6-Amino-3-hydroxymethyl-1-thiophen-2-yl-indan-5-ol | 339309-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-Amino-3-hydroxymethyl-1-thiophen-2-yl-indan-5-ol
• CAS: 339309-61-4
• 化学式: C₁₄H₁₅NO₂S
• 分子量: 261.345
• InChiKey: OJZBHWICPMBRTP-UHFFFAOYSA-N

物化性质

• 沸点：
  459.4±45.0 °C(predicted)
• 密度：
  1.364±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  异丁酸酐 、 6-Amino-3-hydroxymethyl-1-thiophen-2-yl-indan-5-ol 在 potassium carbonate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 20.0h， 生成 cis-6-hydroxy-5-isobutyrylamino-3-(2-thienyl)-1-indanmethanol 、 trans-6-hydroxy-5-isobutyrylamino-3-(2-thienyl)-1-indanmethanol
  参考文献：
  名称：

  Design, syntheses, and structure–Activity relationships of indan derivatives as endothelin antagonists; new lead generation of non-peptidic antagonist from peptidic leads

  摘要：

  A new lead generation of non-peptidic ETA antagonists from two peptidic ETA-selective ones. BQ-123 and FR139317, was performed. Using computer assisted molecular modeling, a putative pharmacophore was constructed from the superposition of the reported three-dimensional structure of the cyclic peptide BQ-123 and a presumable beta -turn active conformation of the linear peptide FR139317 formed by an intramolecular hydrogen bond. According to this model, a new series of indan derivatives were designed and synthesized. Among these, 5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)-3-indancarboxylic acid (1b) showed a moderate ETA antagonistic activity (IC50=28 muM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00241-8
• 作为产物：
  描述：

  methyl 6-hydroxy-5-nitro-3-(2-thienyl)-1-indancarboxylate 在 盐酸 、 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 6-Amino-3-hydroxymethyl-1-thiophen-2-yl-indan-5-ol
  参考文献：
  名称：

  Design, syntheses, and structure–Activity relationships of indan derivatives as endothelin antagonists; new lead generation of non-peptidic antagonist from peptidic leads

  摘要：

  A new lead generation of non-peptidic ETA antagonists from two peptidic ETA-selective ones. BQ-123 and FR139317, was performed. Using computer assisted molecular modeling, a putative pharmacophore was constructed from the superposition of the reported three-dimensional structure of the cyclic peptide BQ-123 and a presumable beta -turn active conformation of the linear peptide FR139317 formed by an intramolecular hydrogen bond. According to this model, a new series of indan derivatives were designed and synthesized. Among these, 5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)-3-indancarboxylic acid (1b) showed a moderate ETA antagonistic activity (IC50=28 muM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00241-8