9H-嘌呤-6-胺,9-(3-苯基丙基)- | 17756-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 9H-嘌呤-6-胺,9-(3-苯基丙基)-
• 英文名称: 9-(3'-phenylpropyl)adenine
• 英文别名: 9-(3-Phenylpropyl)adenine；9-(3-phenylpropyl)purin-6-amine
• CAS: 17756-28-4
• 化学式: C₁₄H₁₅N₅
• 分子量: 253.307
• InChiKey: NACIDRWTSRNGSN-UHFFFAOYSA-N

物化性质

• 熔点：
  184-187 °C
• 沸点：
  491.2±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9H-嘌呤-6-胺,9-(3-苯基丙基)- 、 丙酮醛 以 水 为溶剂， 反应 168.0h， 以14%的产率得到(7R,8R,9S)-7,8-dihydroxy-7,9-dimethyl-3-(3-phenylpropyl)-8H-pyrimido[2,1-f]purine-9-carboxylic acid
  参考文献：
  名称：

  A new 9-alkyladenine-cyclic methylglyoxal diadduct activates wt- and F508del-cystic fibrosis transmembrane conductance regulator (CFTR) in vitro and in vivo

  摘要：

  Cystic fibrosis transmembrane conductance regulator (CFTR) is the main chloride channel present in the apical membrane of epithelial cells and the F508 deletion (F508del-CFTR) in the CF gene is the most common cystic fibrosis-causing mutation. In the search for a pharmacotherapy of cystic fibrosis caused by the F508del-CFTR, a bi-therapy could be developed associating a corrector of F508del-CFTR trafficking and an activator of the channel activity of CFTR. Here, we report on the synthesis of 9-alkyladenine derivatives analogues of our previously discovered activator of wt-CFTR and F508del-CFTR, GPact-11a, and the identification of a new activator of these channels, GPact-26a, through various flux assays on human airway epithelial CF and non-CF cell lines and in vivo measurement of rat salivary secretion. This study reveals that the possible modifications of the side chain introduced at the N9 position of the main pharmacophore are highly limited since only an allyl group can replace the propyl side chain present in GPact-11a to lead to a strong activation of wt-CFTR in CHO cells. Docking simulations of the synthesised compounds and of four described modulators performed using a 3D model of the wt-type CFTR protein suggest five possible binding sites located at the interface of the nucleotide binding domains NBD1/NBD2. However, the docking study did not allow the differentiation between active and non-active compounds.

  DOI：

  10.1016/j.ejmech.2014.06.028
• 作为产物：
  描述：

  1-溴-3-苯基丙烷 、 腺嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以57%的产率得到9H-嘌呤-6-胺,9-(3-苯基丙基)-
  参考文献：
  名称：

  [EN] COMPOUNDS FOR TREATING CYSTIC FIBROSIS
  [FR] COMPOSÉS POUR LE TRAITEMENT DE LA FIBROSE KYSTIQUE

  摘要：

  公开号：

  WO2016087665A3

文献信息

• Compounds for treating cystic fibrosis
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：US10414768B2

  公开（公告）日：2019-09-17

  The present invention relates to compounds of Formula (I) or pharmaceutically acceptable enantiomers, salts, solvates or prodrugs thereof. The invention further relates to the use of the compounds of Formula (I) for the treatment of cystic fibrosis. The invention also relates to a process for manufacturing compounds of Formula (I).

  本发明涉及式（I）化合物或其药学上可接受的对映体、盐、溶液剂或原药。本发明还涉及式（I）化合物用于治疗囊性纤维化的用途。本发明还涉及一种制造式（I）化合物的工艺。
• 9-(2-Aryloxyethyl) Derivatives of Adenine - a New Class of Non-nucleosidic Antiviral Agents
  作者：V. I. Petrov、A. A. Ozerov、M. S. Novikov、C. Pannecouque、J. Balzarini、E. De Clercq

  DOI：10.1023/b:cohc.0000008270.32235.2b

  日期：2003.9
• UTILISATION MEDICALE DE COMPOSES ZWITTERIONIQUES COMME MODULATEURS DES CANAUX CFTR
  申请人：UNIVERSITE JOSEPH FOURIER

  公开号：EP1678175B1

  公开（公告）日：2008-02-13
• COMPOUNDS FOR TREATING CYSTIC FIBROSIS
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP3226861A2

  公开（公告）日：2017-10-11
• US7772198B2
  申请人：——

  公开号：US7772198B2

  公开（公告）日：2010-08-10