甲基(4-硝基苯基)氨基甲酸叔丁酯 | 474020-88-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲基(4-硝基苯基)氨基甲酸叔丁酯
• 英文名称: tert‐butyl methyl(4‐nitrophenyl)carbamate
• 英文别名: tert-butyl methyl(4-nitrophenyl)carbamate；Tert-butyl N-methyl-N-(4-nitrophenyl)carbamate
• CAS: 474020-88-7
• 化学式: C₁₂H₁₆N₂O₄
• 分子量: 252.27
• InChiKey: FKIOMBZTRAZEBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  甲基(4-硝基苯基)氨基甲酸叔丁酯 在 盐酸 、 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 为溶剂， 反应 25.25h， 生成 尼达尼布
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.58h， 生成 甲基(4-硝基苯基)氨基甲酸叔丁酯
  参考文献：
  名称：

  N-alkyl-hydroxybenzoyl anilide hydroxamates as dual inhibitors of HDAC and HSP90, downregulating IFN-γ induced PD-L1 expression

  摘要：

  Novel dual inhibitors of histone deacetylase (HDAC) and heat-shock protein 90 (HSP90) are synthesized and evaluated. These compounds are endowed with potent HDAC and HSP90 inhibitory activities with IC50 values in nanomolar range with Compound 20 (HDAC IC50 =194 nM: HSP90ce IC50 =153 nM) and compound 26 (HDAC IC50- 360 nM; HSP90 alpha IC50 W 77 nM) displaying most potent HDAC and HSP90a inhibitory activities. Both of these compounds induce HSP70 expression and down regulate HSP90 client proteins which play important roles in the regulation of survival and invasiveness in cancer cells. In addition, compounds 20 and 26 induce acetylation of alpha-tubulin and histone H3. Significantly, compounds 20 and 26 could effectively reduce programmed death-ligand 1 (PD-L1) expression in IFN-gamma treated lung H1975 cells in a dose dependent manner. These findings suggest that dual inhibition of HDAC and HSP90 that can modulate immunosuppressive ability of tumor area may provide a better therapeutic strategy for cancer treatment in the future. (C) 2019 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111725

文献信息

• Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates
  作者：So Won Youn、Yi Hyun Kim

  DOI：10.1021/acs.orglett.6b03151

  日期：2016.12.2

  A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C–H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C–N bonds. A mechanism involving

  已经开发出一种简单且容易的一锅反应，以提供包含两个不同取代的N原子的N，N'-二取代的苯并咪唑酮和咪唑并吡啶并酮的不同范围。协同的Pd（II）/ Ag（I）系统促进了（杂）芳族胺和异氰酸酯的顺序加成/分子内CH-H酰胺化反应，导致形成两个C-N键。一种机制，涉及在Ag 2 CO 3氧化剂和Pd（OAc）2存在下通过单电子转移（SET）生成的自由基中间体提出了路易斯酸。该协议使用易于获得的起始原料，良好的官能团耐受性和高效率，提供了一种操作简便，简单且可靠的方法。
• Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
  作者：Oscar R. Suárez-Castillo、Luis Alberto Montiel-Ortega、Myriam Meléndez-Rodríguez、Maricruz Sánchez-Zavala

  DOI：10.1016/j.tetlet.2006.11.024

  日期：2007.1

  An efficient, simple protocol for the selective cleavage of a variety of N-alkoxycarbonyl protecting groups by t-BuNH2/MeOH is described. The scope of the procedure was explored for a series of indole, aniline and pyrrolidine carbamate derivatives containing other potentially reactive functional groups affording a clean cleavage of the carbamate group.

  描述了一种有效，简单的方案，用于通过t -BuNH 2 / MeOH选择性裂解各种N-烷氧基羰基保护基。探索了该程序的范围，以研究一系列含有其他潜在反应性官能团的吲哚，苯胺和吡咯烷氨基甲酸酯衍生物，从而提供了氨基甲酸酯基团的清晰裂解。
• Protein Kinase Conjugates and Inhibitors
  申请人：Celgene Avilomics Research, Inc.

  公开号：US20170174691A1

  公开（公告）日：2017-06-22

  The invention relates to protein conjugates that contain a protein kinase containing a cysteine residue in the ATP binding site and an inhibitor that is covalently and irreversibly bonded to said cysteine residue, such that the activity of the protein kinase is irreversibly inhibited. The invention also relates to compounds that irreversibly inhibit protein kinases.

  该发明涉及含有蛋白激酶的蛋白共轭物，该蛋白激酶在ATP结合位点含有半胱氨酸残基，并且与该半胱氨酸残基共价且不可逆地结合的抑制剂，从而不可逆地抑制了蛋白激酶的活性。该发明还涉及不可逆地抑制蛋白激酶的化合物。
• Design, synthesis and preliminary pharmacological evaluation of new analogues of DM232 (unifiram) and DM235 (sunifiram) as cognition modulators
  作者：Elisabetta Martini、Monica Norcini、Carla Ghelardini、Dina Manetti、Silvia Dei、Luca Guandalini、Michele Melchiorre、Simona Pagella、Serena Scapecchi、Elisabetta Teodori、Maria Novella Romanelli

  DOI：10.1016/j.bmc.2008.10.017

  日期：2008.12

  A series of amides, structurally related to DM232 (unifiram) and DM235 (sunifiram), characterized by a 1,2,3,4-tetrahydropyrazino[2,1-a]isoindol-6(2H)-one, 1,4-diamino-cyclohexane or 1,4-diaminobenzene ring, have been synthesized and tested for cognition-enhancing activity in the mouse passive-avoidance test. Some of the compounds display good antiamnesic and procognitive activity, with higher potency

  在结构上与DM232（unifiram）和DM235（sunifiram）有关的一系列酰胺，其特征在于1,2,3,4-四氢吡嗪并[2,1-a] isoindol-6（2H）-one，1,4-已经合成了二氨基环己烷或1,4-二氨基苯环，并在小鼠被动回避测试中测试了其增强认知的能力。一些化合物显示出良好的抗记忆和认知活性，并且比吡乙酰胺具有更高的效能，而某些环己烷衍生物具有诱发失忆的特性。
• [EN] UREA SUBSTITUTED SULPHONAMIDE DERIVATIVES<br/>[FR] DERIVES DE SULFONAMIDE SUBSTITUES PAR UREE
  申请人：BIOTIE THERAPIES CORP

  公开号：WO2010146236A1

  公开（公告）日：2010-12-23

  The present invention relates to sulphonamide derivatives, whith a urea moiety. The invention also relates to the use of the derivatives as inhibitors of collagen receptor integrins, especially α2β1 integrin inhibitors e.g. in connection with diseases and medical conditions that involve the action of cells and platelets expressing collagen receptors, their use as a medicament, e.g. for the treatment of thrombosis, inflammation, cancer and vascular diseases, pharmaceutical compositions containing them and a process for preparing them. The sulphonamide derivatives have the general formula (I) or (I').

  本发明涉及含有脲基的磺胺类衍生物。该发明还涉及将这些衍生物用作胶原受体整合素的抑制剂，特别是α2β1整合素抑制剂，例如在涉及表达胶原受体的细胞和血小板的疾病和医疗状况中使用，其用作药物，例如用于治疗血栓形成、炎症、癌症和血管疾病，含有它们的药物组合物以及制备它们的方法。这些磺胺类衍生物具有一般式(I)或(I')。