(1S,2R)-2-(methyl(prop-2-ynyl)amino)-1-phenylpropan-1-ol | 1146971-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-2-(methyl(prop-2-ynyl)amino)-1-phenylpropan-1-ol
• 英文别名: (1S,2R)-2-(Methyl-prop-2-ynyl-amino)-1-phenyl-propan-1-ol；(1S,2R)-2-[methyl(prop-2-ynyl)amino]-1-phenylpropan-1-ol
• CAS: 1146971-56-3
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: ALYVCRJVPZAKEO-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-(methyl(prop-2-ynyl)amino)-1-phenylpropan-1-ol 在 potassium [¹⁸F]fluoride 、 甲基磺酰氯 、 三乙胺 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.33h， 生成 N-[(1S,2R)-1-[18F]fluoro-1-phenylpropan-2-yl]-N-methylprop-2-yn-1-amine
  参考文献：
  名称：

  Synthesis of Three Novel Fluorine-18 Labeled Analogues of l-Deprenyl for Positron Emission Tomography (PET) studies of Monoamine Oxidase B (MAO-B)

  摘要：

  The aim in this project was to synthesize and to study fluorine-18 labeled analogues of L-deprenyl which bind selectively to the enzyme monoamine oxidase B (MAO-B). Three fluorinated L-deprenyl analogues have been generated in multistep organic syntheses. The most promising fluorine-18 compound N-[(2S)-1-[F-18]fluoro-3-phenylpropan-2-yl]-N-methylprop-2-yn-1-amine (4c) was synthesized by a one-step fluorine-18 nucleophilic substitution reaction. Autoradiography on human brain tissue sections demonstrated specific binding for compound 4c to brain regions known to have a high content of MAO-B. In addition, the corresponding nonradioactive fluorine-19 compound (13) inhibited recombinant human MAO-B with an IC50 of 170.5 +/- 29 n/v1 but did not inhibit recombinant human MAO-A (IC50 > 2000 nM), demonstrating its specificity. Biodistribution of 4c in mice showed high initial brain uptake leveling at 5.4 +/- 0.04%ID/g after 2 min post injection. In conclusion, compound 4c is a specific inhibitor of MAO-B with high initial brain uptake in mice and is, therefore, a candidate for further investigation in PET.

  DOI：

  10.1021/jm200710b
• 作为产物：
  描述：

  (4R,5S)-(+)-4-甲基-5-苯基-2-恶唑啉酮 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2R)-2-(methyl(prop-2-ynyl)amino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  Synthesis of Three Novel Fluorine-18 Labeled Analogues of l-Deprenyl for Positron Emission Tomography (PET) studies of Monoamine Oxidase B (MAO-B)

  摘要：

  The aim in this project was to synthesize and to study fluorine-18 labeled analogues of L-deprenyl which bind selectively to the enzyme monoamine oxidase B (MAO-B). Three fluorinated L-deprenyl analogues have been generated in multistep organic syntheses. The most promising fluorine-18 compound N-[(2S)-1-[F-18]fluoro-3-phenylpropan-2-yl]-N-methylprop-2-yn-1-amine (4c) was synthesized by a one-step fluorine-18 nucleophilic substitution reaction. Autoradiography on human brain tissue sections demonstrated specific binding for compound 4c to brain regions known to have a high content of MAO-B. In addition, the corresponding nonradioactive fluorine-19 compound (13) inhibited recombinant human MAO-B with an IC50 of 170.5 +/- 29 n/v1 but did not inhibit recombinant human MAO-A (IC50 > 2000 nM), demonstrating its specificity. Biodistribution of 4c in mice showed high initial brain uptake leveling at 5.4 +/- 0.04%ID/g after 2 min post injection. In conclusion, compound 4c is a specific inhibitor of MAO-B with high initial brain uptake in mice and is, therefore, a candidate for further investigation in PET.

  DOI：

  10.1021/jm200710b

文献信息

• Synthesis of novel 1,4-disubstituted 1,2,3-triazolo-bosentan derivatives – evaluation of antimicrobial and anticancer activities and molecular docking
  作者：K. Easwaramoorthi、A. Jeya Rajendran、K. Chennakesava Rao、Y. Arun、C. Balachandran、P. T. Perumal、Nobuhiko Emi、S. M. Mahalingam、V. Duraipandiyan、N. A. Al-Dhabi

  DOI：10.1039/c5ra18618h

  日期：——

  Novel 1,4-disubstituted 1,2,3-triazolo bosentan derivatives 1a–n from bosentan 2 were synthesized in good yields by sequential chlorination, azidation followed by Cu(I) catalyzed 1,3-dipolar cycloaddition. All obtained compounds 1a–n were evaluated for their antimicrobial and in vitro anticancer activities and by in silico docking studies. Among all tested compounds 1e,f and 1h–j show better antimicrobial

  通过连续氯化，叠氮化，然后由Cu（I）催化1,3-偶极环加成反应，以高收率合成了来自波森坦2的新型1,4-二取代1,2,3-三唑并波生坦衍生物1a–n。通过计算机对接研究评估了所有获得的化合物1a–n的抗微生物和体外抗癌活性。在所有被测化合物1e，f和1h–j中，对被测细菌和真菌显示出更好的抗菌活性。进行抗癌测试时，化合物1g–j和1n对A549和SKOV-3细胞系均显示出显着活性，其IC 50值为7.81μgmL -1，其中化合物1i表现出非常强的活性。另外，在Vero细胞中没有计算出高达2 mg mL -1的毒性。在计算机上进行了研究，以研究1a–n与目标受体DNA拓扑异构酶IV（4 EMV）和间变性淋巴瘤激酶（2XP2）的可能结合方式。其中，化合物1e和1h分别显示与4EMV和2XP2受体的最大结合能，它们还具有良好的抗菌和有效的抗癌活性。
• 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。
• Compounds for use in imaging, diagnosing and/or treatment of diseases of the central nervous system or of tumors
  申请人：Bayer Schering Pharma AG

  公开号：EP2053033A1

  公开（公告）日：2009-04-29

  This invention relates to novel compounds suitable for labelling or already labelled 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).

  本发明涉及适合标记或已经标记 18F 的新型化合物、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试剂盒以及此类化合物、组合物或试剂盒在正电子发射断层扫描（PET）诊断成像中的用途。
• [EN] COMPOUNDS FOR USE IN IMAGING, DIAGNOSING, AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM OR OF TUMORS<br/>[FR] COMPOSÉS DESTINÉS À ÊTRE UTILISÉS DANS LE CADRE D'IMAGERIE, DE DIAGNOSTIC ET/OU DE TRAITEMENT DE MALADIES DU SYSTÈME NERVEUX CENTRAL OU DE TUMEURS
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2009052970A3

  公开（公告）日：2009-07-02