7-(benzyloxy)-1,2,3,4-tetrahydroquinoline

• 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: 7-(benzyloxy)-1,2,3,4-tetrahydroquinoline
• 英文别名: 7-(Benzyloxy)-1,2,3,4-tetrahydroquinoline；7-phenylmethoxy-1,2,3,4-tetrahydroquinoline
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: NFXLCQWSJCMLRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(benzyloxy)-1,2,3,4-tetrahydroquinoline 在 1,1'-bis(diphenylphosphino)ferrocine palladium(II) chloride potassium acetate 、 sodium carbonate 、 三乙胺 、 三氟乙酸 、 potassium iodide 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 95.17h， 生成 1-(3-methoxypropyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Discovery of 6-ethyl-2,4-diaminopyrimidine-based small molecule renin inhibitors

  摘要：

  Novel 2,4-diaminopyrimidine-based small molecule renin inhibitors are disclosed. Through high throughput screening, parallel synthesis, X-ray crystallography, and structure based drug design, we have developed the first non-chiral, non-peptidic, small molecular template to possess moderate potency against renin. The designed compounds consist of a novel 6-ethyl-5(1,2,3,4-tetrahydroquinolin-7-yl)pyrimidine-2,4-diamine ring system that exhibit moderate potency (IC50: 91-650 nM) against renin while remaining 'Rule-of-five' compliant. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.052
• 作为产物：
  描述：

  3,4-二氢-7-羟基-2(1H)-喹啉酮 在 硼烷四氢呋喃络合物 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 7-(benzyloxy)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  香豆素标记的乙烯基砜作为基于半肽模拟活性的半胱氨酸组织蛋白酶的探针

  摘要：

  三轮车光：通过聚合合成制备了包含刚性香豆素部分荧光基团的三肽模拟，乙烯基砜类基于活性的探针。该探针被评估为人类组织蛋白酶的灭活剂，并以组织蛋白酶S为例，证明适合在SDS-PAGE中成像。

  DOI：

  10.1002/cbic.201300806

文献信息

• A Coumarin-Labeled Vinyl Sulfone as Tripeptidomimetic Activity-Based Probe for Cysteine Cathepsins
  作者：Matthias D. Mertens、Janina Schmitz、Martin Horn、Norbert Furtmann、Jürgen Bajorath、Michael Mareš、Michael Gütschow

  DOI：10.1002/cbic.201300806

  日期：2014.5.5

  Tricycle light: A tripeptidomimetic, vinyl sulfone‐type activity‐based probe containing a rigid coumarin moiety fluorophore was prepared by convergent synthesis. The probe was evaluated as an inactivator of human cathepsins and, as exemplified with cathepsin S, it proved to be suitable for imaging in SDS‐PAGE.

  三轮车光：通过聚合合成制备了包含刚性香豆素部分荧光基团的三肽模拟，乙烯基砜类基于活性的探针。该探针被评估为人类组织蛋白酶的灭活剂，并以组织蛋白酶S为例，证明适合在SDS-PAGE中成像。
• Fluorescently Labeled Amino Acids as Building Blocks for Bioactive Molecules
  作者：Michael Gütschow、Daniela Häußler

  DOI：10.1055/s-0035-1560361

  日期：——

  A series of twelve fluorescently labeled amino acids were designed by assembling different coumarin, fluorescein, or nitrobenzofurazan fluorophores with N-protected lysine or 2-aminopropionic acid. The synthesized amino acids were evaluated with regard to their spectroscopic properties. The easy introduction of the amino acids into peptides and peptidomimetics was exemplarily shown for one coumarin-labeled amino acid.
• Discovery of 6-ethyl-2,4-diaminopyrimidine-based small molecule renin inhibitors
  作者：Daniel D. Holsworth、Mehran Jalaie、Thomas Belliotti、Cuiman Cai、Wendy Collard、Suzie Ferreira、Noel A. Powell、Michael Stier、Erli Zhang、Pat McConnell、Igor Mochalkin、Michael J. Ryan、John Bryant、Tingsheng Li、Aparna Kasani、Rajendra Subedi、Samarendra N. Maiti、Jeremy J. Edmunds

  DOI：10.1016/j.bmcl.2007.04.052

  日期：2007.7

  Novel 2,4-diaminopyrimidine-based small molecule renin inhibitors are disclosed. Through high throughput screening, parallel synthesis, X-ray crystallography, and structure based drug design, we have developed the first non-chiral, non-peptidic, small molecular template to possess moderate potency against renin. The designed compounds consist of a novel 6-ethyl-5(1,2,3,4-tetrahydroquinolin-7-yl)pyrimidine-2,4-diamine ring system that exhibit moderate potency (IC50: 91-650 nM) against renin while remaining 'Rule-of-five' compliant. (c) 2007 Elsevier Ltd. All rights reserved.
• Two Tags in One Probe: Combining Fluorescence‐ and Biotin‐based Detection of the Trypanosomal Cysteine Protease Rhodesain
  作者：Carina Lemke、Adéla Jílková、Dominic Ferber、Annett Braune、Anja On、Patrick Johe、Alena Zíková、Tanja Schirmeister、Michael Mareš、Martin Horn、Michael Gütschow

  DOI：10.1002/chem.202201636

  日期：2022.11.7

  A highly potent, bimodal activity-based probe for the therapeutically relevant cysteine protease rhodesain was developed. We utilized two different access points at the coumarin fluorophore for incorporation of the rhodesain inhibitor part and the biotin affinity label. The two reporter tags were employed for on-blot chemiluminescence detection and affinity purification as well as post-labeling quantification

  开发了一种针对治疗相关的半胱氨酸蛋白酶罗得红的高效、基于双峰活性的探针。我们在香豆素荧光团上使用了两个不同的接入点，用于掺入罗得红抑制剂部分和生物素亲和标记。这两个报告标签用于印迹化学发光检测和亲和纯化，以及通过尺寸排阻色谱和荧光检测对目标蛋白进行标记后定量。