8-tert-butyldimethylsilyloxy-2-methylquinoline | 171735-72-1

• 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: 8-tert-butyldimethylsilyloxy-2-methylquinoline
• 英文别名: 8-t-Butyldimethylsilyloxyquinaldine；tert-butyl-dimethyl-(2-methylquinolin-8-yl)oxysilane
• CAS: 171735-72-1
• 化学式: C₁₆H₂₃NOSi
• 分子量: 273.45
• InChiKey: QNAUHGLBSZTACN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-tert-butyldimethylsilyloxy-2-methylquinoline 在 selenium(IV) oxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 8-羟基喹啉-2-甲醛
  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
• 作为产物：
  描述：

  8-(Tert-butyldimethylsilanyloxy)-2-trifluoromethylquinoline 、 N-溴代丁二酰亚胺(NBS) 在 Disodium;sulfite 、 水 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以to give the product (21.4 g) as a dark oil的产率得到8-tert-butyldimethylsilyloxy-2-methylquinoline
  参考文献：
  名称：

  Heterocyclic compounds and their therapeutic use

  摘要：

  式(i)的N-氧化物，其中R1是CH3、CH2F、CHF2或CF3；R2是CH3或CF3；R3是F、Cl、Br、CN或CH3；R4是H、F、Cl、Br、CN或CH3；以及其药学上可接受的盐，可用作治疗剂，例如用于治疗炎症性疾病。

  公开号：

  US20010025049A1

文献信息

• Quinoline carboxanides and their therapeutic use
  申请人：Chiroscience Limited

  公开号：US05804588A1

  公开（公告）日：1998-09-08

  The subject invention concerns novel compounds of the general formula (i) ##STR1## that are useful in treating disease states, such as those states associated with proteins that mediate cellular activity. The compounds of the subject invention can be used, for example, to inhibit tumor necrosis factor and/or phosphodiesterase IV, The subject invention also concerns methods for treating disease states using the compounds of the invention.

  本发明涉及一般式（i）的新化合物 ##STR1## 这些化合物在治疗疾病状态方面有用，例如与介导细胞活动的蛋白质相关的状态。本发明的化合物可以用于抑制肿瘤坏死因子和/或磷酸二酯酶IV，本发明还涉及使用该发明化合物治疗疾病状态的方法。
• A new strategy for highly selective fluorescent sensing of F− and Zn2+ with dual output modes
  作者：Yinyin Bao、Bin Liu、Fanfan Du、Jiao Tian、Hu Wang、Ruke Bai

  DOI：10.1039/c2jm16364k

  日期：——

  A new strategy for highly selective and sensitive detection of both F− and Zn2+ with dual output modes was developed, which is based on a combination of F− induced desilylation reaction and chelation-enhanced fluorescence effect caused by Zn2+.

  我们开发了一种新的策略，通过结合F⁻诱导脱硅反应和Zn2+引起的螯合增强荧光效应，以双输出模式对F⁻和Zn2+进行高选择性、高灵敏度的检测。
• A “naked eye” and ratiometric fluorescent chemosensor for rapid detection of F− based on combination of desilylation reaction and excited-state proton transfer
  作者：Yinyin Bao、Bin Liu、Hu Wang、Jiao Tian、Ruke Bai

  DOI：10.1039/c1cc00034a

  日期：——

  A colorimetric and ratiometric fluorescent chemosensor for F(-) has been prepared, which is based on combination of desilylation reaction and excited-state proton transfer from the desilylation product to F(-). The sensor exhibits rapid response, excellent selectivity and sensitivity to F(-).

  基于去甲硅烷基化反应和从去甲硅烷基化产物到F（-）的激发态质子转移的结合，制备了用于F（-）的比色和比例荧光化学传感器。该传感器表现出快速响应，出色的选择性和对F（-）的灵敏度。
• Synthesis and Reactivity of Phosphine-Quinolinolato Rhodium Complexes: Intermediacy of Vinylidene and (Amino)carbene Complexes in the Catalytic Hydroamination of Terminal Alkynes
  作者：Shotaro Takano、Takuya Kochi、Fumitoshi Kakiuchi

  DOI：10.1021/acs.organomet.6b00853

  日期：2016.12.27

  We report here on the syntheses of rhodium(I) complexes bearing a phosphine-quinolinolate ligand and the isolation of two classes of important intermediates in the anti-Markovnikov hydroamination of terminal alkynes with secondary amines: vinylidene-bridged dirhodium complexes and (amino)carbene complexes. We first prepared various rhodium(I) complexes bearing a phosphine-quinolinolate ligand and found that some of these complexes had catalytic activity for the anti-Markovnikov hydroamination of terminal alkynes with secondary amines. The reaction of stoichiometric amounts of a (PNO)Rh complex with terminal alkynes provided vinylidene-bridged dirhodium complexes. When the resulting vinylidene complexes were reacted with secondary amines, (amino)carbene complexes were generated, which gave the hydroamination product upon heating with an additive. These results suggest that this anti-Markovnikov hydroamination catalyzed by (PNO)Rh complexes proceeds via vinylidene and (amino)carbene complexes.
• Asymmetric Synthesis of a New 8-Hydroxyquinoline-Derived α-Amino Acid and Its Incorporation in a Peptidylsensor for Divalent Zinc
  作者：Nathalie Jotterand、Dierdre A. Pearce、Barbara Imperiali

  DOI：10.1021/jo001681j

  日期：2001.5.1