2-Cyan-2-adamantanecarbonsaeure-methylester | 128445-55-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Cyan-2-adamantanecarbonsaeure-methylester
• 英文别名: 2-cyano-tricyclo[3.3.1.1(3,7)]decane-2-carboxylic acid methyl ester；Methyl 2-cyanoadamantane-2-carboxylate
• CAS: 128445-55-6
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: OJOCWSRAUYQQRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Cyan-2-adamantanecarbonsaeure-methylester 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 以93%的产率得到2-(2-aminoethyl)tricyclo[3.3.1.1(3,7)]decan-2-ol
  参考文献：
  名称：

  Design and synthesis of bioactive adamantanaminoalcohols and adamantanamines

  摘要：

  Adamantanamines 16, 18, 21, 24, 27, 28, 30, 32, 35, 36, 37, 40, 46 and 48 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. The effect of introducing a hydroxyl group close to the amino group on this class of compounds was examined for the first time. Aminoalcohol 24 proved to be the most active of the compounds tested against influenza A virus, being 6-fold more active than amantadine, equipotent to rimantadine and 26-fold more potent than ribavirin. Aminoalcohols 36 and 37 were found to have considerable activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being almost 10 times more potent than rimantadine. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.009
• 作为产物：
  描述：

  金刚烷-2-腈 、 氯甲酸甲酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以88%的产率得到2-Cyan-2-adamantanecarbonsaeure-methylester
  参考文献：
  名称：

  Design and synthesis of bioactive adamantanaminoalcohols and adamantanamines

  摘要：

  Adamantanamines 16, 18, 21, 24, 27, 28, 30, 32, 35, 36, 37, 40, 46 and 48 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. The effect of introducing a hydroxyl group close to the amino group on this class of compounds was examined for the first time. Aminoalcohol 24 proved to be the most active of the compounds tested against influenza A virus, being 6-fold more active than amantadine, equipotent to rimantadine and 26-fold more potent than ribavirin. Aminoalcohols 36 and 37 were found to have considerable activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being almost 10 times more potent than rimantadine. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.009

文献信息

• N-substituted benzamides and methods of use thereof
  申请人：Genentech, Inc.

  公开号：US08952169B2

  公开（公告）日：2015-02-10

  The invention provides novel compounds having the general formula: and pharmaceutically acceptable salts thereof, wherein the variables RA, subscript n, ring A, X2, L, subscript m, X1, B, R1, R2, R3, R4, R5 and RN have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

  该发明提供了具有以下一般式的新化合物及其药学上可接受的盐： 其中变量RA，下标n，环A，X2，L，下标m，X1，B，R1，R2，R3，R4，R5和RN具有如下所述的含义，以及含有此类化合物的组合物和使用此类化合物和组合物的方法。
• N-SUBSTITUTED BENZAMIDES AND METHODS OF USE THEREOF
  申请人：XENON PHARMACEUTICALS INC.

  公开号：US20130317001A1

  公开（公告）日：2013-11-28

  The invention provides novel compounds having the general formula: and pharmaceutically acceptable salts thereof, wherein the variables R A , subscript n, ring A, X 2 , L, subscript m, X 1 , B, R 1 , R 2 , R 3 , R 4 , R 5 and R N have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

  本发明提供了具有下列一般式的新化合物及其药学上可接受的盐：其中变量RA、下标n、环A、X2、L、下标m、X1、B、R1、R2、R3、R4、R5和RN的含义如本文所述，并且包含这种化合物的组合物和使用这种化合物和组合物的方法。
• Meier, Stefan; Wuerthwein, Ernst-Ulrich, Chemische Berichte, 1990, vol. 123, # 12, p. 2339 - 2347
  作者：Meier, Stefan、Wuerthwein, Ernst-Ulrich

  DOI：——

  日期：——
• Design and synthesis of bioactive adamantane spiro heterocycles
  作者：Nicolas Kolocouris、Grigoris Zoidis、George B. Foscolos、George Fytas、S. Radhika Prathalingham、John M. Kelly、Lieve Naesens、Erik De Clercq

  DOI：10.1016/j.bmcl.2007.04.108

  日期：2007.8

  Spiro[aziridine-2,2'-adamantanes] I and 2, spiro[azetidine-2,2'-adamantanes] 3 and 5, spiro[azetidine-3,2'-adamantane] 13, spiro[piperidine-4,2'-adamantanes] 25 and 27, and spiro barbituric analog 18 were synthesized and tested for their anti-influenza A virus properties and for trypanocidal activity. The effect of ring size on potency was investigated. Piperidine 25 showed significant anti-influenza A virus activity, being 12-fold more active than amantadine, about 2-fold more active than rimantadine, and 54-fold more potent than ribavirin. It also proved to be the most active of the compounds tested against bloodstream forms of the African trypanosome, Trypanosoma brucei, being 1.5 times more potent than rimantadine and at least 25 times more active than amantadine. (c) 2007 Elsevier Ltd. All rights reserved.
• N-SUBSTITUTED BENZAMIDES AND THEIR USE IN THE TREATMENT OF PAIN
  申请人：Genentech, Inc.

  公开号：EP2855428A1

  公开（公告）日：2015-04-08