2-ethyl-quinoline-3-carboxylic acid | 888069-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-ethyl-quinoline-3-carboxylic acid
• 英文别名: 2-Ethylquinoline-3-carboxylic acid
• CAS: 888069-31-6
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: VTRUZSBNPFFWIO-UHFFFAOYSA-N

物化性质

• 沸点：
  332.3±27.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethyl-quinoline-3-carboxylic acid 、 Fmoc-L-脯氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-L-烯丙基甘氨酸 、 1,3-丙二胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 1.5h， 以0.23 g的产率得到N-[(2S)-1-[(2S)-2-[[(2S)-1-(3-aminopropylamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopent-4-en-2-yl]-2-ethylquinoline-3-carboxamide
  参考文献：
  名称：

  Strategies for Recognition of Stem−Loop RNA Structures by Synthetic Ligands: Application to the HIV-1 Frameshift Stimulatory Sequence

  摘要：

  Production of the Gag-Pol polyprotein in human immunodeficiency virus (HIV) requires a -1 ribosomal frameshift, which is directed by a highly conserved RNA stern-loop. Building on our discovery of a set of disulfide-containing peptides that bind this RNA, we describe medicinal chemistry efforts designed to begin to understand the structure-activity relationships and RNA sequence-selectivity relationships associated with these compounds. Additionally, we have prepared analogues incorporating an olefin or saturated hydrocarbon bioisostere of the disulfide moiety, as a first step toward enhancing biostability. The olefin-containing compounds exhibit affinity comparable to the lead disulfide and, importantly, have no discernible toxicity when incubated with human fibroblasts at concentrations up to 1 mM.

  DOI：

  10.1021/jm100231t
• 作为产物：
  描述：

  3-氧代戊酸甲酯 、 2-氨基苯甲醛 以 甲苯 为溶剂， 反应 24.0h， 以94%的产率得到2-ethyl-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Quinoline- and 1,8-naphthyridine-3-carboxylic acids using a self-catalyzed Friedländer approach

  摘要：

  One-step syntheses of 2-alkyl- and 2,4-dialkyl-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids are reported using a catalyst-free Friedlander reaction. The reaction is carried out in one step by simple heating of 2-aminobenzaldehyde, 2-amino-5-chlorobenzaldehyde, 2-aminonicotinaldehyde, or 2-aminoacetophenone with a beta-ketoester in toluene or xylene for 24 h. Under these conditions, the carboxylic acid product is isolated directly from the reaction mixture without need for further purification. The observation that the reaction starts slowly and accelerates as it proceeds suggests that the transformation is self-catalyzed. This hypothesis is also supported by the finding that attempts to extend the current reaction to diketones, which cannot hydrolyze to an acid, were generally unsuccessful. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.010

文献信息

• Nucleic acid binding compounds and methods of use
  申请人：Miller Benjamin L.

  公开号：US09212205B2

  公开（公告）日：2015-12-15

  The present invention relates to homo- and hetero-dimer compounds formed by a disulfide, sulfinyl thio, or olefin bond between two monomers. A method of making a homo- or hetero-dimer compound is also disclosed. The present invention also relates to monomer compounds capable of forming homo- or hetero-dimer compounds, as well as oligomers formed via linkage of one or more dimers. Also disclosed are methods of inhibiting the activity of target RNA molecules, particularly those having a secondary structure that include a stem or stem-loop formation. Dimer compounds capable of inhibiting the activity of an HIV-I RNA frameshifting stem-loop and a (CUG)n expanded repeat stem-loop are disclosed, as are methods of treating diseases associated with these target RNA molecules. The dimer compounds can also be used for selectively detecting presence of the target RNA molecule in a sample.

  本发明涉及由两个单体之间的二硫键、亚砜硫或烯烃键形成的同源和异源二聚体化合物。还公开了一种制备同源或异源二聚体化合物的方法。本发明还涉及能够形成同源或异源二聚体化合物的单体化合物，以及通过连接一个或多个二聚体形成的寡聚物。还公开了一种抑制目标RNA分子活性的方法，特别是那些具有包括茎或茎环形成的次级结构的RNA分子。公开了能够抑制HIV-I RNA移码茎环和(CUG)n扩展重复茎环活性的二聚体化合物，以及治疗与这些目标RNA分子相关疾病的方法。这些二聚体化合物还可以用于选择性地检测样本中目标RNA分子的存在。
• Novel compounds for the management of aging-related and diabetic vascular complications, process for their preparation, therapeutic and cosmetic uses thereof
  申请人：TORRENT PHARMACEUTICALS LTD.

  公开号：US20030045554A1

  公开（公告）日：2003-03-06

  The invention discloses a new clause of a five membered heterocylic ring compounds of general formula 1 1 and its pharmaceutically or cosmetically acceptable salts, wherein R1, R2, R3, R4, R5, A, B, X and Y are as defined in the specification. The invention also discloses a process for preparation of these compound and their therapeutic and cosmetic applications particularly in the management of aging related and diabetic vascular complications. The compounds in question act by triple action of an AGE (Advanced Glycation Endproducts) breaker, AGE inhibitor and free radical scavenger which make them most suitable in different therapeutic and cosmetic applications. The invention also discloses pharmaceuticals and cosmetic compositions comprising these compounds and method of treatment of diseases caused by accumulation of AGE and/or free radicals in the body cells.

  本发明公开了一种新的通式11的五元杂环化合物及其药学或美容学可接受的盐，其中R1、R2、R3、R4、R5、A、B、X和Y在说明书中定义。本发明还公开了制备这些化合物及其治疗和美容应用的方法，特别是在管理与衰老相关和糖尿病血管并发症方面。所述化合物通过AGE（高级糖基化终产物）断裂剂、AGE抑制剂和自由基清除剂的三重作用发挥作用，使它们在不同的治疗和美容应用中最为适用。本发明还公开了包含这些化合物的药物和化妆品组合物以及治疗由体细胞中AGE和/或自由基积累引起的疾病的方法。
• Nouveaux dérivés de la quinoléine, leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant
  申请人：ROUSSEL-UCLAF

  公开号：EP0070767B1

  公开（公告）日：1985-04-10
• HETEROCYCLIC COMPOUNDS FOR AGING-RELATED AND DIABETIC VASCULAR COMPLICATIONS
  申请人：Torrent Pharmaceuticals Ltd

  公开号：EP1373263B1

  公开（公告）日：2004-10-27
• SWEET FLAVOR MODIFIER
  申请人：Senomyx, Inc.

  公开号：EP2552207A1

  公开（公告）日：2013-02-06