2-quinolinecarboxaldehyde, 8-[[(1,1-dimethylethyl)dimethylsilyl]oxy] | 1070896-53-5

• 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-quinolinecarboxaldehyde, 8-[[(1,1-dimethylethyl)dimethylsilyl]oxy]
• 英文别名: 8-((tert-butyldimethylsilyl)oxy)quinoline-2-carbaldehyde；8-(tert-butyldimethylsilyloxy)-2-formylquinoline；8-(tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde；8-[tert-butyl(dimethyl)silyl]oxyquinoline-2-carbaldehyde
• CAS: 1070896-53-5
• 化学式: C₁₆H₂₁NO₂Si
• 分子量: 287.434
• InChiKey: CNPFFMXVRDLWLN-UHFFFAOYSA-N

物化性质

• 沸点：
  368.2±22.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-quinolinecarboxaldehyde, 8-[[(1,1-dimethylethyl)dimethylsilyl]oxy] 在 palladium 10% on activated carbon N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 四丁基氟化铵 、 水 、 氢气 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.33h， 生成 8-(trans)-(3-fluoropiperidin-4-yloxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolone
  参考文献：
  名称：

  WO2008/124323

  摘要：

  公开号：
• 作为产物：
  描述：

  8-tert-butyldimethylsilyloxy-2-methylquinoline 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 2-quinolinecarboxaldehyde, 8-[[(1,1-dimethylethyl)dimethylsilyl]oxy]
  参考文献：
  名称：

  Polyaminoquinoline Iron Chelators for Vectorization of Antiproliferative Agents: Design, Synthesis, and Validation

  摘要：

  Iron chelation in tumoral cells has been reported as potentially useful during antitumoral treatment. Our aim was to develop new polyaminoquinoline iron chelators targeting tumoral cells. For this purpose, we designed, synthesized, and evaluated the biological activity of a new generation of iron chelators, which we named Quilamines, based on an 8-hydroxyquinoline (8-HQ) scaffold linked to linear polyamine vectors. These were designed to target tumor cells expressing an overactive polyamine transport system (PTS). A set of Quilamines bearing variable polyamine chains was designed and assessed for their ability to interact with iron. Quilamines were also screened for their cytostatic/cytotoxic effects and their selective uptake by the PTS in the CHO cell line. Our results show that both the 8-HQ moiety and the polyamine part participate in the iron coordination. HQ1-44, the most promising Quilamine identified, presents a homospermidine moiety and was shown to be highly taken up by the PTS and to display an efficient antiproliferative activity that occurred in the micromolar range. In addition, cytotoxicity was only observed at concentrations higher than 100 mu M. We also demonstrated the high complexation capacity of HQ1-44 with iron while much weaker complexes were formed with other cations, indicative of a high selectivity. We applied the density functional theory to study the binding energy and the electronic structure of prototypical iron(III)-Quilamine complexes. On the basis of these calculations, Quilamine HQ1-44 is a strong tridentate ligand for iron(III) especially in the form of a 1:2 complex.

  DOI：

  10.1021/bc300324c

文献信息

• [EN] TRIAZOLOPYRIDINE COMPOUNDS AS PIM KINASE INHIBITORS<br/>[FR] COMPOSÉS DE TRIAZOLOPYRIDINE COMME INHIBITEURS DES KINASES PIM
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2010022081A1

  公开（公告）日：2010-02-25

  Compounds of Formula (I): I in which B, R1, R1a, R2, R3, R4, R5, R6, R7, R10 and R11 have the meanings given in the specification, are receptor tyrosine inhibitors useful in the treatment of diseases mediated by PIM-1 and/or PIM-2 and/or PIM-3 kinases.

  公式(I)的化合物：I，其中B、R1、R1a、R2、R3、R4、R5、R6、R7、R10和R11的含义如说明书所述，是受体酪氨酸抑制剂，用于治疗由PIM-1和/或PIM-2和/或PIM-3激酶介导的疾病。
• [EN] NEW COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：CT NAC INVESTIGACIONES ONCOLOGICAS CNIO

  公开号：WO2013005057A1

  公开（公告）日：2013-01-10

  There is provided compounds of formula I,wherein R1 R2, X, R3, X1, X2, Xa, Xb, Xc, Xd, Xf, X9 and R4 have meanings given in the description (and which compounds are optionally substituted as indicated in the description), and pharmaceutically-acceptable esters, amides, solvates or salts thereof, which compounds are useful in the treatment of diseases in which inhibition of a protein or lipid kinase (e.g. a PIM family kinase, such as PIM-1, PIM-2 and/or PIM-3) is desired and/or required, and particularly in the treatment of cancer or a proliferative disease. There is also provided combinations comprising the compounds of formula I.

  提供了具有式I的化合物，其中R1、R2、X、R3、X1、X2、Xa、Xb、Xc、Xd、Xf、X9和R4的含义如描述中所示（并且这些化合物可以根据描述中所示进行选择性取代），以及其药学上可接受的酯、酰胺、溶剂合物或盐，这些化合物在治疗需要或期望抑制蛋白激酶或脂质激酶（例如PIM家族激酶，如PIM-1、PIM-2和/或PIM-3）的疾病中非常有用，特别是在癌症或增殖性疾病的治疗中。还提供了包含式I化合物的组合物。
• [EN] TRIAZOLOPYRIDINE COMPOUNDS AS PIM KINASE INHIBITORS<br/>[FR] COMPOSÉS TRIAZOLOPYRIDINE COMME INHIBITEURS DE LA PIM KINASE
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2010022076A1

  公开（公告）日：2010-02-25

  Compounds of Formula (I), in which A, B, R1, R1a, R2, R3, R4, R5, R6, and R7 have the meanings given in the specification, are receptor tyrosine inhibitors useful in the treatment of immune cell-associated diseases and disorders, such as inflammatory and autoimmune diseases.

  公式（I）的化合物，其中A、B、R1、R1a、R2、R3、R4、R5、R6和R7的含义如规范中所述，是在治疗免疫细胞相关疾病和紊乱方面有用的受体酪氨酸激酶抑制剂，例如炎症性和自身免疫疾病。
• Synthesis and evaluation of (E)-2-(acrylamido)cyclohex-1-enecarboxylic acid derivatives as HCA1, HCA2, and HCA3 receptor agonists
  作者：Olga Bobileva、Rasma Bokaldere、Vija Gailite、Ilze Kaula、Martins Ikaunieks、Gunars Duburs、Ramona Petrovska、Ilona Mandrika、Janis Klovins、Einars Loza

  DOI：10.1016/j.bmc.2014.05.011

  日期：2014.7

  hydroxyl-carboxylic acid (HCA) receptor HCA2 agonists. A series of novel aryl derivatives of 2-amidocyclohex-1-ene carboxylic acid that contained rigidity elements, such as an E-double bond, triple bond, and trans or cis-substituted cyclopropane rings, instead of the saturated ethane linker in the amide part of the molecules were designed and synthesized, and the derivatives’ potency for the activation of HCA1, HCA2

  2-（3-（萘-2-基）丙酰胺基）环己-1-烯羧酸及其6-羟基萘-2-基类似物是众所周知的羟基羧酸（HCA）受体HCA2激动剂。一系列2-酰胺基环己-1-烯羧酸的新型芳基衍生物，其中包含刚性元素，例如E-双键，三键以及反式或顺式设计并合成了取代的环丙烷环，而不是分子酰胺部分中的饱和乙烷接头，并利用3'-5'-环腺苷一磷酸来活化衍生物的HCA1，HCA2和HCA3受体的能力（评估了cAMP）分析。SAR研究表明，适当分子的硬化可以调节HCA2受体激活的效力和选择性。
• Preparation and Properties of 2-(9′-Carbazolyl)-3-(8″-hydroxy-2″-Quinolinyl)Acrylonitrile Derivatives
  作者：Peng-Fei Xu、Tahsin J. Chow、Richard Lin、Ta-Jung Lu

  DOI：10.1002/jccs.200300019

  日期：2003.2

  chromophore. The carbazole group is twisted along the N(9″)-C(2) bond away from the major plane with a large dihedral angle. The major conjugated chromphore was found to be responsible for the spectral properties of these compounds. Protonation of the quinoline in these compounds red-shifted their absorption bands substantially.

  标题化合物的 E 和 Z 异构体是通过 2-甲醛-8-烷氧基喹啉和 N-氰基甲基咔唑缩合，然后水解来合成的。3b-c 中的烷氧基保护基团可以在酸或碱中裂解生成 3a。所有化合物均呈现蓝/绿发光，可用作发光二极管制造中的发光材料。对 3a-E、3d-Z 和 4-Z 进行了晶体衍射分析，结果表明这些分子之间存在共同的结构特征。喹啉的环与丙烯腈的双键共面，形成主要的共轭生色团。咔唑基团沿着 N(9″)-C(2) 键以大的二面角远离主平面扭曲。发现主要的共轭发色团对这些化合物的光谱特性负责。这些化合物中喹啉的质子化使它们的吸收带显着红移。