8-(phenylamino)adenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-(phenylamino)adenosine
• 英文别名: N-(adenosin-8-yl)aniline；(2R,3R,4S,5R)-2-(6-amino-8-anilinopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₁₆H₁₈N₆O₄
• 分子量: 358.357
• InChiKey: ZLPPPFWZUAKOBV-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  8-溴膘苷 在 咪唑 、 氟化铵 、 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 97.0h， 生成 8-(phenylamino)adenosine
  参考文献：
  名称：

  Identification of 8-Aminoadenosine Derivatives as a New Class of Human Concentrative Nucleoside Transporter 2 Inhibitors

  摘要：

  Purine-rich foods have long been suspected as a major cause of hyperuricemia. We hypothesized that inhibition of human concentrative nucleoside transporter 2 (hCNT2) would suppress increases in serum urate levels derived from dietary purines. To test this hypothesis, the development of potent hCNT2 inhibitors was required. By modifying adenosine, an hCNT2 substrate, we successfully identified 8-aminoadenosine derivatives as a new class of hCNT2 inhibitors. Compound 12 moderately inhibited hCNT2 (IC50 = 52 +/- 3.8 mu M), and subsequent structure-activity relationship studies led to the discovery of compound 48 (IC50 = 0.64 +/- 0.19 mu M). Here we describe significant findings about structural requirements of 8-aminoadenosine derivatives for exhibiting potent hCNT2 inhibitory activity.

  DOI：

  10.1021/ml500343r

文献信息

• SYNTHESIS AND CHARACTERIZATION OF ADENOSINE ADDUCTS OF ARYLAMINES
  作者：N. V. Anil Kumar、K. Mantelingu、K. S. Rangappa

  DOI：10.1081/ncn-120014818

  日期：——

  Aromatic amines and nitroarenes are very important industrial intermediates. Several scientists ([1,2]) have extensively studied the covalent binding of a number of aromatic amines to DNA and identified various products by studying in vivo and in vitro reactions of esters of aryl hydroxylamine.([3]) Aromatic amines can be metabolised to highly reactive N-hydroxy aromatic amines. These are highly reactive intermediates which are responsible for the genotoxic effects of this class of compounds. DNA adducts of arylamines have been found in several organs of exposed experimental animals. With the advancement in analytical technique, scientists have quantified the DNA adducts of arylamines in human tissue. Therefore, the reference standards of DNA adducts have been synthesized. The deoxyguanosine adducts of arylamines by synthesis are known([4-7]) but not the adenosine adducts. Hence, this study of the reaction of arylamines with adenosine is undertaken.
• Carboxyamidation of Purine Nucleosides: New Secondary 8-Carboxamidopurine Nucleosides
  作者：Chi Tu、Charlene Keane、Bruce Eaton

  DOI：10.1080/07328319708001344

  日期：1997.3

  Palladium catalyzed carboxyamidation at the 8-position of 8-bromoadenosine and 8-bromoguanosine nucleosides is a versatile reaction, which allows primary, secondary, heterocyclic, aromatic amine and amino acids to be incorporated into purine nucleosides.
• Screening method
  申请人：——

  公开号：US20040013609A1

  公开（公告）日：2004-01-22

  The invention relates to a method for identification of substances which are applicable for treatment or prevention of an insufficient longitudinal growth of the eye (hypermetropia) or for treatment or prevention of an excessive longitudinal growth of the eye (myopia); substances identified by the method for treating or preventing conditions related to the longitudinal growth of the eye; substances and mixtures of substances for the preparation of a pharmaceutical composition for the treatment or prevention of abnormal growth of the axial length of the eye. The identification involves measuring the effect of the substances on the retinal pigment epithelium of the eye, e.g. by detecting the metabolic effect of the substance on the retinal epithelium, the effect on the standing potential or the effect on the proteoglycanes of the scleral tissue of the eye, by way of EOG examination, by way on the size of the so-called c-wave in ERG-recordings, or by the state of the Ca 2+ -channels or on the [ 3 H]-ryanodine receptors of the retinal pigment epithelium.
• US6710051B1
  申请人：——

  公开号：US6710051B1

  公开（公告）日：2004-03-23
• [EN] SCREENING METHOD<br/>[FR] PROCEDE DE SELECTION
  申请人：KLAUS TRIER APS

  公开号：WO1998030900A2

  公开（公告）日：1998-07-16

  (EN) The invention relates to a method for identification of substances which are applicable for treatment or prevention of an insufficient longitudinal growth of the eye (hypermetropia) or for treatment or prevention of an excessive longitudinal growth of the eye (myopia); substances identified by the method for treating or preventing conditions related to the longitudinal growth of the eye; substances and mixtures of substances for the preparation of a pharmaceutical composition for the treatment or prevention of abnormal growth of the axial length of the eye. The identification involves measuring the effect of the substances on the retinal pigment epithelium of the eye, e.g. by detecting the metabolic effect of the substance on the retinal epithelium, the effect on the standing potential or the effect on the proteoglycanes of the scleral tissue of the eye, by way of EOG examination, by way on the size of the so-called c-wave in ERG-recordings, or by the state of the Ca2+-channels or on the [3H]-ryanodine receptors of the retinal pigment epithelium.(FR) Procédé pour identifier des substances pouvant être utilisées pour le traitement ou la prévention d'une croissance longitudinale insuffisante de l'oeil (hypermétropie) ou pour le traitement ou la prévention d'une croissance longitudinale excessive de l'oeil (myopie). L'invention porte également sur des substances identifiées par ce procédé, pour le traitement et la prévention de troubles liés à la croissance longitudinale de l'oeil, et sur des substances et mélanges de substances servant à préparer une composition pharmaceutique pour le traitement ou la prévention d'une croissance anormale de la longueur axiale de l'oeil. L'identification consiste à mesurer l'effet des substances sur l'épithélium pigmentaire de la rétine, p. ex. en détectant l'effet métabolique de la substance sur cet épithélium, l'effet sur le potentiel stationnaire ou l'effet sur les protéoglycanes du tissu scléral de l'oeil, au moyen d'une électro-occulographie, en mesurant l'amplitude de 'l'onde c' dans les électrorétinogrammes ou en se référant à l'état des canaux de Ca2+ ou des récepteurs de [3H]-ryanodine de l'épithélium pigmentaire de la rétine.