3-amino-1-azabicyclo<2.2.2>octane-3-carbonitrile | 123194-01-4

• 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: 3-amino-1-azabicyclo<2.2.2>octane-3-carbonitrile
• 英文别名: 3-amino-3-cyanoquinuclidine；3-aminoquinuclidine-3-carbonitrile；3-amino-1-azabicyclo[2.2.2]octane-3-carbonitrile
• CAS: 123194-01-4
• 化学式: C₈H₁₃N₃
• 分子量: 151.211
• InChiKey: WVFQAXXFCPVSED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-1-azabicyclo<2.2.2>octane-3-carbonitrile 在 镍 氨 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以80%的产率得到3-aminomethyl-1-azabicyclo<2.2.2>octyl-3-amine
  参考文献：
  名称：

  (−)-Spiro[1-azabicyclo[2.2.2]octane-3,5‘-oxazolidin-2‘-one], a Conformationally Restricted Analogue of Acetylcholine, Is a Highly Selective Full Agonist at the α7 Nicotinic Acetylcholine Receptor

  摘要：

  Neuronal nicotinic acetylcholine receptors are members of the ligand-gated ion channel receptor superfamily and may play important roles in modulating neurotransmission, cognition, sensory gating, and anxiety. Because of its distribution and abundance in the CNS, the alpha7 nicotinic receptor is a strong candidate to be involved in some of these functions. In this paper we describe the synthesis and in vitro profile of AR-R17779, (-)-spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (4a), a potent full agonist at the rat alpha7 nicotinic receptor, which is highly selective for the rat alpha7 nicotinic receptor over the alpha4 beta2 subtype. Preliminary SAR of AR-R17779 presented here indicate that there is little scope for modification of this rigid molecule as even minor changes result in significant loss of the alpha7 nicotinic receptor affinity.

  DOI：

  10.1021/jm000249r
• 作为产物：
  描述：

  3-羟基喹洛啉-3-甲腈 在 ammonium hydroxide 作用下， 反应 10.0h， 生成 3-amino-1-azabicyclo<2.2.2>octane-3-carbonitrile
  参考文献：
  名称：

  衍生自3-酰氧基-和3-乙酰氨基喹啉环的新型杂环

  摘要：

  通过用碱处理，分别由3-甲酰氧基-，3-乙酰氧基-和3-乙酰酰胺基喹核苷-3-甲腈合成了具有3-螺氧基化的氧杂噻吩啉，呋喃酮和吡咯烷酮杂环的新的奎尼丁衍生物。用氢化钾处理3-乙酰氨基喹啉环-3-甲腈（3）导致脱氰，而烷基锂试剂攻击3中的氰基以产生相应的亚胺。用乙酸钯将3的N-苄基化衍生物氧化环化，得到四环化合物5-乙酰基-1,4-乙醇-1,2,3,4,5,6-六氢苯并[ c ] -1,5-萘啶。

  DOI：

  10.1002/jhet.5570310636

文献信息

• Synthesis of 2′-Arylazabicyclo-3-spiro-4′(5′)-imidazolines
  作者：Brendan Whelan、Isabel Iriepa、Enrique Galvez

  DOI：10.1055/s-1994-25584

  日期：——

  A method is described for the synthesis of a series of 2′-aryl-3-azabicyclospiro-4′ (5′)-imidazolines via the reaction of azabicyclic 1,2-diamines with aryl imidate salts. Competing reactions in the synthesis of the diamines such as the reduction of amino nitriles with LiAlH4 lead to some anomalous products. In the Pinner synthesis, unstable pyridine-type imidates were stabilized as their N-oxide derivatives.

  本文描述了一种通过氮杂双环1,2-二胺与芳基亚氨盐反应合成一系列2′-芳基-3-氮杂双环螺-4′(5′)-咪唑啉的方法。在二胺的合成过程中，如氨基腈与LiAlH4的还原反应等竞争性反应导致一些异常产物的生成。在Pinner合成法中，不稳定的吡啶型亚氨盐被其N-氧化衍生物所稳定化。
• Novel spiro-quinuclidinyl derivatives for the treatment of central nervous system disorders
  申请人：Huang Yifang

  公开号：US20070014751A1

  公开（公告）日：2007-01-18

  The present invention is directed to novel spiro-quinuclidinyl derivatives, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

  本发明涉及新型螺环喹啉基衍生物，包含它们的药物组合物以及它们在治疗中枢神经系统疾病中的用途。
• Novel heterocycles derived from 3-acyloxy- and 3-acetamidoquinuclidines
  作者：Yevgeny Besidsky、Kristina Luthman、Uli Hacksell

  DOI：10.1002/jhet.5570310636

  日期：1994.11

  3-mesyloxy-, 3-acetoxy-, and 3-acetamidoquinuclidine-3-carbonitrile, respectively, by treatment with base. Treatment of 3-acetamidoquinuclidine-3-carbonitrile (3) with potassium hydride resulted in decyanation whereas alkyllithium reagents attacked the cyano group in 3 to produce the corresponding imines. Oxidative cyclization of the N-benzylated derivative of 3 with palladium acetate gave the tetracyclic

  通过用碱处理，分别由3-甲酰氧基-，3-乙酰氧基-和3-乙酰酰胺基喹核苷-3-甲腈合成了具有3-螺氧基化的氧杂噻吩啉，呋喃酮和吡咯烷酮杂环的新的奎尼丁衍生物。用氢化钾处理3-乙酰氨基喹啉环-3-甲腈（3）导致脱氰，而烷基锂试剂攻击3中的氰基以产生相应的亚胺。用乙酸钯将3的N-苄基化衍生物氧化环化，得到四环化合物5-乙酰基-1,4-乙醇-1,2,3,4,5,6-六氢苯并[ c ] -1,5-萘啶。
• Glucosylceramide synthase inhibitors
  申请人：GENZYME CORPORATION

  公开号：US09126993B2

  公开（公告）日：2015-09-08

  The invention relates to inhibitors of glucosylceramide synthase (GCS) useful for the treatment metabolic diseases, such as lysosomal storage diseases, either alone or in combination with enzyme replacement therapy, and for the treatment of cancer.

  该发明涉及对葡萄糖鞘氨醇合成酶（GCS）的抑制剂，用于治疗代谢性疾病，如溶酶体贮积病，可以单独使用或与酶替代疗法结合使用，并用于癌症的治疗。
• GLUCOSYLCERAMIDE SYNTHASE INHIBITORS
  申请人：Genzyme Corporation

  公开号：US20140371460A1

  公开（公告）日：2014-12-18

  The invention relates to inhibitors of glucosylceramide synthase (GCS) useful for the treatment metabolic diseases, such as lysosomal storage diseases, either alone or in combination with enzyme replacement therapy, and for the treatment of cancer.

  本发明涉及一种对糖脂合成酶（GCS）的抑制剂，用于治疗代谢性疾病，例如溶酶体贮存病，可单独使用或与酶替代治疗相结合，并用于治疗癌症。