1-methyl-4-(3-pyridinyl)-1,2,5,6-tetrahydropyridine | 90606-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-methyl-4-(3-pyridinyl)-1,2,5,6-tetrahydropyridine
• 英文别名: 1-methyl-4-(3'-pyridyl)-1,2,5,6-tetrahydropyridine；1''-Methyl-1'',2'',3'',6''-tetrahydro-[3,4'']bipyridinyl；3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)pyridine
• CAS: 90606-89-6
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: AHHWWZNACRZOOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(3-pyridinyl)-1,2,5,6-tetrahydropyridine 在 sodium phosphate buffer 、 monoamine oxidase-B 作用下， 生成 1-methyl-4-(3-pyridyl)-1,2-dihydropyridinium
  参考文献：
  名称：

  Studies on the Monoamine Oxidase-B-Catalyzed Biotransformation of 4-Azaaryl-1-methyl-1,2,3,6-tetrahydropyridine Derivatives

  摘要：

  The substrate properties of a series of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinyl (MPTP) analogues in which the C-4 phenyl group has been replaced with various 4-azaaryl moieties have been examined in an effort to evaluate the contribution of electronic, polar, and steric parameters to the MAO-B-catalyzed oxidation of this type of cyclic tertiary allylamine to the corresponding dihydropyridinium metabolite. No significant correlation could be found nit-h the calculated energy of the C-H bond undergoing cleavage. A general trend, however, was observed between the magnitude of the log P value with the magnitude of k(cat)/K-m. The results indicate that the placement of a polar nitrogen atom in the space occupied by the phenyl group of MPTP leads to a dramatic decrease in substrate properties. Enhanced substrate properties, however, were observed when benzoazaarenes replaced the corresponding five-membered azaarenes. These results are consistent with our previously published molecular model of the active site of MAO-B.

  DOI：

  10.1021/jm9900319
• 作为产物：
  描述：

  3-pyridyllithium 在 正丁基锂 、 硫酸 作用下， 反应 5.5h， 生成 1-methyl-4-(3-pyridinyl)-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Adrenoceptor and tetrabenazine antagonism activities of some pyridinyltetrahydropyridines

  摘要：

  A series of pyridinyltetrahydropyridine derivatives was synthesized and evaluated as adrenoceptor and tetrabenazine antagonists. 4-(3-Fluoro-2-pyridinyl)-1,2,5,6-tetrahydropyridine proved to be the most potent and selective alpha 2-adrenoceptor antagonist of the series as measured in vitro by displacement of [3H]clonidine and [3H]prazosin from membrane binding sites of calf cerebral cortex and by antagonism of the effects of clonidine and methoxamine in the rat isolated, field-stimulated vas deferens. In addition, this compound, and the corresponding desfluoro derivative, blocked tetrabenazine-induced ptosis in the mouse.

  DOI：

  10.1021/jm00375a017

文献信息

• Pyrazolopyrimidines, a process for their preparation and their use as medicine
  申请人：Danysz Wojciech

  公开号：US20080032998A1

  公开（公告）日：2008-02-07

  Substituted pyrazolopyrimidine derivatives of formula (I) wherein R 1 represents chloro or bromo; R 2 , R 3 , R 4 , R 5 , R 6 and R 7 independently represent e.g. hydrogen or C 1-6 -alkyl; R 8 represents a radical R 9 or a radical R 10 , whereby one of the two radicals R 8 represents R 9 and the other radical R 8 represents Ret; R 9 represents e.g. a phenyl or thiophene group, and R 10 represents e.g. hydrogen or methyl; are potent mGluR5 modulators and are useful for the prevention of acute and chronic neurological disorders.

  取代吡唑并嘧啶衍生物的公式(I) 其中 R1代表氯或溴； R2、R3、R4、R5、R6和R7独立代表例如氢或C1-6-烷基； R8代表R9的基团或R10的基团，其中两个R8基团之一代表R9，另一个R8基团代表Ret；R9代表例如苯基或噻吩基团，R10代表例如氢或甲基； 是有效的mGluR5调节剂，可用于预防急性和慢性神经障碍。
• 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。
• Structure−Affinity Relationships of a Unique Nicotinic Ligand:  N-Dimethyl-N⁴-phenylpiperazinium Iodide (DMPP)
  作者：Maria Novella Romanelli、Dina Manetti、Serena Scapecchi、Pier Andrea Borea、Silvia Dei、Alessandro Bartolini、Carla Ghelardini、Fulvio Gualtieri、Luca Guandalini、Katia Varani

  DOI：10.1021/jm010901y

  日期：2001.11.1

  DMPP is a well-known nicotinic agonist that does not fit any proposed pharmacophore for nicotinic binding and represents a unique ligand among the hundreds of nicotinic agonists studied in the past decades. A systematic modulation of the chemical structure of DMPP, aimed to establish its structure-affinity relationships, is reported. The research has allowed to identify molecules such as I Ic, 13c, 14c, and 28c, with affinities for alpha (4)beta (2) receptors in the low nanomolar range, some 2 orders of magnitude lower than the lead compound. The agonistic properties of the most interesting compounds have been assessed by measuring their analgesic activity on mice (hot-plate test). Another result of the research was the identification of DMPP analogues, such as 3a (K-i = 90 nM) and 14b (K-i = 180 nM), that maintain affinity for the central nicotinic receptor when the ammonium function is changed into an aminic one and are therefore possible leads for drug development in neurodegenerative diseases.
• Studies on the Monoamine Oxidase-B-Catalyzed Biotransformation of 4-Azaaryl-1-methyl-1,2,3,6-tetrahydropyridine Derivatives
  作者：Sandeep K. Nimkar、Stéphane Mabic、Andrea H. Anderson、Sonya L. Palmer、Thomas H. Graham、Milly de Jonge、Lisa Hazelwood、Sean J. Hislop、Neal Castagnoli

  DOI：10.1021/jm9900319

  日期：1999.5.1

  The substrate properties of a series of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinyl (MPTP) analogues in which the C-4 phenyl group has been replaced with various 4-azaaryl moieties have been examined in an effort to evaluate the contribution of electronic, polar, and steric parameters to the MAO-B-catalyzed oxidation of this type of cyclic tertiary allylamine to the corresponding dihydropyridinium metabolite. No significant correlation could be found nit-h the calculated energy of the C-H bond undergoing cleavage. A general trend, however, was observed between the magnitude of the log P value with the magnitude of k(cat)/K-m. The results indicate that the placement of a polar nitrogen atom in the space occupied by the phenyl group of MPTP leads to a dramatic decrease in substrate properties. Enhanced substrate properties, however, were observed when benzoazaarenes replaced the corresponding five-membered azaarenes. These results are consistent with our previously published molecular model of the active site of MAO-B.
• Adrenoceptor and tetrabenazine antagonism activities of some pyridinyltetrahydropyridines
  作者：Walfred S. Saari、Wasyl Halczenko、Joel R. Huff、James P. Guare、Cecilia A. Hunt、William C. Randall、Victor J. Lotti、George G. Yarbrough

  DOI：10.1021/jm00375a017

  日期：1984.9

  A series of pyridinyltetrahydropyridine derivatives was synthesized and evaluated as adrenoceptor and tetrabenazine antagonists. 4-(3-Fluoro-2-pyridinyl)-1,2,5,6-tetrahydropyridine proved to be the most potent and selective alpha 2-adrenoceptor antagonist of the series as measured in vitro by displacement of [3H]clonidine and [3H]prazosin from membrane binding sites of calf cerebral cortex and by antagonism of the effects of clonidine and methoxamine in the rat isolated, field-stimulated vas deferens. In addition, this compound, and the corresponding desfluoro derivative, blocked tetrabenazine-induced ptosis in the mouse.