(1S,2S)-N-benzyl-N-methylcyclopentane-1,2-diamine | 928776-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S)-N-benzyl-N-methylcyclopentane-1,2-diamine
• 英文别名: (1S,2S)-1-N-benzyl-1-N-methylcyclopentane-1,2-diamine
• CAS: 928776-91-4
• 化学式: C₁₃H₂₀N₂
• 分子量: 204.315
• InChiKey: RZVSOYGQEATDPB-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (1S,2S)-N-benzyl-N-methylcyclopentane-1,2-diamine 、 吡啶-2,6-二甲醛 、 二碳酸二叔丁酯 在 magnesium sulfate 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 以60%的产率得到di-tert-butyl (pyridine-2,6-diylbis(methylene))bis(((1S,2S)-2-(benzyl(methyl)amino)cyclopentyl)carbamate)
  参考文献：
  名称：

  Cycloalkane-1,2-diamine derivatives as chiral solvating agents. Study of the structural variables controlling the NMR enantiodiscrimination of chiral carboxylic acids

  摘要：

  A family of pincer-like receptors (2-5) has been synthesized and tested for the NMR enantiodiscrimination (CSA) of chiral carboxylic acids. Starting from a previous design (1), different structural variables have been mapped on the receptor frame. The splitting of the signals of the acids upon the addition of the CSAs largely depends on these structural variables. Thus, we concluded that the C-2 symmetrical pyridine-2,6-biscarboxamide moiety is a key structural feature for the efficiency of the CSA. Structural studies by NMR and molecular modeling showed that this moiety promotes the U-shape-folded pincer-like conformation by intramolecular H-bonds. On the other hand, we also observed that the cyclohexane-1,2-diamine derivative 5 is a more versatile CSA than its cyclopentane analogue 1, as 5 shows a better performance for more structurally different acids. However, the original cyclopentane derivative (1) remained the best for the arylpropionic acids. Finally, combination of NMR and modeling studies allowed us to propose a reasonable model for the interaction and, accordingly, for the observed NMR enantiodiscrimination. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.031
• 作为产物：
  描述：

  tert-butyl (1S,2S)-N-[2-(N'-benzyl-N'-methylamino)cyclopentyl]carbamate 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以95%的产率得到(1S,2S)-N-benzyl-N-methylcyclopentane-1,2-diamine
  参考文献：
  名称：

  合成光学活性正交保护的反式-环戊烷-1,2-二胺衍生物的生物催化方法

  摘要：

  光学活性的一种直接的酶化学合成反式- Ñ，Ñ -dialkylcyclopentane -1,2-二胺已经有效地开发从它们的类似（±）起步-反式-2-（Ñ，ñ -二烷基氨基）cyclopentanols。该途径涉及外消旋氨基醇向外消旋二胺的一锅立体定向转化，以及随后借助于来自南极假丝酵母的脂肪酶-B催化的酰化反应的动力学拆分。仔细选择存在于二胺中的烷基取代基和应用于酶促反应的衍生化策略，可以轻松制备其他具有合成价值的光学活性物质反式-环戊烷-1,2-二胺衍生物。

  DOI：

  10.1021/jo062205h

文献信息

• [EN] HETEROARYL COMPOUNDS AND THEIR USE AS THERAPEUTIC DRUGS<br/>[FR] COMPOSÉS HÉTÉROARYLE ET LEUR UTILISATION COMME MÉDICAMENTS THÉRAPEUTIQUES
  申请人：DONG-A SOCIO HOLDINGS CO LTD

  公开号：WO2017039331A1

  公开（公告）日：2017-03-09

  The present invention provides heterocyclic compounds, the stereoisomer thereof, the enantiomer thereof, or the pharmaceutically acceptable salt, which are capable of modulating the activity of Mer receptor tyrosine kinase (MERTK). This invention also provides pharmaceutical compositions thereof, methods to prepare the said compounds, and the use of such compounds as a medicament. The present invention is directed to MERTK inhibitory compounds with marked potency, thereby having an outstanding potential for a pharmaceutical intervention of cancer and any other diseases related to MERTK dysregulation.

  本发明提供了一种杂环化合物、其立体异构体、对映异构体或药用可接受的盐，这些化合物能够调节Mer受体酪氨酸激酶（MERTK）的活性。本发明还提供了这些化合物的药物组合物、制备所述化合物的方法以及将这些化合物用作药物的应用。本发明针对的是具有显著活性的MERTK抑制性化合物，因此具有在癌症和任何与MERTK调控失调相关的疾病中进行药物干预的卓越潜力。
• Heteroaryl compounds and their use as therapeutic drugs
  申请人：Dong-A Socio Holdings Co., Ltd.

  公开号：US10125118B2

  公开（公告）日：2018-11-13

  The present invention provides heterocyclic compounds, the stereoisomer thereof, the enantiomer thereof, or the pharmaceutically acceptable salt, which are capable of modulating the activity of Mer receptor tyrosine kinase (MERTK). This invention also provides pharmaceutical compositions thereof, methods to prepare the said compounds, and the use of such compounds as a medicament. The present invention is directed to MERTK inhibitory compounds with marked potency, thereby having an outstanding potential for a pharmaceutical intervention of cancer and any other diseases related to MERTK dysregulation.

  本发明提供了能够调节Mer受体酪氨酸激酶（MERTK）活性的杂环化合物、其立体异构体、对映体或药学上可接受的盐。本发明还提供了其药物组合物、制备上述化合物的方法以及此类化合物作为药物的用途。 本发明涉及具有显著效力的 MERTK 抑制性化合物，因此在对癌症和任何其他与 MERTK 失调有关的疾病进行药物干预方面具有突出的潜力。
• HETEROARYL COMPOUNDS AND THEIR USE AS THERAPEUTIC DRUGS
  申请人：Dong-A Socio Holdings Co., Ltd.

  公开号：EP3344613A1

  公开（公告）日：2018-07-11
• Cycloalkane-1,2-diamine derivatives as chiral solvating agents. Study of the structural variables controlling the NMR enantiodiscrimination of chiral carboxylic acids
  作者：Carmen Peña、Javier González-Sabín、Ignacio Alfonso、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/j.tet.2008.06.031

  日期：2008.8

  A family of pincer-like receptors (2-5) has been synthesized and tested for the NMR enantiodiscrimination (CSA) of chiral carboxylic acids. Starting from a previous design (1), different structural variables have been mapped on the receptor frame. The splitting of the signals of the acids upon the addition of the CSAs largely depends on these structural variables. Thus, we concluded that the C-2 symmetrical pyridine-2,6-biscarboxamide moiety is a key structural feature for the efficiency of the CSA. Structural studies by NMR and molecular modeling showed that this moiety promotes the U-shape-folded pincer-like conformation by intramolecular H-bonds. On the other hand, we also observed that the cyclohexane-1,2-diamine derivative 5 is a more versatile CSA than its cyclopentane analogue 1, as 5 shows a better performance for more structurally different acids. However, the original cyclopentane derivative (1) remained the best for the arylpropionic acids. Finally, combination of NMR and modeling studies allowed us to propose a reasonable model for the interaction and, accordingly, for the observed NMR enantiodiscrimination. (C) 2008 Elsevier Ltd. All rights reserved.
• A Biocatalytic Approach to Synthesizing Optically Active Orthogonally Protected <i>trans</i>-Cyclopentane-1,2-Diamine Derivatives
  作者：Javier González-Sabín、Vicente Gotor、Francisca Rebolledo

  DOI：10.1021/jo062205h

  日期：2007.2.1

  A straightforward chemoenzymatic synthesis of optically active trans-N,N-dialkylcyclopentane-1,2-diamines has been efficiently developed starting out from their analogous (±)-trans-2-(N,N-dialkylamino)cyclopentanols. The route involves the one-pot stereospecific transformation of the racemic amino alcohols into racemic diamines and a subsequent kinetic resolution by means of lipase-B from Candida

  光学活性的一种直接的酶化学合成反式- Ñ，Ñ -dialkylcyclopentane -1,2-二胺已经有效地开发从它们的类似（±）起步-反式-2-（Ñ，ñ -二烷基氨基）cyclopentanols。该途径涉及外消旋氨基醇向外消旋二胺的一锅立体定向转化，以及随后借助于来自南极假丝酵母的脂肪酶-B催化的酰化反应的动力学拆分。仔细选择存在于二胺中的烷基取代基和应用于酶促反应的衍生化策略，可以轻松制备其他具有合成价值的光学活性物质反式-环戊烷-1,2-二胺衍生物。