3-[[7-[4-hydroxy-3-(3-phenylpropyl)phenoxy]-6-methyl-2,3-dihydro-1H-inden-4-yl]amino]-3-oxopropanoic acid | 575504-18-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-[[7-[4-hydroxy-3-(3-phenylpropyl)phenoxy]-6-methyl-2,3-dihydro-1H-inden-4-yl]amino]-3-oxopropanoic acid
• CAS: 575504-18-6
• 化学式: C₂₈H₂₉NO₅
• 分子量: 459.542
• InChiKey: IDVCKMBFGVTXCU-UHFFFAOYSA-N

物化性质

• 沸点：
  665.2±55.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl N-[7-(4-methoxyphenoxy)-6-methylindan-4-yl]malonamate 在 三乙基硅烷 、 三氟甲磺酸酐 、 水 、 三氯化硼 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 87.5h， 生成 3-[[7-[4-hydroxy-3-(3-phenylpropyl)phenoxy]-6-methyl-2,3-dihydro-1H-inden-4-yl]amino]-3-oxopropanoic acid
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationship (SAR) of N-[7-(4-hydroxyphenoxy)-6-methylindan-4-yl]malonamic acids as thyroid hormone receptor β (TRβ) selective agonists

  摘要：

  Highly TR beta selective thyromimetics have several potential therapeutic applications. Based on the novel indane derivative KTA-439 with high receptor (TR beta) and organ (liver) selectivity, a series of thyroid hormone analogues were prepared, in which the isopropyl at the 3'-position was replaced with alkyl and aralkyl moieties of variable lengths and branches. Binding assays for these human TRs and reporter cell assays showed that 2-arylethyl derivatives had higher TR beta selectivity than KTA-439. KTA-574, a representative 2-arylethyl derivative, had TR beta specificity in a binding assay and exhibited full agonism in a reporter cell assay. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.002

文献信息

• Design, synthesis, and structure–activity relationship (SAR) of N-[7-(4-hydroxyphenoxy)-6-methylindan-4-yl]malonamic acids as thyroid hormone receptor β (TRβ) selective agonists
  作者：Hiroaki Shiohara、Tetsuya Nakamura、Norihiko Kikuchi、Tomonaga Ozawa、Akane Matsuzawa、Ryuichi Nagano、Hideki Ohnota、Takahide Miyamoto、Kazuo Ichikawa、Kiyoshi Hashizume

  DOI：10.1016/j.bmc.2012.12.002

  日期：2013.2

  Highly TR beta selective thyromimetics have several potential therapeutic applications. Based on the novel indane derivative KTA-439 with high receptor (TR beta) and organ (liver) selectivity, a series of thyroid hormone analogues were prepared, in which the isopropyl at the 3'-position was replaced with alkyl and aralkyl moieties of variable lengths and branches. Binding assays for these human TRs and reporter cell assays showed that 2-arylethyl derivatives had higher TR beta selectivity than KTA-439. KTA-574, a representative 2-arylethyl derivative, had TR beta specificity in a binding assay and exhibited full agonism in a reporter cell assay. (C) 2012 Elsevier Ltd. All rights reserved.