(R)-N-(α-cyclohexylethyl)-N-methylamine | 163667-49-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-N-(α-cyclohexylethyl)-N-methylamine
• 英文别名: (R)-N-methyl-N-(α-cyclohexylethyl)amine；(-)-N-methyl-1-cyclohexylethylamine；[(1R)-1-cyclohexyl-ethyl]-methylamine；[(1R)-1-cyclohexylethyl](methyl)amine；(1R)-1-cyclohexyl-N-methylethanamine
• CAS: 163667-49-0
• 化学式: C₉H₁₉N
• 分子量: 141.257
• InChiKey: HMJRHWDZXQWZRU-MRVPVSSYSA-N

物化性质

• 沸点：
  175.4±8.0 °C(Predicted)
• 密度：
  0.843±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-N-(α-cyclohexylethyl)-N-methylamine 、 吡咯-2-羧酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到N-[(1R)-1-cyclohexylethyl]-N-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  New Pyrrole Inhibitors of Monoamine Oxidase:  Synthesis, Biological Evaluation, and Structural Determinants of MAO-A and MAO-B Selectivity

  摘要：

  A series of new pyrrole derivatives have been synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. N-Methyl,N-(benzyl),N-(pyrrol-2-ylmethyl)amine (7) and N-(2-benzyl),N-(1-methylpyrrol-2-ylmethyl)amine (18) were the most selective MAO-B (7, SI = 0.0057) and MAO-A (18, SI = 12500) inhibitors, respectively. Docking and molecular dynamics simulations gave structural insights into the MAO-A and MAO-B selectivity. Compound 18 forms an H-bond with Gln215 through its protonated amino group into the MAO-A binding site. This H-bond is absent in the 7/MAO-A complex. In contrast, compound 7 places its phenyl ring into an aromatic cage of the MAO-B binding pocket, where it forms charge-transfer interactions. The slightly different binding pose of 18 into the MAO-B active site seems to be forced by a bulkier Tyr residue, which replaces a smaller Ile residue present in MAO-A.

  DOI：

  10.1021/jm060882y
• 作为产物：
  描述：

  ethyl (R)-(α-cyclohexylethyl)carbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到(R)-N-(α-cyclohexylethyl)-N-methylamine
  参考文献：
  名称：

  新型单胺氧化酶A和B的吲哚抑制剂的合成，构效关系和分子模型研究。

  摘要：

  合成了新的单胺氧化酶抑制剂，作为先前报道的吡咯系列的吲哚类似物。几种化合物是有效的MAO-A（12、17、19-22、31、36和37）或MAO-B（14、20、24、38、44和46）抑制剂，具有K（i）值在纳摩尔浓度范围内。特别地，22（K（i）= 0.00092 microM，SI = 68,478）作为MAO-A抑制剂异常有效且具有选择性。在分子建模研究中，化合物22、24、44和46将吲哚环置于MAO-A的芳香腔中，并与Tyr407，Tyr444和FAD辅因子建立了pi-pi堆积相互作用。但是，只有化合物22能够与FAD形成氢键，这一发现与其有效的抗MAO-A活性相符。相反，在MD模拟过程中22 / MAOB复合物高度不稳定。

  DOI：

  10.1016/j.bmc.2008.09.072

文献信息

• Tetrahydro-indazole cannabinoid modulators
  申请人：Lagu Bharat

  公开号：US20050228034A1

  公开（公告）日：2005-10-13

  This invention is directed to a tetrahydro-indazole cannabinoid modulator compound of formula I: and a method for use in treating, ameliorating or preventing a cannabinoid receptor mediated syndrome, disorder or disease.

  这项发明涉及一种式I的四氢吲哚类大麻素调节剂化合物，以及一种用于治疗、改善或预防大麻素受体介导的综合症、紊乱或疾病的方法。
• PYRIMIDINE COMPOUND
  申请人：Matsushima Yuji

  公开号：US20110053912A1

  公开（公告）日：2011-03-03

  A novel and excellent method for preventing and/or treating diseases related to a cannabinoid type 2 receptor, based on an agonistic action on a cannabinoid type 2 receptor. It was found that a hetero ring derivative mainly having two substituents, for example, a pyrimidine-5-carboxamide derivative having a substituent amino group at the 2-position, exhibits a potent agonistic action on a cannabinoid type 2 receptor, and can be an agent for preventing and/or treating diseases related to a cannabinoid type 2 receptor such as inflammatory diseases, pain, and the like.

  一种预防和/或治疗与大麻素2型受体相关疾病的新颖优秀方法，基于对大麻素2型受体的激动作用。发现一种异核环衍生物主要具有两个取代基，例如，在2-位置具有取代基氨基的嘧啶-5-羧酰胺衍生物，表现出对大麻素2型受体的强效激动作用，可以成为预防和/或治疗与大麻素2型受体相关疾病，如炎症性疾病、疼痛等的药物。
• [EN] NEW COMPOUNDS FOR THE TREATMENT OF DISEASES RELATED TO PROTEIN MISFOLDING<br/>[FR] NOUVEAUX COMPOSÉS POUR LE TRAITEMENT DE MALADIES LIÉES À UN MAUVAIS REPLIEMENT DE PROTÉINES
  申请人：UNIV DUISBURG ESSEN

  公开号：WO2011050864A1

  公开（公告）日：2011-05-05

  The present invention relates to the field of protein misfolding diseases and thus to diseases which are associated with or induced by abnormal or pathogenic three-dimensional folding of proteins and/or peptides or which are linked to pathogenic conformational changes of proteins and/or peptides, such as Alzheimer's disease. Particularly, the present invention provides novel trimeric pyrazole compounds, which exhibit a therapeutic effectiveness in regard to the aforementioned protein misfolding diseases, and refers to their use for the treatment of such protein misfolding diseases, especially neurodegenerative diseases as well as to medicaments or pharmaceutical compositions comprising these compounds.

  本发明涉及蛋白质错折疾病领域，因此涉及与异常或致病性蛋白质和/或肽的三维折叠相关或诱导的疾病，或与致病性蛋白质和/或肽的构象变化相关的疾病，如阿尔茨海默病。具体地，本发明提供了新型三聚吡唑化合物，这些化合物在治疗上述蛋白质错折疾病方面表现出治疗有效性，并涉及其用于治疗此类蛋白质错折疾病，特别是神经退行性疾病，以及包含这些化合物的药物或制剂组合物。
• Enantioselective Protonation of Lithium Enolates with Chiral Imides Possessing a Chiral Amide
  作者：Akira Yanagisawa、Tetsuo Kikuchi、Tsuyoshi Watanabe、Hisashi Yamamoto

  DOI：10.1246/bcsj.72.2337

  日期：1999.10

  New chiral imides possessing a chiral amide can be prepared from 1,3,5-trimethyl-r-1,c-3,c-5-cyclohexanetricarboxylic acid or related triacids and optically active amines. These imides are superior to 1,3,5-trimethyl-c-5-[(4S,5S)-4,5-diphenyl-2-oxazolin-2-yl]-r-1,c-3-cyclohexanedicarboximide reported previously as a chiral proton source for enantioselective protonation of lithium enolates of 2-alkylcycloalkanones

  具有手性酰胺的新型手性酰亚胺可由1,3,5-三甲基-r-1,c-3,c-5-环己烷三羧酸或相关的三酸和旋光胺制备。这些酰亚胺优于先前报道的 1,3,5-三甲基-c-5-[(4S,5S)-4,5-二苯基-2-恶唑啉-2-基]-r-1,c-3-环己烷二甲酰亚胺作为手性质子源，用于 2-烷基环烷酮的锂烯醇化物的对映选择性质子化。
• Chemical Compounds
  申请人：Kerns K. Jeffrey

  公开号：US20070254873A1

  公开（公告）日：2007-11-01

  The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及新型吲哚羧酰胺衍生物。具体而言，本发明涉及公式I所示的化合物：其中R1，R2，R3，U和V如下所定义，及其药学上可接受的盐。本发明的化合物是IKK2的抑制剂，可用于治疗与不适当的IKK2（也称为IKKβ）活性有关的疾病，如类风湿性关节炎、哮喘和COPD（慢性阻塞性肺疾病）。因此，本发明还涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明化合物或包含本发明化合物的药物组合物来抑制IKK2活性和治疗与此相关的疾病的方法。