Acetic acid 2-(2-methoxy-phenyl)-ethyl ester | 22532-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Acetic acid 2-(2-methoxy-phenyl)-ethyl ester
• 英文别名: 2-Methoxyphenethyl acetate；2-(2-methoxyphenyl)ethyl acetate
• CAS: 22532-50-9
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: RNFQYCSKLQMDKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid 2-(2-methoxy-phenyl)-ethyl ester 在 sodium hydroxide 、 三氯化铝 、 三(三氟乙酸)碘 、 铜 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 乙硫醇 为溶剂， 反应 1.0h， 生成 (S)-2-Amino-3-{4-[4-hydroxy-3-(2-hydroxy-ethyl)-phenoxy]-3,5-diiodo-phenyl}-propionic acid
  参考文献：
  名称：

  Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart

  摘要：

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.

  DOI：

  10.1021/jm00396a008
• 作为产物：
  描述：

  2-甲氧基苯乙酸 、 乙酰氯 生成 Acetic acid 2-(2-methoxy-phenyl)-ethyl ester
  参考文献：
  名称：

  El Zein,M. et al., Bulletin des Societes Chimiques Belges, 1978, vol. 87, p. 67 - 74

  摘要：

  DOI：

文献信息

• SCN9A antisense pain killer
  申请人：OliPass Corporation

  公开号：US11162104B2

  公开（公告）日：2021-11-02

  The current invention provides peptide nucleic acid derivatives targeting the 3′ splice site of exon 4 in the human SCN9A pre-mRNA. The peptide nucleic acid derivatives potently induce SCN9A mRNA splice variant(s) lacking the SCN9A exon 4 in cells, and are useful to safely treat pains or conditions involving Nav1.7 activity.

  本发明提供了靶向人 SCN9A 前 mRNA 第 4 外显子 3′剪接位点的多肽核酸衍生物。多肽核酸衍生物能有效诱导细胞中缺乏 SCN9A 第 4 号外显子的 SCN9A mRNA 剪接变体，可用于安全治疗涉及 Nav1.7 活性的疼痛或病症。
• EXON SKIPPING BY PEPTIDE NUCLEIC ACID DERIVATIVES
  申请人：OliPass Corporation

  公开号：US20190337987A1

  公开（公告）日：2019-11-07

  A peptide nucleic acid derivative of Formula I is provided to tightly bind to a splice site within a pre-mRNA in a sequence specific manner. Given with excellent cell membrane permeability and strong affinity for RNA, the said peptide nucleic acid derivative induces exon skipping in cells treated with the peptide nucleic acid at sub-femtomolar concentration as “naked” oligonucleotide. The said compound shows therapeutic activity in subjects upon systemic administration even at 1 μg/Kg or less, and therefore is useful to treat a disease or symptom at affordable treatment cost.
• ANDROGEN RECEPTOR ANTISENSE OLIGONUCLEOTIDES
  申请人：OliPass Corporation

  公开号：US20190345202A1

  公开（公告）日：2019-11-14

  Provided are peptide nucleic acid derivatives targeting the 5′ splice site of “exon 5” within the human androgen receptor pre-mRNA. The peptide nucleic acid derivatives potently induce splice variants of the androgen receptor mRNA in cells, and are useful to safely treat dermatological indications or conditions involving androgenic activity upon topical administration.
• [EN] HIF 1-ALPHA ANTISENSE OLIGONUCLEOTIDES<br/>[FR] OLIGONUCLÉOTIDES ANTISENS HIF 1-ALPHA
  申请人：OLIPASS CORP

  公开号：WO2018069764A1

  公开（公告）日：2018-04-19

  Provided are peptide nucleic acid derivatives targeting a part of the human HIF-1α pre-mRNA. The peptide nucleic acid derivatives potently induce exon skipping to yield splice variants of HIF-1α mRNA in cells, and are useful to treat indications or conditions involving the overexpression of HIF-1α.
• Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart
  作者：Paul D. Leeson、David Ellis、John C. Emmett、Virendra P. Shah、Graham A. Showell、Anthony H. Underwood

  DOI：10.1021/jm00396a008

  日期：1988.1

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.