5,6,7-trimethoxy-3-trifluoroacetylaminoindan-1-one | 138621-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5,6,7-trimethoxy-3-trifluoroacetylaminoindan-1-one
• 英文别名: 2,3-Dihydro-3-(trifluoroacetylamino)-5,6,7-trimethoxy-1H-indene-1-one；2,2,2-trifluoro-N-(4,5,6-trimethoxy-3-oxo-1,2-dihydroinden-1-yl)acetamide
• CAS: 138621-68-8
• 化学式: C₁₄H₁₄F₃NO₅
• 分子量: 333.264
• InChiKey: RVUNNOTXEUOOJP-UHFFFAOYSA-N

物化性质

• 沸点：
  468.0±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,6,7-trimethoxy-3-trifluoroacetylaminoindan-1-one 在 chromium(VI) oxide 、 盐酸 、 硫酸 、 水 、 sodium nitrite 作用下， 以 盐酸 、 丙酮 为溶剂， 反应 2.5h， 生成 4,5,6-trimethoxyindane-1,3-dione
  参考文献：
  名称：

  Dallemagne, P.; Pilo, J. C.; Rault, S., Bulletin de la Societe Chimique de France, 1993, vol. 130, # 1, p. 121 - 124

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 ammonium acetate 、 三氟乙酸 作用下， 反应 3.0h， 生成 5,6,7-trimethoxy-3-trifluoroacetylaminoindan-1-one
  参考文献：
  名称：

  一锅环化的烷氧基-3-氨基茚满-1-酮。

  摘要：

  3-Amino-3-alkoxyphenylpropionic acids, prepared from alkoxybenzaldehydes, are cyclized in one step into 3-aminoindan-1-ones using trifluoroacetic acid and trifluoroacetic anhydride.

  DOI：

  10.1016/0040-4039(91)80160-8

文献信息

• Effective cerebral antihypoxic activity of new aminocyclopentanones
  作者：MA Quermonne、P Dallemagne、J Louchahi-Raoul、JC Pilo、S Rault、M Robba

  DOI：10.1016/0223-5234(92)90029-z

  日期：1992.12

  Effective antihypoxic activity of new aminocyclopentanones which was higher than that of the reference compounds has been demonstrated by the SCR hypoxia test.
• Evidence for new non-steroidal human aromatase inhibitors and comparison with equine aromatase inhibition for an understanding of the mammalian active site
  作者：Pierrick Auvray、Safa Moslemi、Pascal Sourdaine、Sébastien Galopin、Gilles-Eric Séralini、Cécile Enguehard、Patrick Dallemagne、Ronan Bureau、Pascal Sonnet、Sylvain Rault

  DOI：10.1016/s0223-5234(98)80046-9

  日期：1998.6

  We developed a new comparative model in order to better understand the structure-function relationships of the active site in human aromatase. Thus, we undertook the comparative inhibition of human and equine aromatases with new compounds. In fact, equine aromatase represents the only easy and available mammalian membrane-bound enzyme model, besides the human one, which is biochemically purified, well characterized and cloned. During the course of our work concerning the synthesis and screening of new drugs on human and equine aromatases, we identified two new indane derivatives which inhibited the human enzyme (IC50 = 3.5 mu M and 5.9 mu M) strongly and selectively while they were much less active on the equine one (IC50 > 10 mu M). The hitherto known aromatase inhibitors, such as 4-hydroxyandrostenedione (4-OHA) and some other indane-related derivatives, are equally efficient on both human and equine enzymes. In this work, using a theoretical 3D model of aromatase, we have explained the human selectivity of the new described compounds as due to the specific differences between the primary structure of both active sites in human and equine enzymes. These results could allow synthesis of a new family of compounds that are much more potent and selective aromatase inhibitors. (C) Elsevier, Paris.