trifluoromethanesulfonic acid 4-(4-isopropoxy-3-isopropylbenzyl)-3,5-dimethylphenyl ester | 853201-44-2

• 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: trifluoromethanesulfonic acid 4-(4-isopropoxy-3-isopropylbenzyl)-3,5-dimethylphenyl ester
• CAS: 853201-44-2
• 化学式: C₂₂H₂₇F₃O₄S
• 分子量: 444.515
• InChiKey: NFGLOJFGQUTHIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 4-(4-isopropoxy-3-isopropylbenzyl)-3,5-dimethylphenyl ester 在 copper(l) iodide 、 四(三苯基膦)钯 、 三氯化铝 、 sodium azide 、 三乙胺盐酸盐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 YS-1
  参考文献：
  名称：

  Design and synthesis of complementing ligands for mutant thyroid hormone receptor TRβ(R320H): a tailor-made approach toward the treatment of resistance to thyroid hormone

  摘要：

  The thyroid hormone receptors (TR) are ligand-dependant transcription factors that regulate key genes involved in metabolic regulation, thermogenesis and development. Resistance to thyroid hormone (RTH) is a genetic disease associated with mutations to TR beta that lack or show reduced responsiveness to thyroid hormone (triiodothyronine). Previously we reported that the neutral alcohol-based thyromimetic HY-1 can selectively restore activity to a functionally impaired form of TR associated with RTH without over-stimulating TR alpha, which has been associated with undesirable side effects. Two new series of tetrazole and thiazolidinedione based ligands were evaluated for their ability to recover potency and efficacy to three of the most common RTH-associated mutants, TR beta(R320C), TR beta(R320H), and TR beta(R316H), in cell based assays. A new thiazolidinedione based ligand AH-9 was identified, which has near wild-type potency (EC50 = 0.54 nM) to TR beta(R320C) and TR beta(R320H). Significantly, AH-9 is equipotent toward TR alpha(wt), TR beta(wt), TR beta(R320C), and TR (RKOH), suggesting that AH-9 may have the potential to restore the normal homeostatic balance of thyroid hormone actions in patients or models harboring these mutations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.040
• 作为产物：
  描述：

  、 4-硝基苯酚三氟甲基磺酸酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以98%的产率得到trifluoromethanesulfonic acid 4-(4-isopropoxy-3-isopropylbenzyl)-3,5-dimethylphenyl ester
  参考文献：
  名称：

  Design and synthesis of complementing ligands for mutant thyroid hormone receptor TRβ(R320H): a tailor-made approach toward the treatment of resistance to thyroid hormone

  摘要：

  The thyroid hormone receptors (TR) are ligand-dependant transcription factors that regulate key genes involved in metabolic regulation, thermogenesis and development. Resistance to thyroid hormone (RTH) is a genetic disease associated with mutations to TR beta that lack or show reduced responsiveness to thyroid hormone (triiodothyronine). Previously we reported that the neutral alcohol-based thyromimetic HY-1 can selectively restore activity to a functionally impaired form of TR associated with RTH without over-stimulating TR alpha, which has been associated with undesirable side effects. Two new series of tetrazole and thiazolidinedione based ligands were evaluated for their ability to recover potency and efficacy to three of the most common RTH-associated mutants, TR beta(R320C), TR beta(R320H), and TR beta(R316H), in cell based assays. A new thiazolidinedione based ligand AH-9 was identified, which has near wild-type potency (EC50 = 0.54 nM) to TR beta(R320C) and TR beta(R320H). Significantly, AH-9 is equipotent toward TR alpha(wt), TR beta(wt), TR beta(R320C), and TR (RKOH), suggesting that AH-9 may have the potential to restore the normal homeostatic balance of thyroid hormone actions in patients or models harboring these mutations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.040