1-chloro-1-<3-(2-methoxyethoxymethyl)phenyl>ethane | 219502-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-chloro-1-<3-(2-methoxyethoxymethyl)phenyl>ethane
• 英文别名: 1-(1-Chloroethyl)-3-(2-methoxyethoxymethoxy)benzene
• CAS: 219502-46-2
• 化学式: C₁₂H₁₇ClO₃
• 分子量: 244.718
• InChiKey: VBABAJSAEBJYRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-chloro-1-<3-(2-methoxyethoxymethyl)phenyl>ethane 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 26.0h， 生成 1-(3-hydroxy-α-methylbenzyl)-4-benzylpiperazine dihydrochloride
  参考文献：
  名称：

  De Novo Design, Synthesis, and Biological Activities of High-Affinity and Selective Non-Peptide Agonists of the δ-Opioid Receptor

  摘要：

  On the basis of the structure-activity relationships of delta-opioid-selective peptide ligands and on a model of the proposed bioactive conformation for a potent and selective, conformationally constrained delta-opioid peptide ligand [(2S,3R)-TMT1]DPDPE, a series of small organic peptide mimetic compounds targeted for the delta-opioid receptor have been designed, synthesized, and evaluated in radiolabeled ligand binding assays and in vitro bioassays. The new non-peptide ligands use piperazine as a template to present the most important pharmacophore groups, including phenol and phenyl groups and a hydrophobic moiety. This hydrophobic group was designed to mimic the hydrophobic character of the D-Pen residues in DPDPE, which has been found to be extremely important for increasing the binding affinity and selectivity of these non-peptide ligands for the delta-opioid receptor over the mu-opioid receptor. Compound 6f (SL-3111) showed 8 nM binding affinity and over 2000-fold selectivity for the delta-opioid receptor over the delta-opioid receptor. Both enantiomers of SL-3111 were separated, and the (-)-isomer was shown to be the compound with the highest affinity for the delta-opioid receptor found in our study (IC50 = 4.1 nM), with a selectivity very similar to that observed for the racemic compound. The phenol hydroxyl group of SL-3111 turned out to be essential to maintain high affinity for the delta-opioid receptor, which also was observed in the case of the delta-opioid-selective peptide ligand DPDPE. Binding studies of SL-3111 and [p-C1Phe(4)]DPDPE on the cloned wild-type and mutated human delta-opioid receptors suggested that the new non-peptide ligand has a binding profile similar to that of DPDPE but different from that of (+)-4-[((alpha R)-alpha(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl] -N,N-diethylbenzamide (SNC-80), another; delta-opioid-selective non-peptide ligand.

  DOI：

  10.1021/jm980374r
• 作为产物：
  描述：

  3-[(2-甲氧基乙氧基)甲氧基]苯甲醛 在 四氯化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1-chloro-1-<3-(2-methoxyethoxymethyl)phenyl>ethane
  参考文献：
  名称：

  De Novo Design, Synthesis, and Biological Activities of High-Affinity and Selective Non-Peptide Agonists of the δ-Opioid Receptor

  摘要：

  On the basis of the structure-activity relationships of delta-opioid-selective peptide ligands and on a model of the proposed bioactive conformation for a potent and selective, conformationally constrained delta-opioid peptide ligand [(2S,3R)-TMT1]DPDPE, a series of small organic peptide mimetic compounds targeted for the delta-opioid receptor have been designed, synthesized, and evaluated in radiolabeled ligand binding assays and in vitro bioassays. The new non-peptide ligands use piperazine as a template to present the most important pharmacophore groups, including phenol and phenyl groups and a hydrophobic moiety. This hydrophobic group was designed to mimic the hydrophobic character of the D-Pen residues in DPDPE, which has been found to be extremely important for increasing the binding affinity and selectivity of these non-peptide ligands for the delta-opioid receptor over the mu-opioid receptor. Compound 6f (SL-3111) showed 8 nM binding affinity and over 2000-fold selectivity for the delta-opioid receptor over the delta-opioid receptor. Both enantiomers of SL-3111 were separated, and the (-)-isomer was shown to be the compound with the highest affinity for the delta-opioid receptor found in our study (IC50 = 4.1 nM), with a selectivity very similar to that observed for the racemic compound. The phenol hydroxyl group of SL-3111 turned out to be essential to maintain high affinity for the delta-opioid receptor, which also was observed in the case of the delta-opioid-selective peptide ligand DPDPE. Binding studies of SL-3111 and [p-C1Phe(4)]DPDPE on the cloned wild-type and mutated human delta-opioid receptors suggested that the new non-peptide ligand has a binding profile similar to that of DPDPE but different from that of (+)-4-[((alpha R)-alpha(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl] -N,N-diethylbenzamide (SNC-80), another; delta-opioid-selective non-peptide ligand.

  DOI：

  10.1021/jm980374r