tert-butyl benzyl(4-methylpyridin-2-yl)carbamate | 340042-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl benzyl(4-methylpyridin-2-yl)carbamate
• 英文别名: 2-(N-benzyl-N-Boc-amino)-4-methylpyridine；Tert-butyl N-benzyl-N-(4-methylpyridin-2-yl)carbamate
• CAS: 340042-24-2
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: UJAYXWVVKNEZJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  436.8±40.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl benzyl(4-methylpyridin-2-yl)carbamate 在 盐酸 、 氢溴酸 、 溴 、 sodium hexamethyldisilazane 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-(4-fluorophenyl)-3-[2-[(phenylmethyl)amino]4-pyridinyl]-imidazo[1,2-a]pyrimidin-7-amine
  参考文献：
  名称：

  Imidazopyrimidines, potent inhibitors of p38 MAP kinase

  摘要：

  The MAP kinase p38 is implicated in the release of the pro-inflammatory cytokines TNF-alpha and IL-1beta. Inhibition of cytokine release may be a useful treatment for inflammatory conditions such as rheumatoid arthritis and Crohn's disease. A novel series of imidazopyrimidines have been discovered that potently inhibit p38 and suppress the production of TNF-alpha in vivo. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01020-x
• 作为产物：
  描述：

  2-溴-4-甲基吡啶 在 tris(dibenzylideneacetone)dipalladium (0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 叔丁醇 为溶剂， 生成 tert-butyl benzyl(4-methylpyridin-2-yl)carbamate
  参考文献：
  名称：

  Imidazopyrimidines, potent inhibitors of p38 MAP kinase

  摘要：

  The MAP kinase p38 is implicated in the release of the pro-inflammatory cytokines TNF-alpha and IL-1beta. Inhibition of cytokine release may be a useful treatment for inflammatory conditions such as rheumatoid arthritis and Crohn's disease. A novel series of imidazopyrimidines have been discovered that potently inhibit p38 and suppress the production of TNF-alpha in vivo. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01020-x

文献信息

• KINASE MODULATORS FOR THE TREATMENT OF CANCER
  申请人：Synovo GmbH

  公开号：US20170313661A1

  公开（公告）日：2017-11-02

  A method of treating cancer in which a compound that inhibits the expression, production or release of IL-10 by immune cells is combined with a compound that stimulates the production of IL-12 when given in combination with, or in the presence of TNFa. Said method is effective when provided in addition to standard therapies, notably chemotherapy using cytotoxic drugs and other forms of immune therapy including therapeutic vaccines.

  一种治疗癌症的方法，其中抑制免疫细胞表达、产生或释放IL-10的化合物与在与TNFa联合给予或存在的情况下刺激IL-12产生的化合物结合。所述方法在提供标准疗法的基础上有效，特别是包括使用细胞毒性药物的化疗和其他形式的免疫疗法，包括治疗性疫苗。
• 2-SULFANYL-SUBSTITUTED IMIDAZOLE DERIVATIVES AND THEIR USE AS CYTOKINE INHIBITORS
  申请人：Burnet Michael

  公开号：US20090270462A1

  公开（公告）日：2009-10-29

  The invention relates to 2-thio-substituted imidazole derivatives of the Formula I, and to methods of use thereof.

  这项发明涉及到式I的2-硫代咪唑衍生物，以及其使用方法。
• Towards the improvement of the synthesis of novel 4(5)-aryl-5(4)-heteroaryl-2-thio-substituted imidazoles and their p38 MAP kinase inhibitory activity
  作者：Stefan Laufer、Pierre Koch

  DOI：10.1039/b717605h

  日期：——

  A series of 2-alkylsulfanyl-4-(4-fluorophenyl)-5-(2-aminopyridin-4-yl)-substituted imidazoles was prepared and interaction possibilities of the 2-thioether moiety with phosphate/ribose binding pockets of p38 MAP kinase were investigated. Introduction of the alkyl/benzyl amino function at the pyridine moiety was carried out via nucleophilic substitution or via palladium catalyzed aryl-C-N-bond formation

  制备了一系列的2-烷基硫烷基-4-（4-氟苯基）-5-（2-氨基吡啶-4-基）取代的咪唑，并且将2-硫醚部分与p38 MAP激酶的磷酸/核糖结合口袋相互作用的可能性被调查了。通过亲核取代或通过钯催化的芳基-CN-键形成在吡啶部分引入烷基/苄基氨基官能团。
• Synthesis of Unnatural α-Amino Acids from (Pyridin-2-yl) Carbamate via CIPE-Induced Carbonyl Migration
  作者：Juhui Wang、Aiwen Huo、Xiang Li、Yue Li、Yan Zhang、Tengda Jin、Keju Sun、Jingyue Yang

  DOI：10.1021/acs.joc.2c01283

  日期：2022.11.4

  Synthetic methods of unnatural α-amino acids have always been the focus of extensive research due to their significant bioactivities. However, convenient transition-metal-free catalyzed methods are still in demand. Herein, we report a novel strategy for the construction of an unnatural α-amino acid skeleton via intramolecular rearrangement of carbamates, which are readily available from amines and their

  非天然α-氨基酸的合成方法因其重要的生物活性一直是广泛研究的焦点。然而，仍然需要方便的无过渡金属催化方法。在此，我们报告了一种通过氨基甲酸酯的分子内重排构建非天然 α-氨基酸骨架的新策略，氨基甲酸酯很容易从胺及其常见的保护基中获得。即使在克级反应中，这种重排也能以高达 98% 的收率提供多种氨基酯产品。通过实验和理论计算对反应机理进行了详细研究。来自 2-吡啶基的复合物诱导邻近效应 (CIPE) 被证明对于这种转化是必不可少的。
• Targeting the Ribose and Phosphate Binding Site of p38 Mitogen-Activated Protein (MAP) Kinase: Synthesis and Biological Testing of 2-Alkylsulfanyl-, 4(5)-Aryl-, 5(4)-Heteroaryl-Substituted Imidazoles
  作者：Pierre Koch、Christiane Bäuerlein、Hartmut Jank、Stefan Laufer

  DOI：10.1021/jm800373t

  日期：2008.9.25

  Three series of substituted 2-alkylsulfanyl-4-(4-fluorophenyl)imidazoles, 5-pyridinyl-, 1-methyl-5-pyridinyl-, and 5-(2-aminopyridin-4-yl)-imidazoles, were prepared and tested for their ability to inhibit p38 MAP kinase and TNF-alpha release. These compounds were prepared by using different synthetic routes. They were tested by applying a nonradioactive p38 MAP kinase assay and by measurement of TNF-a release in human whole blood. Potent inhibitors (IC(50)values in the low nanomolar range, as low as 2 nM in the enzyme assay and 37 nM in the human whole blood test) were identified by variation of substituents at the imidazole-C2-thio position as well as at the 2-aminopyridinyl functionality. In contrast to other known kinase inhibitors, these novel imidazole derivatives with the substituents at the imidazole-C2-thio position may interact with the ribose as well as with the phosphate binding site of the p38 MAP kinase.