(R)-(+)-安那他品 | 126454-22-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (R)-(+)-安那他品
• 英文名称: (R)-1,2,3,6-tetrahydro-2,3'-bipyridine
• 英文别名: (R)-anatabine；R-anatabine；(R)-(+)-Anatabine；3-[(2R)-1,2,3,6-tetrahydropyridin-2-yl]pyridine
• CAS: 126454-22-6
• 化学式: C₁₀H₁₂N₂
• 分子量: 160.219
• InChiKey: SOPPBXUYQGUQHE-SNVBAGLBSA-N

物化性质

• 沸点：
  269.0±28.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

制备方法与用途

(R)-(+)-Anatabine 是一种低活性的 S 型异构体，属于 Anatabine 家族。这种化合物是一种有效的 α4β2 nAChR 激动剂。它通过阻止淀粉样蛋白前体蛋白的 β 裂解，抑制 NF-κB 的激活，并减少淀粉样 β (Aβ) 的生成。此外，Anatabine 还具有抗炎作用，在研究神经退行性疾病方面展现出潜力。

反应信息

• 作为反应物：
  描述：

  (R)-(+)-安那他品 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以76%的产率得到+-八角枫碱
  参考文献：
  名称：

  双功能高烯丙胺的合成修饰：2-芳基哌啶、(R)-anatabine 和 (R)-anabasine 的合成

  摘要：

  摘要 具有正交双功能手柄、胺和侧链烯丙基单元的手性高烯丙基胺可以很容易地转化为 N-杂环。N-烯丙基化和 Ru 催化的闭环复分解分三步提供具有生物活性的 2-芳基哌啶、烟草生物碱 (R)-anatabine 和 (R)-anabasine。(R)-N-methylanatabine 和 (R)-N-methylanabasine 的正式合成也已完成。图形概要

  DOI：

  10.1080/00397911.2019.1643890
• 作为产物：
  描述：

  氯化-1-(2,4-二硝基苯基)吡啶嗡盐 在 sodium hydroxide 、 sodium tetrahydroborate 、 草酰氯 、 TEA 、 二甲基亚砜 、 2,4-二硝基苯肼 作用下， 以 丙醇 、 乙醚 、 溶剂黄146 、 正丁醇 为溶剂， 反应 48.17h， 生成 (R)-(+)-安那他品
  参考文献：
  名称：

  Genisson, Yves; Mehmandoust, Maryam; Marazano, Christian, Heterocycles, 1994, vol. 39, # 2, p. 811 - 818

  摘要：

  DOI：

文献信息

• A stereoselective route to enantiomeric 2-alkyl-1,2,3,6-tetrahydropyridines
  作者：Maryam Mehmandoust、Christian Marazano、Bhupesh C. Das

  DOI：10.1039/c39890001185

  日期：——

  A synthesis of (R)- or (S)-2-alkyl-1,2,3,6-tetrahydropyridines (1), starting from (R)- or(S)-phenylglycinol and Zincke's salt (2), and proceeding via the new oxazolidine derivative (5) as a key intermediate, is described.

  （R）-或（S）-2-烷基-1,2,3,6-四氢吡啶（1）的合成，从（R）-或（S）-苯基甘氨醇和辛克盐（2）开始进行描述了通过新的恶唑烷衍生物（5）作为关键中间体。
• USE OF ANATABINE TO TREAT INFLAMMATION AND METHODS OF SYNTHESIZING ANATABINE
  申请人：Philip Morris Products S.A.

  公开号：EP3524246A1

  公开（公告）日：2019-08-14

  There is disclosed herein anatabine adipate and compositions and uses thereof.

  本文公开了己二酸阿纳他滨及其组合物和用途。
• Asymmetric synthesis of functionalized piperidine derivatives: synthesis of (S)-anatabine
  作者：Thiagarajan Balasubramanian、Alfred Hassner

  DOI：10.1016/s0957-4166(98)00225-0

  日期：1998.7

  A short and efficient chiral synthesis of 6-aryl-5-phenylsulfonyl-1,2,5,6-tetrahydropyridines was achieved in moderate yield and with good selectivity. The absolute configurations were assigned by extending the methodology to (S)-anatabine and as well with NMR experiments. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereoselectivity of the demethylation of nicotine piperidine homologues by Nicotiana plumbaginifolia cell suspension cultures
  作者：Trixie Ann Bartholomeusz、Roland Molinié、Albrecht Roscher、François-Xavier Felpin、Françoise Gillet、Jacques Lebreton、François Mesnard、Richard J. Robins

  DOI：10.1016/j.phytochem.2005.07.012

  日期：2005.8

  The metabolism of (R,S)-N-methylanabasine and (R,S)-N-methylanatabine has been studied in a cell suspension culture of Nicotiana plumbaginifolia. Both substrates are effectively demethylated, anabasine or anatabine, respectively, accumulating in the medium. Similarly, there is strong stereoselectivity for the (R)-isomers of both substrates. The kinetics of metabolism of (R,S)-N-methylanabasine differ significantly from those of nicotine in that no further degradation of the initial demethylation product occurs. (R,S)-N-Methylanatabine, however, shows kinetics closer to those of nicotine, with loss of alkaloid from the system. Furthermore, (R,S)-N-methylanabasine does not diminish (S)-nicotine demethylation, indicating a lack of competition. However, the metabolism of (S)-nicotine is affected by the presence of (R,S)-N-methylanabasine. Hence, the demethylation of the piperidine homologues of nicotine is seen to be similar but not identical to that of the pyridine analogues. The implications of these different metabolic profiles in relation to the demethylation activity are discussed. (c) 2005 Elsevier Ltd. All rights reserved.
• METHODS AND PRODUCTS FOR TREATING INFLAMMATION
  申请人：Williams Jonnie R.

  公开号：US20120196899A1

  公开（公告）日：2012-08-02

  Pharmaceutical compositions comprising an isolated form of a compound of Formula IB (e.g., R-(+)-anatabine) or a salt thereof can be used to treat disorders comprising an inflammatory component, including chronic, low-level inflammation. Compounds of Formula I also can be provided, for example, in other vehicles such as beverage products and consumer products such as lotions and creams.