(+/-)-endo azabicyclo<2.2.1>heptan-3-ol | 21473-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (+/-)-endo azabicyclo<2.2.1>heptan-3-ol
• 英文别名: (±)-(3S,4S)-1-azabicyclo[2.2.1]heptan-3-ol；(3R,4R)-1-azabicyclo[2.2.1]heptan-3-ol
• CAS: 21473-16-5；21473-18-7；138741-10-3；141952-14-9；142034-92-2；142034-93-3
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: RYUPTWCEWSUXQZ-RITPCOANSA-N

物化性质

• 沸点：
  185.4±23.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-endo azabicyclo<2.2.1>heptan-3-ol 在 偶氮二甲酸二异丙酯 、 sodium methylate 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,3R,4S)-3-(3-Hexylsulfanyl-pyrazin-2-yloxy)-1-aza-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Discovery of a highly potent, functionally-selective muscarinic M1 agonist,WAY-132983 using rational drug design and receptor modelling

  摘要：

  Rational drug design utilizing a receptor homology model of the human muscarinic M-1 receptor led to the discovery of the highly potent (K-i = 2 nM), efficacious, and in vivo functionally-selective M-1 agonist, WAY-132983. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00313-3
• 作为产物：
  描述：

  1-氮杂双环[2.2.1]庚烷-3-酮 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以85%的产率得到(+/-)-endo azabicyclo<2.2.1>heptan-3-ol
  参考文献：
  名称：

  Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands

  摘要：

  The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl-based muscarinic receptor ligands ha, been studied, and the exo-azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm00091a007

文献信息

• Substituted-aryl compounds for treatment of disease
  申请人：——

  公开号：US20030236279A1

  公开（公告）日：2003-12-25

  The invention provides compounds of Formula I: 1 These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula I are useful in pharmaceuticals to treat diseases or conditions in which &agr;7 is known to be involved.

  该发明提供了I式化合物：1这些化合物可以是药用盐或组合物的形式，可以是消旋混合物，也可以是其纯对映体。I式化合物在药物中用于治疗已知与α7有关的疾病或症状。
• 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。
• Facile synthesis of the 4-azatricyclo[2.2.1.02,6]heptane system
  作者：Angus M. MacLeod、Richard Herbert、Karst Hoogsteen

  DOI：10.1039/c39900000100

  日期：——

  1-Methoxycarbonyl-4-azatricyclo[2.2.1.02.6]heptane has been prepared by an efficient carbonium ion mediated rearrangement and shown to have a relatively low pKa; the crystal structure of the hydrochloride salt has been determined.

  1-甲氧羰基-4-氮杂三环[2.2.1.0 2.6 ]庚烷是通过有效的碳离子介导的重排制备的，并显示出相对较低的p K a。已经确定了盐酸盐的晶体结构。
• 1,2,5-Thiadiazole Analogues of Aceclidine as Potent m₁ Muscarinic Agonists
  作者：John S. Ward、Leander Merritt、David O. Calligaro、Franklin P. Bymaster、Harlan E. Shannon、Charles H. Mitch、Celia Whitesitt、David Brunsting、Malcolm J. Sheardown、Preben H. Olesen、Michael D. B. Swedberg、Lone Jeppesen、Per Sauerberg

  DOI：10.1021/jm970125n

  日期：1998.1.1

  The acetyl group of the muscarinic agonist aceclidine 4 was replaced by various 1,2,5-thiadiazoles to provide a new series of potent m(1) muscarinic agonists 17 and 18. Optimal mi muscarinic agonist potency was achieved when the 1,2,g-thiadiazole substituent was either a butyloxy, 17d, or butylthio, 18d, group. Although 1,2,5-oxadiazole 37 and pyrazine 39 are iso-pi-electronic with 1,2,5-thiadiazole 17d, both analogues were substantially less active than 17d. Compounds with high muscarinic affinity and/or m(1) muscarinic agonist efficacy were also obtained when the 3-oxyquinuclidine moiety of 17d or 18c was replaced by ethanolamines, hydroxypyrrolidines, hydroxyazetidine, hydroxyisotropanes, or hydroxyazanorbornanes. The structure-activity data support the participation of the oxygen or sulfur atom in the substituent on the 1,2,5-thiadiazole in the activation of the m(1) receptor. Several of these new 1,2,5-thiadiazoles have m(1) agonist efficacy, potency, and selectivity comparable to those of xanomeline 2 in the muscarinic tests investigated.
• MACLEOD, ANGUS M.;HERBERT, RICHARD;HOOGSTEEN, KARST, J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 100-102
  作者：MACLEOD, ANGUS M.、HERBERT, RICHARD、HOOGSTEEN, KARST

  DOI：——

  日期：——