(R)-phenylcarbamoyloxy-phenyl-acetic acid ethyl ester

• 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: (R)-phenylcarbamoyloxy-phenyl-acetic acid ethyl ester
• 英文别名: (R)-Phenylcarbamoyloxy-phenyl-essigsaeure-aethylester；ethyl (2R)-2-phenyl-2-(phenylcarbamoyloxy)acetate
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: SSBAFSFBCZREQA-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  D-(-)-扁桃酸乙酯 、 异氰酸苯酯 生成 (R)-phenylcarbamoyloxy-phenyl-acetic acid ethyl ester
  参考文献：
  名称：

  Central and peripheral glucocorticoid receptor function in abdominal obesity

  摘要：

  Abdominal obesity seems to be associated with a moderately deranged feedback regulation of the hypothalamic-pituitary-ad renal (HPA) axis where central glucocorticoid receptors (GR) are involved. Therefore, functions of central and peripheral GR were compared in this study. Furthermore, since trinucleotide repeats in early exons of steroid hormone receptor genes influence transcription, and therefore may influence receptor density, this was also studied. Ten middle-aged men, 5 with abdominal obesity and 5 controls, were studied. The suppression of dexamethasone (dex) on serum cortisol was used in dose-response tests to assess the function of central GR. Abdominal adipose tissue biopsies were incubated and exposed to cortisol in different concentrations, and the function of the peripheral GR assayed as induction of lipoprotein lipase (LPL) activity. Aberrant expansion of exonic trinucleotide repeats in the first coding exon of the GR gene was studied by sequencing of genomic DNA. Results showed that men with abdominal obesity showed less inhibition of serum cortisol by dex, particularly at lower concentrations, while in the controls cortisol secretion was inhibited in an apparent dose-response manner. LPL activity in adipose tissue was lower in abdominal obese men than in controls. However, the sensitivity to cortisol was not different between the groups. There was no evidence for expansion of trinucleotide repeats. These results suggest that the central GR and the peripheral GR in adipose tissue exhibit functional differences in abdominal obesity.

  DOI：

  10.1007/bf03343995

文献信息

• Central and peripheral glucocorticoid receptor function in abdominal obesity
  作者：T. Ljung、M. Ottosson、A. C. Ahlberg、S. Edén、B. Odén、S. Okret、M. Brönnegård、P. Stierna、P. Björntorp

  DOI：10.1007/bf03343995

  日期：2002.3

  Abdominal obesity seems to be associated with a moderately deranged feedback regulation of the hypothalamic-pituitary-ad renal (HPA) axis where central glucocorticoid receptors (GR) are involved. Therefore, functions of central and peripheral GR were compared in this study. Furthermore, since trinucleotide repeats in early exons of steroid hormone receptor genes influence transcription, and therefore may influence receptor density, this was also studied. Ten middle-aged men, 5 with abdominal obesity and 5 controls, were studied. The suppression of dexamethasone (dex) on serum cortisol was used in dose-response tests to assess the function of central GR. Abdominal adipose tissue biopsies were incubated and exposed to cortisol in different concentrations, and the function of the peripheral GR assayed as induction of lipoprotein lipase (LPL) activity. Aberrant expansion of exonic trinucleotide repeats in the first coding exon of the GR gene was studied by sequencing of genomic DNA. Results showed that men with abdominal obesity showed less inhibition of serum cortisol by dex, particularly at lower concentrations, while in the controls cortisol secretion was inhibited in an apparent dose-response manner. LPL activity in adipose tissue was lower in abdominal obese men than in controls. However, the sensitivity to cortisol was not different between the groups. There was no evidence for expansion of trinucleotide repeats. These results suggest that the central GR and the peripheral GR in adipose tissue exhibit functional differences in abdominal obesity.