(S)-3-(3-fluoro-4-methoxyphenyl)-2,2-dimethyl-3-phenylpropanoic acid | 1025475-88-0

• 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: (S)-3-(3-fluoro-4-methoxyphenyl)-2,2-dimethyl-3-phenylpropanoic acid
• 英文别名: (3S)-3-(3-fluoro-4-methoxyphenyl)-2,2-dimethyl-3-phenylpropanoic acid
• CAS: 1025475-88-0
• 化学式: C₁₈H₁₉FO₃
• 分子量: 302.345
• InChiKey: MNOQQLHBPFFAQW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-1,3,4-噻二唑 、 (S)-3-(3-fluoro-4-methoxyphenyl)-2,2-dimethyl-3-phenylpropanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 (S)-3-(3-fluoro-4-(methyloxy)phenyl)-2,2-dimethyl-3-phenyl-N-(1,3,4-thiadiazol-2-yl)propanamide
  参考文献：
  名称：

  Dimethyl-diphenyl-propanamide Derivatives As Nonsteroidal Dissociated Glucocorticoid Receptor Agonists

  摘要：

  A series of 2,2-dimethyl-3,3-diphenyl-propanamides as novel glucocorticoid receptor modulators is reported. SAR exploration led to the identification of 4-hydroxyphenyl propanamide derivatives displaying good agonist activity in GR-mediated transrepression assays and reduced agonist activity in GR-mediated transactivation assays. Compounds 17 and 30 showed anti-inflammatory activity comparable to prednisolone in the rat carrageenan-induced paw edema model, with markedly decreased side effects with regard to increases in blood glucose and expression of hepatic tyrosine aminotransferase. A hypothetical binding mode accounting for the induction of the functional activity by a 4-hydroxyl group is proposed.

  DOI：

  10.1021/jm100957a
• 作为产物：
  描述：

  3-(4-methoxy-3-fluorophenyl)-2,2-dimethyl-3-phenylpropanoic acid 在 Chiralpak-AD 作用下， 生成 (R)-3-(3-fluoro-4-methoxyphenyl)-2,2-dimethyl-3-phenylpropanoic acid 、 (S)-3-(3-fluoro-4-methoxyphenyl)-2,2-dimethyl-3-phenylpropanoic acid
  参考文献：
  名称：

  Dimethyl-diphenyl-propanamide Derivatives As Nonsteroidal Dissociated Glucocorticoid Receptor Agonists

  摘要：

  A series of 2,2-dimethyl-3,3-diphenyl-propanamides as novel glucocorticoid receptor modulators is reported. SAR exploration led to the identification of 4-hydroxyphenyl propanamide derivatives displaying good agonist activity in GR-mediated transrepression assays and reduced agonist activity in GR-mediated transactivation assays. Compounds 17 and 30 showed anti-inflammatory activity comparable to prednisolone in the rat carrageenan-induced paw edema model, with markedly decreased side effects with regard to increases in blood glucose and expression of hepatic tyrosine aminotransferase. A hypothetical binding mode accounting for the induction of the functional activity by a 4-hydroxyl group is proposed.

  DOI：

  10.1021/jm100957a

文献信息

• Dimethyl-diphenyl-propanamide Derivatives As Nonsteroidal Dissociated Glucocorticoid Receptor Agonists
  作者：Bingwei V. Yang、David S. Weinstein、Lidia M. Doweyko、Hua Gong、Wayne Vaccaro、Tram Huynh、Hai-yun Xiao、Arthur M. Doweyko、Lorraine Mckay、Deborah A. Holloway、John E. Somerville、Sium Habte、Mark Cunningham、Michele McMahon、Robert Townsend、David Shuster、John H. Dodd、Steven G. Nadler、Joel C. Barrish

  DOI：10.1021/jm100957a

  日期：2010.12.9

  A series of 2,2-dimethyl-3,3-diphenyl-propanamides as novel glucocorticoid receptor modulators is reported. SAR exploration led to the identification of 4-hydroxyphenyl propanamide derivatives displaying good agonist activity in GR-mediated transrepression assays and reduced agonist activity in GR-mediated transactivation assays. Compounds 17 and 30 showed anti-inflammatory activity comparable to prednisolone in the rat carrageenan-induced paw edema model, with markedly decreased side effects with regard to increases in blood glucose and expression of hepatic tyrosine aminotransferase. A hypothetical binding mode accounting for the induction of the functional activity by a 4-hydroxyl group is proposed.