N-[4'-(hydroxymethyl)biphenyl-3-yl]acetamide | 1268826-36-3

• 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: N-[4'-(hydroxymethyl)biphenyl-3-yl]acetamide
• 英文别名: N-[3-[4-(hydroxymethyl)phenyl]phenyl]acetamide
• CAS: 1268826-36-3
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: OTUWEFIQJKNZRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴苄醇 、 3-乙酰胺基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 150.0 ℃ 、1.5 MPa 条件下， 反应 0.42h， 以31%的产率得到N-[4'-(hydroxymethyl)biphenyl-3-yl]acetamide
  参考文献：
  名称：

  17β-HSD2 inhibitors for the treatment of osteoporosis: Identification of a promising scaffold

  摘要：

  17 beta-Hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) catalyses the conversion of active 17 beta-hydroxysteroids into the less active 17-ketosteroids thereby controlling the availability of biologically active estrogens (E2) and androgens (T) in the tissues. The skeletal disease osteoporosis occurs mainly in post-menopausal women and in elderly men when the levels of estrogens and androgens, respectively, decrease. Since 17 beta-HSD2 is present in osteoblasts, inhibition of this enzyme may provide a new and promising approach to prevent the onset of osteoporosis, keeping a certain level in estrogens and androgens in bone cells of ageing people. Hydroxynaphthyl, hydroxyphenyl and hydroxymethylphenyl-substituted moieties were synthesised as mimetics of the steroidal substrate. Compound 8 has been identified as promising scaffold for 17 beta-HSD2 inhibitors displaying high activity and good selectivity toward 17 beta-HSD1, ER alpha and ER beta. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.013

文献信息

• 17β-HSD2 inhibitors for the treatment of osteoporosis: Identification of a promising scaffold
  作者：Marie Wetzel、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1016/j.bmc.2010.12.013

  日期：2011.1

  17 beta-Hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) catalyses the conversion of active 17 beta-hydroxysteroids into the less active 17-ketosteroids thereby controlling the availability of biologically active estrogens (E2) and androgens (T) in the tissues. The skeletal disease osteoporosis occurs mainly in post-menopausal women and in elderly men when the levels of estrogens and androgens, respectively, decrease. Since 17 beta-HSD2 is present in osteoblasts, inhibition of this enzyme may provide a new and promising approach to prevent the onset of osteoporosis, keeping a certain level in estrogens and androgens in bone cells of ageing people. Hydroxynaphthyl, hydroxyphenyl and hydroxymethylphenyl-substituted moieties were synthesised as mimetics of the steroidal substrate. Compound 8 has been identified as promising scaffold for 17 beta-HSD2 inhibitors displaying high activity and good selectivity toward 17 beta-HSD1, ER alpha and ER beta. (C) 2010 Elsevier Ltd. All rights reserved.