4-aminobenzylamino carbamate | 302923-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-aminobenzylamino carbamate
• 英文别名: allyl 4-aminobenzylaminocarbamate；allyl (4-aminobenzyl)carbamate；Prop-2-en-1-yl [(4-aminophenyl)methyl]carbamate；prop-2-enyl N-[(4-aminophenyl)methyl]carbamate
• CAS: 302923-29-1
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: ZGSAJVQUOSZZDC-UHFFFAOYSA-N

物化性质

• 沸点：
  384.3±35.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-aminobenzylamino carbamate 在 lithium hydroxide 、 TEA 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 36.0h， 生成 9-(4'-methylamino-allyloxycarbamate)anilinoacridine-4-carboxylic acid
  参考文献：
  名称：

  Solid-phase synthesis of acridine-based threading intercalator peptides

  摘要：

  The preparation of a novel acridine-based amino acid is reported. This N-Alloc-protected monomer call be coupled and deprotected under solid-phase peptide synthesis procedures to create acridine-peptide conjugates as potential threading intercalators. A peptide containing this novel amino acid undergoes spectral changes in the presence of duplex DNA and RNA consistent with intercalative binding. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00388-7
• 作为产物：
  描述：

  prop-2-enyl N-[(4-nitrophenyl)methyl]carbamate 在 copper acetylacetonate sodium tetrahydroborate 、 水 作用下， 以 乙醇 为溶剂， 反应 16.5h， 生成 4-aminobenzylamino carbamate
  参考文献：
  名称：

  [EN] BIPIPERIDINYL DERIVATIVES USEFUL AS INHIBITORS OF CHEMOKINE RECEPTORS
  [FR] DERIVES DE BIPIPERIDINYL UTILISES COMME INHIBITEURS DES RECEPTEURS DE CHEMOKINE

  摘要：

  公开号：

  WO2005042517A3

文献信息

• Design, Synthesis, and Biological Evaluation of Covalent Inhibitors of Focal Adhesion Kinase (FAK) against Human Malignant Glioblastoma
  作者：Bo Li、Yongliang Li、Céline Tomkiewicz-Raulet、Pascal Dao、Daniel Lietha、Expédite Yen-Pon、Zhiyun Du、Xavier Coumoul、Christiane Garbay、Mélanie Etheve-Quelquejeu、Huixiong Chen

  DOI：10.1021/acs.jmedchem.0c01059

  日期：2020.11.12

  integrin downstream signaling mediators in GBM such as focal adhesion kinase (FAK) seems reasonable and recently demonstrated promising results in early clinical studies. Herein, we report the structure-guided development of a series of covalent inhibitors of FAK. These new compounds displayed highly potent inhibitory potency against FAK enzymatic activity with IC50 values in the nanomolar range. Several

  人恶性胶质母细胞瘤（GBM）是一种高度侵袭性和致死性的脑肿瘤。针对GBM中整合素下游信号传导介质（如粘着斑激酶（FAK））的目标似乎是合理的，并且最近在早期临床研究中显示出令人鼓舞的结果。在这里，我们报告了一系列FAK的共价抑制剂的结构指导的发展。这些新化合物对IC 50表现出对FAK酶活性的强抑制力值在纳摩尔范围内。通过在多个人胶质母细胞瘤细胞系中的细胞活力测定评估，几种抑制剂可抑制肿瘤细胞的生长。他们还通过将细胞停在G2 / M期来显着降低U-87细胞迁移的速率并延迟了细胞周期进程。此外，这些抑制剂在胶质母细胞瘤细胞及其下游效应器Akt和Erk以及核因子-κB中显示出FAK的自磷酸化作用的有效降低。这些数据表明，这些抑制剂可能具有为人胶质母细胞瘤提供有希望的新靶向疗法的潜力。
• RNA binding and thiolytic stability of a quinoline-containing helix-threading peptide
  作者：Malathy Krishnamurthy、Barry D. Gooch、Peter A. Beal

  DOI：10.1039/b513591e

  日期：——

  Helix-threading peptides (HTPs) bind selectively to sites predisposed to intercalation in folded RNA molecules placing peptide functional groups into the dissimilar grooves of the duplex. Here we report the design and synthesis of new HTPs with quinoline as the intercalation domain. A quinoline-containing HTP is shown to bind selectively to duplex RNA binding sites. Furthermore, the affinity cleavage

  螺旋螺纹肽（HTP）选择性结合易折叠的RNA分子中易于插入的位点，从而将肽官能团置于双链体的不同凹槽中。在这里，我们报告了以喹啉为嵌入域的新型HTP的设计和合成。已显示含喹啉的HTP与双链体RNA结合位点选择性结合。此外，使用EDTA.Fe修饰的衍生物生成的亲和力裂解模式与其N末端的小沟定位相一致。该化合物结合两条链的3'侧的单核苷酸凸起侧翼的碱基对步骤，而插入位点5'侧的凸起不支持结合。此外，与a啶HTP不同，喹啉化合物具有抗硫解降解的能力，该降解导致RNA结合活性的丧失。
• Design, Synthesis, and Evaluation of Novel Imidazo[1,2-<i>a</i>][1,3,5]triazines and Their Derivatives as Focal Adhesion Kinase Inhibitors with Antitumor Activity
  作者：Pascal Dao、Nikaia Smith、Céline Tomkiewicz-Raulet、Expédite Yen-Pon、Marta Camacho-Artacho、Daniel Lietha、Jean-Phillipe Herbeuval、Xavier Coumoul、Christiane Garbay、Huixiong Chen

  DOI：10.1021/jm500784e

  日期：2015.1.8

  A series of triazinic inhibitors of focal adhesion kinase (FAK) have been recently shown to exert antiangiogenic activity against HUVEC cells and anticancer efficacy against several cancer cell lines. We report herein that we further explored the heterocyclic core of these inhibitors by a fused imidazole ring with the triazine to provide imidazo[1,2-a][1,3,5]triazines. Importantly, these new compounds displayed 10(-7-)10(-8) M IC50 values, and the best inhibitor showed IC50 value of 50 nM against FAK enzymatic activity. Several inhibitors potently inhibited the proliferation of a panel of cancer cell lines expressing high levels of FAK. Apoptosis analysis in U87-MG and HCT-116 cell lines suggested that these compounds delayed cell cycle progression by arresting cells in the G2/M phase of the cell cycle, retarding cell growth. Further investigation demonstrated that these compounds strongly inhibited cell-matrix adhesion, migration, and invasion of U87-MG cells.
• Peptide Quinoline Conjugates:  A New Class of RNA-Binding Molecules
  作者：Malathy Krishnamurthy、Barry D. Gooch、Peter A. Beal

  DOI：10.1021/ol036094+

  日期：2004.1.1

  A synthesis of 4,8-disubstituted 2-phenylquinoline amino acids is reported with the incorporation of one example into a peptide by solid-phase synthesis. The phenylquinoline-containing peptide binds an RNA target with nanomolar affinity (K-D = 208 nM). The strategy can be used to prepare a variety of 2-substituted quinoline amino acids for alteration of affinity in intercalator peptides. Since quinolones represent an important class of antibacterials, these compounds may be useful in the discovery of new antibacterial agents.
• US7652142B2
  申请人：——

  公开号：US7652142B2

  公开（公告）日：2010-01-26