing and/or treatment of diseases of the central nervous system or of tumors
  申请人：Lehmann Lutz

  公开号：US08784775B2

  公开（公告）日：2014-07-22

  This invention relates to novel compounds suitable for labeling or already labeled by 18F, methods of preparing such a compound, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by positron emission tomography (PET).

  本发明涉及一种新型化合物，适用于标记或已经用18F标记，制备此类化合物的方法，包含此类化合物的组合物，包含此类化合物或组合物的工具箱以及此类化合物、组合物或工具箱用于正电子发射断层摄影（PET）诊断成像的用途。
• FMO3 inhibitors for treating pain
  申请人：Akron Molecules GmbH

  公开号：EP2674161A1

  公开（公告）日：2013-12-18

  The present invention relates to new therapies to treat pain and related diseases, as well as pharmaceutical compounds for use in said therapies.

  本发明涉及治疗疼痛和相关疾病的新疗法，以及用于上述疗法的药物化合物。
• Chemoenzymatic Synthesis of Selegiline: An Imine Reductase-Catalyzed Approach
  作者：Yuliang Hu、Jinping Bao、Dongyu Tang、Shushan Gao、Fei Wang、Zhongtao Ding、Chengsen Cui

  DOI：10.3390/molecules29061328

  日期：——

  drug indicated for the treatment of early-stage Parkinson’s disease. Herein, we report a new short chemoenzymatic approach (in 2 steps) towards the synthesis of (R)-selegiline via stereoselective biocatalytic reductive amination as the key step. The imine reductase IR36-M5 mutant showed high conversion (97%) and stereoselectivity (97%) toward the phenylacetone and propargyl amine substrates, offering

  (R)-同苄胺是 (R)-司来吉兰（一种用于治疗早期帕金森病的药物）中存在的关键结构基序。在此，我们报告了一种新的短化学酶方法（分两步）通过立体选择性生物催化还原胺化作为关键步骤来合成（R）-司来吉兰。亚胺还原酶IR36-M5突变体对苯丙酮和炔丙胺底物表现出高转化率(97%)和立体选择性(97%)，为合成烷基化高苄胺提供了有价值的生物催化剂。
• Metabolism of N,N-dialkylated amphetamines, including deprenyl, by CYP2D6 expressed in a human cell line
  作者：M. V. Bach、R. T. Coutts、G. B. Baker

  DOI：10.1080/004982500237686

  日期：2000.1

  1. Five N,N-dialkylated amphetamines, N-methyl-N-propargylamphetamine (deprenyl; DEP), N-benzyl-N-methylamphetamine (benzphetamine; BPA), N-allyl-N-methylamphetamine (AMA), N,N-diallylamphetamine (DAA) and N-methyl-N-propylamphetamine (MPA), were metabolized in vitro with a microsomal preparation from cells expressing human CYP2D6 to determine what influence the N,N-dialkyl substituents had on the extent of N-dealkylation and/or aromatic ring oxidation.2. The results obtained from experiments with the first two substrates, DEP and BPA, were surprisingly different. Whereas DEP was N-demethylated and N-depropargylated by the CYP2D6 enzyme system, no metabolites were formed from BPA. Subsequently, it was determined that AMA, DAA and MPA also underwent CYP2D6-catalysed N-dealkylation. Both N-methyl- and N-allylamphetamine were identified as products of AMA metabolism; similarly, metabolism of MPA produced both N-methyl- and N-propargylamphetamine, and N-allylamphetamine was the sole metabolite of DAA.3. No N,N-didealkylated product (i.e. amphetamine) was isolated from incubates of any of the five substrates, and none of the N,N-dialkylated substrates was metabolized to a ring-hydroxylated product.4. Rates of these CYP2D6-catalysed reactions were dependent on the nature and degree of unsaturation of the N-substituents.