N-(naphthalene-1-ylmethyl)-2-bromoacetamide | 256656-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(naphthalene-1-ylmethyl)-2-bromoacetamide
• 英文别名: 2-bromo-N-(naphthalen-1-ylmethyl)acetamide
• CAS: 256656-69-6
• 化学式: C₁₃H₁₂BrNO
• 分子量: 278.148
• InChiKey: MYKFTHXSIYUMTK-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C(Solv: ethanol (64-17-5))
• 沸点：
  477.5±38.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(naphthalene-1-ylmethyl)-2-bromoacetamide 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 Phosphoric acid benzyl ester 6-(2-(4-methoxy-phenyl)-5-{[(naphthalen-1-ylmethyl)-carbamoyl]-methyl}-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylcarbamoyl)-naphthalen-2-yl ester
  参考文献：
  名称：

  Discovery of Thioazepinone Ligands for Src SH2: From Non-specific to Specific Binding

  摘要：

  The structure-based design and synthesis of new thioazepinones as ligands for Src SH2 protein is presented. From benzothioazepinones, ligands with somewhat unspecific binding properties, simpler thioazepinones were designed, the best ones demonstrated nanomolar affinity for Src SH2. A few of these new ligands were crystallized with the protein and demonstrated a specific binding mode with the protein. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00386-9
• 作为产物：
  描述：

  溴乙酰氯 、 1-萘甲基胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(naphthalene-1-ylmethyl)-2-bromoacetamide
  参考文献：
  名称：

  通过点击化学抑制人 α-1,3-岩藻糖基转移酶的强效和高选择性抑制剂

  摘要：

  由于围绕糖基转移反应家族的固有障碍，岩藻糖基转移酶和糖基转移酶的强效抑制剂一直难以捉摸。底物亲和力弱和岩藻糖基转移酶催化效率低的问题通过招募额外的结合特征（在这种情况下为疏水相互作用）来产生高亲和力抑制剂 24，Ki = 62 nM 得到了抵消。该分子是从包含 85 种化合物的 GDP-三唑文库中鉴定出来的，这些化合物是通过 Cu(I) 催化的叠氮化物和乙炔反应物之间的 [2 + 3] 环加成反应产生的，然后在没有产物分离的情况下进行原位筛选。

  DOI：

  10.1021/ja0302836

文献信息

• Structure−Activity Relationships in the Binding of Chemically Derivatized CD4 to gp120 from Human Immunodeficiency Virus
  作者：Hui Xie、Danny Ng、Sergey N. Savinov、Barna Dey、Peter D. Kwong、Richard Wyatt、Amos B. Smith、Wayne A. Hendrickson

  DOI：10.1021/jm070564e

  日期：2007.10.1

  The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp 120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp 120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp 120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.
• A Potent and Highly Selective Inhibitor of Human α-1,3-Fucosyltransferase via Click Chemistry
  作者：Lac V. Lee、Michael L. Mitchell、Shih-Jung Huang、Valery V. Fokin、K. Barry Sharpless、Chi-Huey Wong

  DOI：10.1021/ja0302836

  日期：2003.8.1

  Potent inhibitors of fucosyltransferases, and glycosyltransferases in general, have been elusive due to the inherent barriers surrounding the family of glycosyltransfer reactions. The problems of weak substrate affinity and low catalytic proficiency of fucosyltransferase was offset by recruiting additional binding features, in this case hydrophobic interactions, to produce a high affinity inhibitor

  由于围绕糖基转移反应家族的固有障碍，岩藻糖基转移酶和糖基转移酶的强效抑制剂一直难以捉摸。底物亲和力弱和岩藻糖基转移酶催化效率低的问题通过招募额外的结合特征（在这种情况下为疏水相互作用）来产生高亲和力抑制剂 24，Ki = 62 nM 得到了抵消。该分子是从包含 85 种化合物的 GDP-三唑文库中鉴定出来的，这些化合物是通过 Cu(I) 催化的叠氮化物和乙炔反应物之间的 [2 + 3] 环加成反应产生的，然后在没有产物分离的情况下进行原位筛选。
• Discovery of Thioazepinone Ligands for Src SH2: From Non-specific to Specific Binding
  作者：Dominique Lesuisse、Pierre Deprez、Eva Albert、Tran Thien Duc、Benoit Sortais、Dominique Gofflo、Véronique Jean-Baptiste、Jean-Pierre Marquette、Bernard Schoot、Edoardo Sarubbi、Gudrun Lange、Pierre Broto、Eliane Mandine

  DOI：10.1016/s0960-894x(01)00386-9

  日期：2001.8

  The structure-based design and synthesis of new thioazepinones as ligands for Src SH2 protein is presented. From benzothioazepinones, ligands with somewhat unspecific binding properties, simpler thioazepinones were designed, the best ones demonstrated nanomolar affinity for Src SH2. A few of these new ligands were crystallized with the protein and demonstrated a specific binding mode with the protein. (C) 2001 Elsevier Science Ltd. All rights reserved.