3-[(1R,9aR)-octahydro-1H-quinolizin-1-yl]propan-1-amine | 127709-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: 3-[(1R,9aR)-octahydro-1H-quinolizin-1-yl]propan-1-amine
• 英文别名: 3-Chinolizidin-1-α'-yl-propylamin；3-[(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]propan-1-amine
• CAS: 127709-15-3
• 化学式: C₁₂H₂₄N₂
• 分子量: 196.336
• InChiKey: HWLHIWRFGSEZDR-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(1R,9aR)-octahydro-1H-quinolizin-1-yl]propan-1-amine 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 5.0h， 生成 2-(4-chloroanilino)-5-(4-chlorophenyl)-3-{[(1S,9aR)-(octahydro-2H-quinolizin-1-yl)propyl]imino}-3,5-dihydrophenazine monohydrochloride
  参考文献：
  名称：

  Antitubercular activity of quinolizidinyl/pyrrolizidinylalkyliminophenazines

  摘要：

  Novel riminophenazine derivatives, characterized by the presence of the basic and cumbersome quinolizidinylalkyl and pyrrolizidinylethyl moieties, have been synthesized and tested (Rema test) against Mycobacterium tuberculosis H37Rv and H37Ra, and six clinical isolates of Mycobacterium avium and Mycobacterium tuberculosis. Most compounds exhibited potent activity against the tested strains, resulting more active than clofazimine, isoniazid and ethambutol.The best compounds (4, 5, 12 and 13) exhibited a MIC in the range 0.82-0.86 mu M against all strains of Mycobacterium tuberculosis and, with the exception of 4 a MIC around 3.3 mu M versus M. avium. The corresponding values for clofazimine (CFM) were 1.06 and 4.23 mu M, respectively. Cytotoxicity was evaluated against three cell lines and compound 4 displayed a selectivity index (SI) versus the human cell line MT-4 comparable with that of CFM (SI = 5.23 vs 6.4). Toxicity against mammalian Vero 76 cell line was quite lower with SI = 79. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.10.035

文献信息

• Multitarget Therapeutic Leads for Alzheimer’s Disease: Quinolizidinyl Derivatives of Bi- and Tricyclic Systems as Dual Inhibitors of Cholinesterases and β-Amyloid (Aβ) Aggregation
  作者：Michele Tonelli、Marco Catto、Bruno Tasso、Federica Novelli、Caterina Canu、Giovanna Iusco、Leonardo Pisani、Angelo De Stradis、Nunzio Denora、Anna Sparatore、Vito Boido、Angelo Carotti、Fabio Sparatore

  DOI：10.1002/cmdc.201500104

  日期：2015.6

  displayed inhibitory activity on both AChE and BChE and on the spontaneous aggregation of β‐amyloid. In most cases, IC50 values were in the low micromolar and sub‐micromolar range, but some compounds even reached nanomolar potency. The time course of amyloid aggregation in the presence of the most active derivative (IC50=0.84 μM) revealed that these compounds might act as destabilizers of mature fibrils

  在能够维持或恢复细胞蛋白稳态并抑制β-淀粉样蛋白（Aβ）寡聚化的化合物模型上设计了阿尔茨海默氏病的多靶点治疗药物。测试了37种噻吨酮9‐1，黄嘌呤‐9‐1，萘酚和蒽醌衍生物对Aβ（1-40）聚集的直接抑制作用以及对电鳗乙酰胆碱酯酶（eeAChE）和马血清丁酰胆碱酯酶（ hsBChE）。这些化合物的特征是与各种双环和三环（杂）芳族体系连接的碱性侧链（主要是喹啉亚二烷基烷基）。除极少数例外，这些化合物均对AChE和BChE以及对β-淀粉样蛋白的自发聚集均具有抑制活性。在大多数情况下，IC 50值在低微摩尔和亚微摩尔范围内，但有些化合物甚至达到了纳摩尔效价。在最活跃的衍生物的存在淀粉状蛋白聚集的时间过程（IC 50 = 0.84μ中号）揭示了这些化合物还不如成熟的纤维，而不是原纤维化的单纯的抑制剂的去稳定作用。许多化合物以相似的效力抑制胆碱酯酶和Aβ聚集中的一种或两种，这是可能开发出具有多目标作
• Clofazimine analogs with antileishmanial and antiplasmodial activity
  作者：Anna Barteselli、Manolo Casagrande、Nicoletta Basilico、Silvia Parapini、Chiara M. Rusconi、Michele Tonelli、Vito Boido、Donatella Taramelli、Fabio Sparatore、Anna Sparatore

  DOI：10.1016/j.bmc.2014.11.028

  日期：2015.1

  A set of novel riminophenazine derivatives has been synthesized and evaluated for in vitro activity against chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) strains of Plasmodium falciparum and against different species of Leishmania promastigotes. Most of the new compounds inhibited the growth of Leishmania promastigotes as well as CQ-S and CQ-R strains of P. falciparum with IC50 in submicromolar range, resulting in the best cases 1-2 orders of magnitude more potent than the parent compound clofazimine. (C) 2014 Elsevier Ltd. All rights reserved.
• Canu; Iusco; Boido, Il Farmaco, 1989, vol. 44, # 11, p. 1069 - 1082
  作者：Canu、Iusco、Boido、Sparatore、Sparatore

  DOI：——

  日期：——