2-(5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)indan-1-ylmethylene)-1,3-dithiane | 339309-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)indan-1-ylmethylene)-1,3-dithiane
• CAS: 339309-65-8
• 化学式: C₃₃H₃₃NO₂S₃
• 分子量: 571.829
• InChiKey: VQSXXIXYBZBCBP-UHFFFAOYSA-N

物化性质

• 沸点：
  766.6±60.0 °C(predicted)
• 密度：
  1.311±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.41
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-(5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)indan-1-ylmethylene)-1,3-dithiane 在 mercury dichloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 trans-methyl 5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)-1-indanacetate 、 cis-methyl 5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)-1-indanacetate
  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：

  5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)-1-indanmethanol 在 sodium hydride 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 2-(5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)indan-1-ylmethylene)-1,3-dithiane
  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