2-aminomethyl-1-azabicyclo[2.2.2]octane | 62190-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 2-aminomethyl-1-azabicyclo[2.2.2]octane
• 英文别名: C-quinuclidin-2-yl-methylamine；C-Chinuclidin-2-yl-methylamin；1-azabicyclo[2.2.2]octan-2-methanamine；2-(aminomethyl)-quinuclidine；{1-Azabicyclo[2.2.2]octan-2-yl}methanamine；1-azabicyclo[2.2.2]octan-2-ylmethanamine
• CAS: 62190-20-9
• 化学式: C₈H₁₆N₂
• mdl: MFCD19204906
• 分子量: 140.228
• InChiKey: XVCFWFMLNSQUKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  racemic-1-azabicyclo[2.2.2]octane-2-carbonyl chloride hydrochloride 、 2-aminomethyl-1-azabicyclo[2.2.2]octane 以70%的产率得到
  参考文献：
  名称：

  BULACINSKI, A. B.;GUTKOWSKA, B., ACTA POL. PHARM., 1984, 41, N 4, 441-446

  摘要：

  DOI：
• 作为产物：
  描述：

  2-亚甲基奎宁环-3-酮 在 氯化亚砜 、 palladium on activated charcoal 、 氨 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 94.5h， 生成 2-aminomethyl-1-azabicyclo[2.2.2]octane
  参考文献：
  名称：

  Synthesis and Nicotinic Receptor Activity of Chemical Space Analogues of N-(3R)-1-Azabicyclo[2.2.2]oct-3-yl-4-chlorobenzamide (PNU-282,987) and 1,4-Diazabicyclo[3.2.2]nonane-4-carboxylic Acid 4-Bromophenyl Ester (SSR180711)

  摘要：

  The Chemical Universe Generated Databases up to 11 atoms of CNOF (GDB-11) and up to 13 atoms of CNOClS (GDB-13) were used to enumerate analogues of the diamine part of two known alpha 7 nicotinic receptor agonists and construct libraries of virtual analogues of these drugs. The libraries were scored using structure-based (docking to the nicotine binding site of the acetylcholine binding protein 1uw6.pdb) or ligand-based (similarity to the parent drugs) methods, and the top-scoring virtual ligands were inspected for easily accessible synthetic targets. In total, 21 diamines were prepared and acylated with aromatic carboxylic or oxycarbonic acids to produce 85 analogues of the parent drugs. The compounds were profiled by electrophysiology in Xenopus oocytes expressing human nicotinic acetylcholine receptor (nAChR) subtypes alpha 7, alpha 3 beta 2, alpha 4 beta 2, alpha 3 beta 4, or alpha 4 beta 4. Characterization of selected compounds revealed eight inhibitors of the alpha 7 nicotinic receptor and three positive allosteric modulators of the alpha 3 beta 2 nAChR.

  DOI：

  10.1021/jm300030r

文献信息

• Antiemetic, psychosomatic and antipsychotic heterocyclic pyridine
  申请人：Ciba-Geigy Corporation

  公开号：US04089960A1

  公开（公告）日：1978-05-16

  The present invention provides new basically substituted pyridinecarboxamides having the formula I ##STR1## wherein R.sub.1 represents lower alkyl and --OR.sub.1 is in the adjacent position to the carboxamide group, R.sub.2 represents lower alkyl or an ethylene radical which is attached to one of the trivalent radicals designated as A and the nitrogen atom located between it to form a 6-membered ring, A represents a divalent saturated hydrocarbon radical which encompasses at most a single ring with 5 or 6 ring members and contains not more than 7 carbon atoms and whose two linkage positions are separated by (3-m) to 4 carbon atoms, or, if R.sub.2 is an ethylene radical, represents the 1-propanyl-3-ylidene radical, if m s 1, or the 1,2,4-butane-triyl radical, if m is 0, And one of the factors m and n is 0 and the other is 1, and, if desired, the ring B is further substituted, and the acid addition salts of the compounds of the formula I. These new substances possess useful pharmacological properties, in particular antiemetic, psychosomatic and antipsychotic activity and can be used for the treatment of thought disturbances and of states of psychomotor excitation. Specific embodiments are N-[(1-ethyl-2-pyrrolidinyl)-methyl]-2,6-dimethoxynicotinamide and the pharmaceutically acceptable acid addition salts thereof.

  本发明提供了一种新的基本取代吡啶羧酰胺，其具有以下式I ##STR1## 其中R.sub.1代表较低的烷基，--OR.sub.1位于与羧酰胺基团相邻的位置，R.sub.2代表较低的烷基或与被标记为A的三价基团之一和位于其之间的氮原子形成6元环的乙烯基，A代表二价饱和碳氢基团，最多包含一个由5或6个环成员组成的环，并且含有不超过7个碳原子，其两个连接位置之间相隔(3-m)至4个碳原子，或者如果R.sub.2是一个乙烯基，则代表1-丙基-3-亚基基团，如果m≤1，或者1,2,4-丁烷三基基团，如果m为0，而m和n中的一个因子为0，另一个为1，如果需要，环B进一步取代，并且具有上述式I的化合物的酸盐加合物。这些新物质具有有用的药理特性，特别是抗恶心、精神身体反应和抗精神病活性，并可用于治疗思维障碍和精神运动兴奋状态。具体实施例包括N-[(1-乙基-2-吡咯烷基)-甲基]-2,6-二甲氧基烟酰胺及其药用可接受的酸盐加合物。
• Process for preparing 63-carboxyamides of teicoplanin antibiotics
  申请人：GRUPPO LEPETIT S.p.A.

  公开号：EP0370283A2

  公开（公告）日：1990-05-30

  The present invention is directed to an improved process for preparing 63 carboxyamides of teicoplanin (eventually having ¹⁵-N-alkyl substituents) by reacting a teicoplanin like compound with an activated ester forming reagent to give an ester function which is substituted by an amine, by contacting an excess of said amine in an organic polar solvent at a temperature comprised between 5°C and 60°C.

  本发明涉及一种用于制备 63 种茶碱羧酰胺（最终具有 ¹⁵-N-烷基取代基）的改进工艺，其方法是将茶碱类化合物与活化的酯形成试剂反应，得到被胺取代的酯官能团，将过量的所述胺在有机极性溶剂中接触，温度在 5°C 至 60°C 之间。
• Prelog; Rajner; Stern, Helvetica Chimica Acta, 1943, vol. 26, p. 1176
  作者：Prelog、Rajner、Stern

  DOI：——

  日期：——
• BULACINSKI, ANDRZEJ BENEDYKT;GUTKOWSKA, BOZENA, ACTA POL. PHARM, 44,(1987) N 1, 16-20
  作者：BULACINSKI, ANDRZEJ BENEDYKT、GUTKOWSKA, BOZENA

  DOI：——

  日期：——
• GUTKOWSKA B.; ROGALA-ZAWADZKA G., ACTA POL. PHARM., 43,(1986) N 5, 406-410
  作者：GUTKOWSKA B.、 ROGALA-ZAWADZKA G.

  DOI：——

  日期：——