N-(2-benzylphenyl)-2-bromoacetamide | 748798-96-1

• 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: N-(2-benzylphenyl)-2-bromoacetamide
• CAS: 748798-96-1
• 化学式: C₁₅H₁₄BrNO
• mdl: MFCD19512069
• 分子量: 304.186
• InChiKey: XYMQUWBJEIFJGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  454.2±38.0 °C(Predicted)
• 密度：
  1.414±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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-(2-benzylphenyl)-2-bromoacetamide 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.0h， 生成 (2-Benzyl-phenyl)-(2-pyrrolidin-1-yl-ethyl)-amine
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 9. Oxygen-Containing Midsized Heterocyclic Ring Systems and Nonrigidized Analogues. A Step toward Dopamine D₅ Receptor Selectivity

  摘要：

  Eleven-membered heterocycles (dibenz[g,j]-1-oxa-4-azacycloundecenes) and open-chain analogues were synthesized and investigated for affinities to human dopamine receptor subtypes. The moderately rigidized rings displayed nanomolar and sulmanomolar K-i values at D-1-like receptors with a significant D-1 to D-2 and a slight D-5 to D-6 selectivity. The open-chain analogues showed lower affinities but significant D-1 to D-2 selectivities. Compound 3 (K-i(D-5) = 0.57 nmol) showed antagonistic or inverse agonistic binding characteristics in a functional Ca assay.

  DOI：

  10.1021/jm049720x
• 作为产物：
  描述：

  邻苄基苯胺 、 溴乙酰溴 以 乙醚 为溶剂， 反应 2.0h， 以50%的产率得到N-(2-benzylphenyl)-2-bromoacetamide
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 9. Oxygen-Containing Midsized Heterocyclic Ring Systems and Nonrigidized Analogues. A Step toward Dopamine D₅ Receptor Selectivity

  摘要：

  Eleven-membered heterocycles (dibenz[g,j]-1-oxa-4-azacycloundecenes) and open-chain analogues were synthesized and investigated for affinities to human dopamine receptor subtypes. The moderately rigidized rings displayed nanomolar and sulmanomolar K-i values at D-1-like receptors with a significant D-1 to D-2 and a slight D-5 to D-6 selectivity. The open-chain analogues showed lower affinities but significant D-1 to D-2 selectivities. Compound 3 (K-i(D-5) = 0.57 nmol) showed antagonistic or inverse agonistic binding characteristics in a functional Ca assay.

  DOI：

  10.1021/jm049720x

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.
• CN116178383
  申请人：——

  公开号：——

  公开（公告）日：——
• Dopamine/Serotonin Receptor Ligands. 9. Oxygen-Containing Midsized Heterocyclic Ring Systems and Nonrigidized Analogues. A Step toward Dopamine D₅ Receptor Selectivity
  作者：Thomas W. Wittig、Michael Decker、Jochen Lehmann

  DOI：10.1021/jm049720x

  日期：2004.8.1

  Eleven-membered heterocycles (dibenz[g,j]-1-oxa-4-azacycloundecenes) and open-chain analogues were synthesized and investigated for affinities to human dopamine receptor subtypes. The moderately rigidized rings displayed nanomolar and sulmanomolar K-i values at D-1-like receptors with a significant D-1 to D-2 and a slight D-5 to D-6 selectivity. The open-chain analogues showed lower affinities but significant D-1 to D-2 selectivities. Compound 3 (K-i(D-5) = 0.57 nmol) showed antagonistic or inverse agonistic binding characteristics in a functional Ca assay.