methyl 4-[5-[7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-yl]-1H-pyrrol-2-yl]benzoate | 1027398-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-[5-[7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-yl]-1H-pyrrol-2-yl]benzoate
• CAS: 1027398-46-4
• 化学式: C₂₁H₁₃F₄NO₃
• 分子量: 403.333
• InChiKey: JJPOTCZIOHVZEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  527.2±50.0 °C(predicted)
• 密度：
  1.386±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-[5-[7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-yl]-1H-pyrrol-2-yl]benzoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4-{5-[7-fluoro-4-(trifluoromethyl)benzo[b]furan-2-yl]-1H-2-pyrrolyl}benzoic acid
  参考文献：
  名称：

  Discovery of Novel and Potent Retinoic Acid Receptor α Agonists:  Syntheses and Evaluation of Benzofuranyl-pyrrole and Benzothiophenyl-pyrrole Derivatives

  摘要：

  In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of benzofuran and benzothiophene derivatives. Some of these compounds (1a,b,e,f,j) markedly inhibited LPS-induced B-lymphocyte proliferation and exerted RAR alpha selectivity. One of them, 4-[5-(4,7-dimethylbenzofuran-2-yl)pyrrol-2-yl]benzoic acid (1b), when orally administered significantly inhibited mouse antibody production and delayed type hypersensitivity (DTH) responses from a dose of 0.1 mg/kg.

  DOI：

  10.1021/jm000098s
• 作为产物：
  描述：

  2-氟-5-(三氟甲基)苯酚 在 吡啶 、 乙酸铵 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 偶氮二异丁腈 、 potassium tert-butylate 、 3-苄基羟乙基甲基噻唑氯化锂 、 potassium carbonate 、 二甲基亚砜 、 N,N-二甲基苯胺 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 61.42h， 生成 methyl 4-[5-[7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-yl]-1H-pyrrol-2-yl]benzoate
  参考文献：
  名称：

  Discovery of Novel and Potent Retinoic Acid Receptor α Agonists:  Syntheses and Evaluation of Benzofuranyl-pyrrole and Benzothiophenyl-pyrrole Derivatives

  摘要：

  In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of benzofuran and benzothiophene derivatives. Some of these compounds (1a,b,e,f,j) markedly inhibited LPS-induced B-lymphocyte proliferation and exerted RAR alpha selectivity. One of them, 4-[5-(4,7-dimethylbenzofuran-2-yl)pyrrol-2-yl]benzoic acid (1b), when orally administered significantly inhibited mouse antibody production and delayed type hypersensitivity (DTH) responses from a dose of 0.1 mg/kg.

  DOI：

  10.1021/jm000098s

文献信息

• Discovery of Novel and Potent Retinoic Acid Receptor α Agonists:  Syntheses and Evaluation of Benzofuranyl-pyrrole and Benzothiophenyl-pyrrole Derivatives
  作者：Hiroyuki Yoshimura、Kouichi Kikuchi、Shigeki Hibi、Katsuya Tagami、Takashi Satoh、Toshihiko Yamauchi、Akira Ishibahi、Kenji Tai、Takayuki Hida、Naoki Tokuhara、Mitsuo Nagai

  DOI：10.1021/jm000098s

  日期：2000.7.1

  In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of benzofuran and benzothiophene derivatives. Some of these compounds (1a,b,e,f,j) markedly inhibited LPS-induced B-lymphocyte proliferation and exerted RAR alpha selectivity. One of them, 4-[5-(4,7-dimethylbenzofuran-2-yl)pyrrol-2-yl]benzoic acid (1b), when orally administered significantly inhibited mouse antibody production and delayed type hypersensitivity (DTH) responses from a dose of 0.1 mg/kg.