1-methyl-3-phenyl-3-pyrroline | 97382-80-4

• 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: 1-methyl-3-phenyl-3-pyrroline
• 英文别名: 1-Methyl-3-phenyl-2,5-dihydropyrrole
• CAS: 97382-80-4
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: YSXZLMAVUKNKOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-3-phenyl-3-pyrroline 在 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以71%的产率得到1-methyl-3-phenylpyrrolidine
  参考文献：
  名称：

  Interactions of 1-methyl-3-phenylpyrrolidine and 3-methyl-1-phenyl-3-azabicyclo[3.1.0]hexane with monoamine oxidase B

  摘要：

  The parkinsonian inducing agent 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and its corresponding five-membered ring analogue 1-methyl-3-phenyl-3-pyrroline are cyclic tertiary allyl-amines and good substrates of monoamine oxidase B (MAO-B). The MAO-B catalyzed 2-electron alpha-carbon oxidation of this class of substrates appears to be dependent on the presence of the allylic pi-bond since the corresponding saturated piperidinyl analogue of MPTP is reported not to be an MAO-B substrate. The only saturated cyclic tertiary amine known to act as an MAO-B substrate is the 3,4-cyclopropyl analogue of MPTP, 3-methyl-6-phenyl-3-azabicyclo[4.1.0]heptane. As part of our ongoing studies we have examined the MAO-B substrate properties of the corresponding pyrrolidinyl analogue, 1-methyl-3-phenylpyrrolidine, and the 3,4-cyclopropyl analogue, 3-methyl-1-phenyl-3-azabicyclo[3.1.0]hexane. The results document that both the pyrrolidinyl analogue [K-m = 234 mu M; V-max = 8.37 nmol/(min-mg mitochondrial protein)] and the 3,4-cyclopropyl analogue [K-m = 148 mu M; V-max = 16.9 nmol/(min-mg mitochondrial protein)] are substrates of baboon liver mitochondrial MAO-B. We also have compared the neurotoxic potential of these compounds in the C57BL/6 mouse. The results led us to conclude that these compounds are not MPTP-type neurotoxins. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.079
• 作为产物：
  描述：

  3-苯基吡咯烷-3-醇 在 sodium carbonate 作用下， 反应 3.0h， 生成 1-methyl-3-phenyl-3-pyrroline
  参考文献：
  名称：

  Neurotoxicity studies with the monoamine oxidase B substrate 1-methyl-3-phenyl-3-pyrroline

  摘要：

  The neurotoxic properties of the parkinsonian inducing agent 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) are dependent on its metabolic activation in a reaction catalyzed by centrally located monoamine oxidase B (MAO-13). This reaction ultimately leads to the permanently charged 1-methyl-4-phenylpyridinium species MW, a 4-electron oxidation product of MPTP and a potent mitochondrial toxin. The corresponding 5-membered analogue, 1-methyl-3-phenyt-3-pyrroline, is also a selective MAO-13 substrate. Unlike MPTP, the MAO-B-catalyzed oxidation of 1-methyl-3-phenyl-3-pyrroline is a 2-electron process that leads to the neutral 1-methyl-3-phenylpyrrole. MPP+ is thought to exert its toxic effects only after accumulating in the mitochondria, a process driven by the transmembrane electrochemical gradient. Since this energy-dependent accumulation of MPP+ relies upon its permanent charge, 1-methyl-3-phenyl-3-pyrrolines and their pyrrolyl oxidation products should not be neurotoxic. We have tested this hypothesis by examining the neurotoxic potential of 1-methyl-3-phenyl-3-pyrroline and 1-methyl-3-(4chlorophenyl)-3-pyrroline in the C57BL/6 mouse model. These pyrrolines did not deplete striatal dopamine while analogous treatment with MPTP resulted in 65-73% depletion. Kinetic studies revealed that both 1-methyl-3-phenyl-3-pyrroline and its pyrrolyl oxidation product were present in the brain in relatively high concentrations. Unlike MPP+, however, 1-methyl-3-phenylpyrrole was cleared from the brain quickly. These results suggest that the brain MAO-B-catalyzed oxidation of xenobiotic amines is not, in itself, sufficient to account for the neurodegenerative properties of a compound like MPTP. The rapid clearance of 1-methyl-3-phenylpyrroles from the brain may contribute to their lack of neurotoxicity. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2007.06.014

文献信息

• 1-Methyl-3-pyrrolines and 2-methylisoindolines: new classes of cyclic tertiary amine monoamine oxidase B substrates
  作者：You-Xiong Wang、Stéphane Mabic、Neal Castagnoli Jr

  DOI：10.1016/s0968-0896(97)10020-7

  日期：1998.2

  Both 1-methyl-3-pyrrolines and 2-methylisoindolines are substrates for MAO-B with Vmax/Km values ranging from 200 to 2000 min-1 mM-1 at 37 degrees C. These compounds represent new classes of cyclic tertiary amine substrates for this flavoenzyme. The only other known cyclic amines that are MAO-B substrates are 1,4-disubstituted 1,2,3,6-tetrahydropyridinyl derivatives. The presence of an allylic (benzylic)

  1-甲基-3-吡咯啉和2-甲基异吲哚啉均是MAO-B的底物，在37摄氏度时Vmax / Km值在200至2000 min-1 mM-1范围内。这些化合物代表了新型的环状叔胺底物这种黄素酶。作为MAO-B底物的唯一其他已知的环状胺是1,4-二取代的1,2,3,6-四氢吡啶基衍生物。所有这些化合物中烯丙基（苄基）氨基官能团的存在都可能与其底物性质有关，因为相关的哌啶基和吡咯烷基类似物在MAO-B的存在下是稳定的。本文讨论了这些化合物的能量和几何特征，与它们的底物性质有关，并预期了它们可用于探测该黄酮酶的活性位点。
• THERAPEUTIC AGENT FOR TAUOPATHIES
  申请人：Sumitomo Pharma Co., Ltd.

  公开号：EP4104861A1

  公开（公告）日：2022-12-21

  The present invention is to provide a medicament for treating and/or preventing tauopathy by activating the voltage-gated sodium channel (Nav). The present invention relates to a medicament for treating and/or preventing tauopathy, comprising a Nav activator as an active ingredient.

  本发明提供了一种通过激活电压门控钠通道（Nav）治疗和/或预防tau病的药物。本发明涉及一种治疗和/或预防tau病的药物，其包括Nav激活剂作为活性成分。
• Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles
  作者：Nicoló Scalacci、Gary W. Black、Giulio Mattedi、Nicola L. Brown、Nicholas J. Turner、Daniele Castagnolo

  DOI：10.1021/acscatal.6b03081

  日期：2017.2.3

  A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis aromatization sequence.
• SATZINGER, G.;MANNHARDT, K.;HARTENSTEIN, J.;HERRMANN, M.;FRITSCHL, E.;STE+
  作者：SATZINGER, G.、MANNHARDT, K.、HARTENSTEIN, J.、HERRMANN, M.、FRITSCHL, E.、STE+

  DOI：——

  日期：——
• 3-Aryl-3-pyrrolin-Derivate, Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel für die Bekämpfung von Herz- und Gefässkrankheiten
  申请人：GÖDECKE AKTIENGESELLSCHAFT

  公开号：EP0133578B1

  公开（公告）日：1990-08-01