4-氨基-3-氰基-1,2,5,6-四氢吡啶 | 15827-80-2

• 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
• 中文名称: 4-氨基-3-氰基-1,2,5,6-四氢吡啶
• 英文名称: 4-amino-3-cyano-1,2,5,6-tetrahydropyridine
• 英文别名: 4-Amino-3-cyan-1,2,5,6-tetrahydropyridin；4-Amino-3-cyano-1,2,3,6-tetrahydropyridin；4-Amino-3-cyano-piperidin-3-en；4-amino-1,2,3,6-tetrahydropyridine-5-carbonitrile
• CAS: 15827-80-2
• 化学式: C₆H₉N₃
• mdl: MFCD04038471
• 分子量: 123.158
• InChiKey: SNDHGRMHEXOIHX-UHFFFAOYSA-N

物化性质

• 沸点：
  366.4±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-氨基-3-氰基-1,2,5,6-四氢吡啶 在 盐酸 、 三正丙胺 、 sodium hydroxide 、 sodium ethanolate 、 碳酸氢钠 作用下， 以 乙醇 、 乙二醇甲醚 、 丁酮 为溶剂， 反应 24.0h， 生成 4-(2-fluorophenyl)-7-oxo-N-phenyl-3,5,6,8,12-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4-triene-12-carboxamide
  参考文献：
  名称：

  Anxiolytic properties of certain annelated [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones

  摘要：

  Modification of the benzodiazepine (BZ) receptor binding template 2-aryl[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one by replacement of the annelated benzene ring with various alicyclic and heterocyclic moieties led to novel structures with potent BZ receptor binding affinity. High affinity was found in some cycloalkyl-annelated [1,2,4]triazolo-[1,5-c]pyrimidin-5(6H)-ones and in some 7,8,9,10-tetrahydropyrido[3,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones, in which the degree of activity was strongly dependent on the N-substituent in the 9-position. Nine compounds with BZ receptor IC50 binding affinity values equal or superior to diazepam were evaluated in secondary screening. One of these, 9-benzyl-2-phenyl-7,8,9,10-tetrahydropyrido[3,4-e]?? [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one, showed good activity in rats as a potential anxiolytic agent without sedative liability. However, it increased the rotorod deficit produced by ethanol at anxiolytic doses, an indication of alcohol interaction. Thus, none of the compounds showed an advantage over CGS 9896 (Yokoyama et al. J. Med. Chem. 1982, 25, 337-339), which is free of sedative and alcohol interaction potential as measured by the test procedures described.

  DOI：

  10.1021/jm00113a032
• 作为产物：
  描述：

  双(2-氰基乙基)胺 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 生成 4-氨基-3-氰基-1,2,5,6-四氢吡啶
  参考文献：
  名称：

  Anxiolytic properties of certain annelated [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones

  摘要：

  Modification of the benzodiazepine (BZ) receptor binding template 2-aryl[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one by replacement of the annelated benzene ring with various alicyclic and heterocyclic moieties led to novel structures with potent BZ receptor binding affinity. High affinity was found in some cycloalkyl-annelated [1,2,4]triazolo-[1,5-c]pyrimidin-5(6H)-ones and in some 7,8,9,10-tetrahydropyrido[3,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones, in which the degree of activity was strongly dependent on the N-substituent in the 9-position. Nine compounds with BZ receptor IC50 binding affinity values equal or superior to diazepam were evaluated in secondary screening. One of these, 9-benzyl-2-phenyl-7,8,9,10-tetrahydropyrido[3,4-e]?? [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one, showed good activity in rats as a potential anxiolytic agent without sedative liability. However, it increased the rotorod deficit produced by ethanol at anxiolytic doses, an indication of alcohol interaction. Thus, none of the compounds showed an advantage over CGS 9896 (Yokoyama et al. J. Med. Chem. 1982, 25, 337-339), which is free of sedative and alcohol interaction potential as measured by the test procedures described.

  DOI：

  10.1021/jm00113a032

文献信息

• PYRAZOLOPYRIDINE DERIVATIVE HAVING GLP-1 RECEPTOR AGONIST EFFECT
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20190225604A1

  公开（公告）日：2019-07-25

  The present invention provides a compound having the basic structure shown by Formula (I) in which the indole ring and the pyrazolopyridine structure is bound through a substituent, a salt thereof or a solvate of either the compound or a salt of the compound, as well as a preventative agent or a therapeutic agent for non-insulin-dependent diabetes mellitus (Type 2 diabetes) or obesity containing such compound, salt or solvate as an active ingredient.

  本发明提供一种化合物，其具有通过取代基连接的式（I）所示的基本结构，其中吲哚环和吡唑吡啶结构通过取代基相连，以及包含该化合物、盐或该化合物的盐的溶剂的预防剂或治疗剂，用作非胰岛素依赖型糖尿病（2型糖尿病）或肥胖症的活性成分。
• 2-(aminoaryl) indoles and indolines as topical antiinflammatory agents
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05166170A1

  公开（公告）日：1992-11-24

  There are disclosed various compounds depicted by the general formula, ##STR1## where the parameters X, Y, R.sub.1, R.sub.2, and R.sub.3 are as defined in the specification. These compounds are disclosed as topical antiinflammatory agents useful for the treatment of various skin disorders including exogenous dermatitis, endogenous dermatitis, dermatitis of unknown etiology and other cutaneous disorders with an inflammatory component.

  公开了各种化合物，其通式如下：##STR1## 其中参数X、Y、R.sub.1、R.sub.2和R.sub.3的定义如规范中所述。这些化合物被公开为局部抗炎剂，可用于治疗各种皮肤疾病，包括外源性皮炎、内源性皮炎、原因不明的皮炎和其他具有炎症成分的皮肤疾病。
• Synthesis and Biological Evaluation of 7,8,9,10-Tetrahydroimidazo[1,2-<i>c</i>]pyrido[3,4-<i>e</i>]pyrimdin-5(6H)-ones as Functionally Selective Ligands of the Benzodiazepine Receptor Site on the GABA_A Receptor
  作者：Pamela A. Albaugh、Lu Marshall、James Gregory、Geoff White、Alan Hutchison、Phil C. Ross、Dorothy W. Gallagher、John F. Tallman、Matt Crago、James V. Cassella

  DOI：10.1021/jm0202019

  日期：2002.11.1

  benzodiazepines are nonselective and suffer from numerous side effects. Upon the identification of receptor subtypes, we set out to discover selective agents with the anticipation that these agents would have superior therapeutic potential. Herein, we describe the synthesis and biological evaluation of substituted 7,8,9,10-tetrahydroimidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-ones and disclose that these compounds

  苯二氮卓类是GABA（A）受体的变构调节剂。传统上规定的苯二氮杂类是非选择性的，并且具有许多副作用。在鉴定受体亚型后，我们着手发现选择性药物，并期望这些药物具有更高的治疗潜力。在这里，我们描述了取代的7,8,9,10-四氢咪唑并[1,2-c]吡啶并[3,4-e]嘧啶-5（6H）-的合成及生物学评价，并揭示了这些化合物具有一定的功能。对GABA（A）受体亚型的苯二氮卓受体的选择性。alpha（2）/ alpha（3）-选择性部分激动剂42表现出强大的体内活性。
• Certain azacycloalkyl imidazopyrimidines; a new class of GABA brain
  申请人：Neurogen Corporation

  公开号：US05095015A1

  公开（公告）日：1992-03-10

  The invention encompasses compounds of the formula: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof where n is 0, 1, or 2 and x is ##STR2## and R.sub.1, R.sub.2, R.sub.3, Y, Z, W, T are defined variables. These compounds are highly selective agonists or inverse agonists for the GABAa brain receptors and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine type drugs, and enhancement of alertness.

  该发明涵盖了公式为：##STR1##和其药学上可接受的非毒性盐，其中n为0、1或2，x为##STR2##，而R.sub.1、R.sub.2、R.sub.3、Y、Z、W、T是定义变量。这些化合物是高度选择性的GABAa脑受体激动剂或反向激动剂，并且在焦虑、睡眠和癫痫障碍、苯二氮卓类药物过量和警觉性增强的诊断和治疗中非常有用。
• Certain aryl fused imidazopyrimidines; a new class of GABA brain
  申请人：Neurogen Corporation

  公开号：US06013650A1

  公开（公告）日：2000-01-11

  Disclosed is a method for treating a subject non-human animal or domestic pet exhibiting symptoms of anxiety with a compound of the formula: ##STR1## wherein X is oxygen or sulfur; W is (un)substituted phenyl, thienyl or pyridyl; and ##STR2## represents (un)substituted aryl or heteroaryl as defined in the specification.

  本发明公开了一种用式子所示的化合物治疗表现出焦虑症状的非人类动物或家养宠物的方法：##STR1## 其中X是氧或硫；W是（未）取代的苯基，噻吩基或吡啶基；以及##STR2##代表（未）取代的芳基或杂环芳基，如规范中定义的那样。