(+)-((2R,3S)-1-methyl-2-(pyridin-3-yl)pyrrolidin-3-yl)methanamine | 623579-03-3

• 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: (+)-((2R,3S)-1-methyl-2-(pyridin-3-yl)pyrrolidin-3-yl)methanamine
• 英文别名: ((2R,3S)-1-methyl-2-(pyridine-3-yl)pyrrolidin-3-yl)methanamine；rac-trans 3'-Aminomethyl Nicotine；[(2R,3S)-1-methyl-2-pyridin-3-ylpyrrolidin-3-yl]methanamine
• CAS: 623579-03-3
• 化学式: C₁₁H₁₇N₃
• mdl: MFCD20760322
• 分子量: 191.276
• InChiKey: IUMCSWXAFXSTAI-GXSJLCMTSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (±)-trans-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxamide 在 红铝 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以19%的产率得到(+)-((2R,3S)-1-methyl-2-(pyridin-3-yl)pyrrolidin-3-yl)methanamine
  参考文献：
  名称：

  A Conjugate Vaccine Using Enantiopure Hapten Imparts Superior Nicotine-Binding Capacity

  摘要：

  A leading nicotine conjugate vaccine was only efficacious for one-third of clinical trial participants, likely due in part to its use of racemic nicotine hapten, (+/-)-3'-AmNic. Immunization of male Wistar rats with (+)-, (-)-, or (+/-)-3'-AmNicSucTT and subsequent antibody immunoassays suggest that a vaccine using enantiopure (-)-3'-AmNic hapten imparts superior capacity to bind (-)-nicotine. Future nicotine vaccine clinical candidates must incorporate this design consideration (i.e., hapten enantiopurity) in order to maximize efficacy.

  DOI：

  10.1021/jm501625j

文献信息

• [EN] ENANTIOPURE HAPTENS FOR NICOTINE VACCINE DEVELOPMENT<br/>[FR] HAPTÈNES ÉNANTIOPURS POUR DÉVELOPPER DES VACCINS CONTRE LA NICOTINE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2015179403A1

  公开（公告）日：2015-11-26

  The invention provides chiral haptens (-)-3'-AmNic and (-)-N4N for use in generating antibodies in a patient specific for (-)-nicotine. The haptens can be conjugated to suitable carrier proteins and administered as an antigenic mixture, optionally comprising adjuvant(s), to a patient suffering from nicotine or tobacco addiction or habituation.

  该发明提供了手性半抗原(-)-3'-AmNic和(-)-N4N，用于在患有尼古丁或烟草成瘾或习惯的患者中产生特异性于(-)-尼古丁的抗体。这些半抗原可以与适当的载体蛋白结合，并作为抗原混合物施用给患者，可选地包括佐剂。
• METHOD FOR MAKING NICOTINE HAPTEN
  申请人：Nabi Biopharmaceuticals

  公开号：EP1963308A2

  公开（公告）日：2008-09-03
• Method for making nicotine hapten
  申请人：Ennifar Sofiane

  公开号：US20070129551A1

  公开（公告）日：2007-06-07

  A high yielding and short process for preparing the 3′-aminomethylnicotine hapten of general formula I permits the isolation of the hapten in very pure quantities. The process can be adapted for the synthesis of a single stereoisomer or mixtures of stereoisomers, such as the stereoisomers trans-Ia and trans-Ib: Compounds of general formula I are useful for the preparation of hapten-carrier conjugates in the treatment of nicotine addiction.
• ENANTIOPURE HAPTENS FOR NICOTINE VACCINE DEVELOPMENT
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US20170107275A1

  公开（公告）日：2017-04-20

  The invention provides chiral haptens (−)-3′-AmNic and (−)-N4N for use in generating antibodies in a patient specific for (−)-nicotine. The haptens can be conjugated to suitable carrier proteins and administered as an antigenic mixture, optionally comprising adjuvant(s), to a patient suffering from nicotine or tobacco addiction or habituation.
• US7446205B2
  申请人：——

  公开号：US7446205B2

  公开（公告）日：2008-11-04