(1S)-exo-fenchylamine | 131348-10-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S)-exo-fenchylamine
• 英文别名: 1R,2S,4R-fenchylamine；(1S)-2exo-amino-1.3.3-trimethyl-norbornane；(1S)-2exo-Amino-1.3.3-trimethyl-norbornan；(-)-β-Fenchylamin；exo-Fenchylamin；(1S,2R,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-amine
• CAS: 131348-10-2
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: CBYXIIFIKSBHEY-WEDXCCLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 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：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲酸 、 (1S)-exo-fenchylamine 生成 (1S)-2exo-formylamino-1.3.3-trimethyl-norbornane
  参考文献：
  名称：

  Hueckel; Kindler; Wolowski, Chemische Berichte, 1944, vol. 77/79, p. 220,224

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-葑酮 在 吡啶 、 盐酸羟胺 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 (1S)-exo-fenchylamine
  参考文献：
  名称：

  Fenchylamine Sulfonamide Inhibitors of Amyloid β Peptide Production by the γ-Secretase Proteolytic Pathway:  Potential Small-Molecule Therapeutic Agents for the Treatment of Alzheimer's Disease

  摘要：

  DOI：

  10.1021/jm990622z

文献信息

• Sulfamoyl benzamides as novel CB2 cannabinoid receptor ligands
  作者：Karin Worm、Q. Jean Zhou、Christopher T. Saeui、Rosalyn C. Green、Joel A. Cassel、Gabriel J. Stabley、Robert N. DeHaven、Nathalie Conway-James、Christopher J. LaBuda、Michael Koblish、Patrick J. Little、Roland E. Dolle

  DOI：10.1016/j.bmcl.2008.04.006

  日期：2008.5

  Sulfamoyl benzamides were identified as a novel series of cannabinoid receptor ligands. Starting from a screening hit 8 that had modest affinity for the cannabinoid CB(2) receptor, a parallel synthesis approach and initial SAR are described, leading to compound 27 with 120-fold functional selectivity for the CB(2) receptor. This compound produced robust antiallodynic activity in rodent models of postoperative

  氨磺酰基苯甲酰胺被确定为一系列新的大麻素受体配体。从对大麻素CB（2）受体具有适度亲和力的筛选命中8开始，描述了一种平行合成方法和初始SAR，从而导致化合物27对CB（2）受体的功能选择性为120倍。该化合物在术后疼痛和神经性疼痛的啮齿动物模型中产生了强大的抗痛觉过敏活性，而没有传统的大麻素副作用。
• Alder; Stein, Justus Liebigs Annalen der Chemie, 1936, vol. 525, p. 247,252, 258
  作者：Alder、Stein

  DOI：——

  日期：——
• Hueckel; Scheel, Justus Liebigs Annalen der Chemie, 1963, vol. 664, p. 19,27
  作者：Hueckel、Scheel

  DOI：——

  日期：——
• Tricyclic pyrazoles part 7. Discovery of potent and selective dihydrothienocyclopentapyrazole derived CB2 ligands
  作者：Giansalvo Pinna、Maria Michela Curzu、Antonio Dore、Paolo Lazzari、Stefania Ruiu、Amedeo Pau、Gabriele Murineddu、Gérard A. Pinna

  DOI：10.1016/j.ejmech.2014.08.042

  日期：2014.10

  A series of dihydrothienocyclopentapyrazole-based derivatives was synthesized and evaluated for the affinity at CBI and CB2 receptors. The major term, the 6-methyl-1-(1,4-dichloropheny1)-N-piperidiny1)-1,4-dihydrothieno[2',3'-4,5]cyclopenta[1,2-c]pyrazole-3-carboxamide (6a), displayed a high affinity and good selectivity for CB2 receptors (Ki values of 2.30 nM for CB2 receptor and 440 nM for CB1 receptors respectively). Subsequent analogue preparation resulted in the identification of compounds such as 6b, 6d, 6e, 6k, 6l, 6m, 6s and 6t that showed 1.3-485 fold selectivity for CB2 receptors with potencies in the 1.1-7.2 nM range. These compounds profiled as full agonists at CB2 receptor in an inhibition assay of P-ERK 1/2 up regulation in HL-60 cells. (C) 2014 Elsevier Masson SAS. All rights reserved.