3-(allyloxy)-4-fluorophenol | 448957-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(allyloxy)-4-fluorophenol
• 英文别名: 4-fluoro-3-prop-2-enoxyphenol
• CAS: 448957-15-1
• 化学式: C₉H₉FO₂
• 分子量: 168.168
• InChiKey: LQBHZBZJZRWNHC-UHFFFAOYSA-N

物化性质

• 沸点：
  278.8±25.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(allyloxy)-4-fluorophenol 在 四(三苯基膦)钯 、 偶氮二甲酸二叔丁酯 、 苯硅烷 、 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 ethyl (5-(4-(((2,4-difluorobenzyl)(2-methyl-3-nitrophenyl)amino)methyl)phenoxy)-2-fluorophenoxy)acetate
  参考文献：
  名称：

  Antidiabetic Activity of Passive Nonsteroidal Glucocorticoid Receptor Modulators

  摘要：

  Much has been learned about the consequences of glucocorticoid receptor antagonism by studying steroidal active antagonists such as RU-38486 (1). In the liver glucocorticoid receptor antagonism suppresses hepatic glucose production decreasing plasma glucose levels; however, extrahepatic antagonism produces several undesirable side effects including activation of the hypothalamic pituitary adrenal axis. A series of nonsteroidal passive N-(3-dibenzylamino-2-alkyl-phenyl)-methanesulfonamide glucocorticoid receptor modulators was discovered. Liver selective and systemically available members of this series were found and characterized in diabetes and side effect rodent models. A highly liver selective member of this series, acid 14, shows efficacy in the ob/ob model of diabetes. It lowers plasma glucose, cholesterol, and free fatty acid concentrations and reduces the rate of body weight gain. The structurally related systemically available passive modulator 12 lowers glucose, HbA(1c), triglyceride, free fatty acid, and cholesterol levels. Interestingly, it did not acutely activate the hypothalamic pituitary adrenal axis in unstressed CD-1 mice or have the abortive effects observed with 1. These results indicate that passive GR antagonists may have utility as antidiabetic agents.

  DOI：

  10.1021/jm050205o
• 作为产物：
  描述：

  4-氟间苯二酚 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 26.0h， 生成 3-(allyloxy)-4-fluorophenol
  参考文献：
  名称：

  Antidiabetic Activity of Passive Nonsteroidal Glucocorticoid Receptor Modulators

  摘要：

  Much has been learned about the consequences of glucocorticoid receptor antagonism by studying steroidal active antagonists such as RU-38486 (1). In the liver glucocorticoid receptor antagonism suppresses hepatic glucose production decreasing plasma glucose levels; however, extrahepatic antagonism produces several undesirable side effects including activation of the hypothalamic pituitary adrenal axis. A series of nonsteroidal passive N-(3-dibenzylamino-2-alkyl-phenyl)-methanesulfonamide glucocorticoid receptor modulators was discovered. Liver selective and systemically available members of this series were found and characterized in diabetes and side effect rodent models. A highly liver selective member of this series, acid 14, shows efficacy in the ob/ob model of diabetes. It lowers plasma glucose, cholesterol, and free fatty acid concentrations and reduces the rate of body weight gain. The structurally related systemically available passive modulator 12 lowers glucose, HbA(1c), triglyceride, free fatty acid, and cholesterol levels. Interestingly, it did not acutely activate the hypothalamic pituitary adrenal axis in unstressed CD-1 mice or have the abortive effects observed with 1. These results indicate that passive GR antagonists may have utility as antidiabetic agents.

  DOI：

  10.1021/jm050205o

文献信息

• Glucocorticoid receptor modulators
  申请人：——

  公开号：US20020156311A1

  公开（公告）日：2002-10-24

  Compounds of formula (I) 1 or pharmaceutically acceptable salts thereof are novel glucocorticoid receptor modulators and are useful for treating type II diabetes in a mammal.

  化合物的结构式（I）1或其药学上可接受的盐是新型糖皮质激素受体调节剂，可用于治疗哺乳动物的II型糖尿病。
• [EN] GLUCOCORTICOID RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RECEPTEURS DES GLUCOCORTICOIDES
  申请人：ABBOTT LAB

  公开号：WO2002064550A1

  公开（公告）日：2002-08-22

  Compounds of formula (I) (I), or pharmaceutically acceptable salts thereof are novel glucocorticoid receptor modulators and are useful for treating type II diabetes in a mammal.

  式(I)的化合物，或其药学上可接受的盐是一种新型糖皮质激素受体调节剂，可用于治疗哺乳动物的2型糖尿病。
• GLUCOCORTICOID RECEPTOR MODULATORS
  申请人：Abbott Laboratories

  公开号：EP1363876A1

  公开（公告）日：2003-11-26
• US6583180B2
  申请人：——

  公开号：US6583180B2

  公开（公告）日：2003-06-24
• Antidiabetic Activity of Passive Nonsteroidal Glucocorticoid Receptor Modulators
  作者：J. T. Link、Bryan Sorensen、Jyoti Patel、Marlena Grynfarb、Annika Goos-Nilsson、Jiahong Wang、Steven Fung、Denise Wilcox、Brad Zinker、Phong Nguyen、Bach Hickman、James M. Schmidt、Sue Swanson、Zhenping Tian、Thomas J. Reisch、Gary Rotert、Jia Du、Benjamin Lane、Thomas W. von Geldern、Peer B. Jacobson

  DOI：10.1021/jm050205o

  日期：2005.8.1

  Much has been learned about the consequences of glucocorticoid receptor antagonism by studying steroidal active antagonists such as RU-38486 (1). In the liver glucocorticoid receptor antagonism suppresses hepatic glucose production decreasing plasma glucose levels; however, extrahepatic antagonism produces several undesirable side effects including activation of the hypothalamic pituitary adrenal axis. A series of nonsteroidal passive N-(3-dibenzylamino-2-alkyl-phenyl)-methanesulfonamide glucocorticoid receptor modulators was discovered. Liver selective and systemically available members of this series were found and characterized in diabetes and side effect rodent models. A highly liver selective member of this series, acid 14, shows efficacy in the ob/ob model of diabetes. It lowers plasma glucose, cholesterol, and free fatty acid concentrations and reduces the rate of body weight gain. The structurally related systemically available passive modulator 12 lowers glucose, HbA(1c), triglyceride, free fatty acid, and cholesterol levels. Interestingly, it did not acutely activate the hypothalamic pituitary adrenal axis in unstressed CD-1 mice or have the abortive effects observed with 1. These results indicate that passive GR antagonists may have utility as antidiabetic agents.