3-(2-methoxyethoxymethyl)benzylic alcohol | 219502-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-methoxyethoxymethyl)benzylic alcohol
• 英文别名: [3-(2-Methoxy-ethoxymethoxy)-phenyl]-methanol；[3-(2-methoxyethoxymethoxy)phenyl]methanol
• CAS: 219502-39-3
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: BBHQVXKRKNSJRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methoxyethoxymethyl)benzylic alcohol 在 四氯化碳 、 三苯基膦 作用下， 反应 3.0h， 以20%的产率得到3-(2-methoxyethoxymethyl)benzyl chloride
  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 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以95%的产率得到3-(2-methoxyethoxymethyl)benzylic alcohol
  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

文献信息

• Therapeutic uses of tri-aryl acid derivatives
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US07005440B1

  公开（公告）日：2006-02-28

  The use of triaryl acid derivatives of formula (I) and their pharmaceutical compositions as PPAR ligand receptor binders. The PPAR ligand receptor binders of this invention are useful as agonists or antagonists of the PPAR receptor.

  本发明涉及使用式(I)的三芳基酸衍生物及其制药组合物作为PPAR配体受体结合物。本发明的PPAR配体受体结合物可用作PPAR受体的激动剂或拮抗剂。
• TRI-ARYL ACID DERIVATIVES AS PPAR RECEPTOR LIGANDS
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1177176A1

  公开（公告）日：2002-02-06
• US7005440B1
  申请人：——

  公开号：US7005440B1

  公开（公告）日：2006-02-28
• [EN] TRI-ARYL ACID DERIVATIVES AS PPAR RECEPTOR LIGANDS<br/>[FR] DERIVES D'ACIDE TRI-ARYLE EN TANT QUE LIGANDS POUR RECEPTEUR DE PEROXISOME A ACTIVATION PAR PROLIFERATEUR (PPAR)
  申请人：AVENTIS PHARM PROD INC

  公开号：WO2000064876A1

  公开（公告）日：2000-11-02

  This invention is directed to triaryl acid derivatives of formula (I) and their pharmaceutical compositions as PPAR ligand receptor binders. The PPAR ligand receptor binders of this invention are useful as agonists or antagonists of the PPAR receptor. In formula (I), (a), (b), and (c) are independently aryl, fused arylcycloalkenyl, fused arylcycloalkyl, fused arylheterocyclenyl, fused arylheterocyclyl, heteroaryl, fused heteroarylcycloalkemyl, fused heteroarylcycloalkyl, fused heteroarylheterocyclenyl, or fused heteroarylheterocyclyl; A is -O-, -S-, -SO-, -SO2-, -NR13-, -C(O)-, -N(R14)C(O)-, -C(O)N(R15)-, -N(R14)C(O)N(R15)-, -C(R14)=N-, (d), (e), (f) a chemical bond, (g) or (h); B is -O-, -S-, -SO-, -SO2-, -NR17-, a chemical bond, ethynylene, -C(O)-, -N(R18)C(O)-, or -C(O)NR18-; D is -O-, -S-, -NR19-, a chemical bond, ethynylene, -C(O)-, -N(R20)C(O)-, or -C(O)N(R20)-; E is a chemical bond or an ethylene group; Z is R21O2C-, R21OC-, cyclo-imide, -CN, R21O2SHNCO-, R21O2SHN-, (R21)2NCO-, R21O-2,4-thiazolidinedionyl, or tetrazolyl.
• De Novo Design, Synthesis, and Biological Activities of High-Affinity and Selective Non-Peptide Agonists of the δ-Opioid Receptor
  作者：Subo Liao、Josue Alfaro-Lopez、Mark D. Shenderovich、Keiko Hosohata、Jun Lin、Xiaoping Li、Dagmar Stropova、Peg Davis、Kevin A. Jernigan、Frank Porreca、Henry I. Yamamura、Victor J. Hruby

  DOI：10.1021/jm980374r

  日期：1998.11.1

  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.