6-(1-Benzyl-1-methylethylamino)-9-(β-D-ribofuranosyl)purine | 97826-35-2

• 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: 6-(1-Benzyl-1-methylethylamino)-9-(β-D-ribofuranosyl)purine
• 英文别名: n6-(2-Methyl-1-phenyl-2-propyl)adenosine；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[(2-methyl-1-phenylpropan-2-yl)amino]purin-9-yl]oxolane-3,4-diol
• CAS: 97826-35-2
• 化学式: C₂₀H₂₅N₅O₄
• 分子量: 399.45
• InChiKey: FEKCMDDMLYKDNY-NVQRDWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2’,3’,5’-三乙酰肌苷 在 氯化亚砜 、 sodium 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 6-(1-Benzyl-1-methylethylamino)-9-(β-D-ribofuranosyl)purine
  参考文献：
  名称：

  狗冠状动脉腺苷受体：N6-烷基亚区域的结构。

  摘要：

  N6- [1-苯基-2（R）-丙基]腺苷（​​1）的中等有效和立体选择性冠状血管活性是本研究的基础，该研究通过以下结构绘制了冠状动脉腺苷受体的N6区域：开胸犬1的81个类似物的冠状动脉血管活性关系。立体选择性是具有与N6相邻的手性中心的N6-取代的腺苷的一般性质。1与它的S非对映异构体的活性比为10，这是与R非对映异构体的丙基C-3基团的受体发生正向相互作用的结果，以及该S非对映异构体基团施加的空间位阻。用乙基，苯基，苯乙基或萘基取代1的苄基部分会降低R非对映异构体的效力，并因此降低R / S比。1的丙基C-1与一个足以容纳三个亚甲基残基的受体区域相互作用，而丙基C-3残基与一个足以容纳两个亚甲基残基的独立区域相互作用。与1的丙基C-1相互作用的受体子区域比与丙基C-3相互作用的子区域更能容忍本体和极性取代基。关于N6对活性的可能贡献（例如通过氢键）的证据尚不明确。这些结果支持了N6-烷基

  DOI：

  10.1021/jm00149a016

文献信息

• Anti-HCV nucleoside derivatives
  申请人：——

  公开号：US20030008841A1

  公开（公告）日：2003-01-09

  The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。
• NUCLEOSIDE DERIVATIVES FOR THE TREATMENT OF HEPATITIS C
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1315736A2

  公开（公告）日：2003-06-04
• [EN] NUCLEOSIDE DERIVATIVES<br/>[FR] DERIVES DE NUCLEOSIDES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002018404A2

  公开（公告）日：2002-03-07

  Use of compounds of formula (I), wherein R1 is hydrogen, hydroxy, alkyl, hydroxyalkyl, alkoxy, halogen, cyano, isocyano or azido; R2 is hydrogen, hydroxy, alkoxy, chlorine, bromine or iodine; R3 is hydrogen; or R?2 and R3¿ together represent =CH¿2?; or R?2 and R3¿ represent fluorine; X is O, s or CH¿2?; a, b, c, d denoting asymmetric carbon atoms each of which is substituted with 4 different substituents; and B signifies a purine base B1 which is connected through the 9-nitrogen of formula (B1), wherein R?4¿ is hydrogen, hydroxyl, alkyl, alkoxy, alkylthio, aryloxy, arylthio, heterocyclyl, NR7R8, halogen or SH; R5 is hydrogen, hydroxy, alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, heterocyclyl, heterocyclylamino, halogen, NR?7R8, NHOR9, NHNR7R8¿ or SH; R6 is hydrogen, hydroxy, alkyl, alkoxy, alkylthio, aryloxy, arylthio, heterocyclyl, NR7R8, halogen, SH or cyano; R?7 and R8¿ are independently of each other hydrogen, alkyl, aryl, hydroxyalkyl, alkenylalkyl, alkynylalkyl, cycloalkyl or acyl; R9 is hydrogen, alkyl or aryl; or B signifies an oxidised purine base B2 which is connected through the 9-nitrogen of formula (B2), wherein R?4, R5 and R6¿ are as defined above; or B signifies a purine base B3 which is connected through the 9-nitrogen of formula (B3), wherein R?4 and R6¿ are as defined above; R10 is hydrogen, alkyl or aryl; Y is O, S or NR11; R11 is hydrogen, hydroxy, alkyl, OR9, heterocyclyl or NR?7R8; R7, R8 and R9¿ are as defined above; or B signifies a pyrimidine base B4 which is connected through the 1-nitrogen of formula (B4), wherein Z is O or S; R12 is hydrogen, hydroxy, alkyl, alkoxy, haloalkyl, alkylthio, aryl, aryloxy, arylthio, heterocyclyl, heterocyclylamino, halogen, NR?7R8, NHOR9, NHNR7R8¿ or SH; R13 is hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, haloalkyl, cycloalkyl or halogen; R?7, R8 and R9¿ are as defined above; or B signifies a pyrimidine base B5 which is connected through the 1-nitrogen of formula (B5), wherein Y, Z, R10 are as defined above for the treatment of diseases mediated by the Hepatitis C Virus (HIV) or for the preparation of a medicament for such treatment. The invention is concerned with novel and known purine and pyrimidine nucleoside derivatives, their use as inhibitors of subgenomic Hepatitis C Virus (HCV) RNA replication and pharmaceutical compositions of such compounds.
• Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion
  作者：Shozo Kusachi、Robert D. Thompson、William J. Bugni、Nobuyuki Yamada、Ray A. Olsson

  DOI：10.1021/jm00149a016

  日期：1985.11

  The moderately potent and stereoselective coronary vasoactivity of N6-[1-phenyl-2(R)-propyl]adenosine (1) is the basis for the present study that maps the N6 region of the coronary artery adenosine receptor by means of the structure-coronary vasoactivity relationships of 81 analogues of 1 in the open-thorax dog. Stereoselectivity is a general property of N6-substituted adenosines that have a chiral

  N6- [1-苯基-2（R）-丙基]腺苷（​​1）的中等有效和立体选择性冠状血管活性是本研究的基础，该研究通过以下结构绘制了冠状动脉腺苷受体的N6区域：开胸犬1的81个类似物的冠状动脉血管活性关系。立体选择性是具有与N6相邻的手性中心的N6-取代的腺苷的一般性质。1与它的S非对映异构体的活性比为10，这是与R非对映异构体的丙基C-3基团的受体发生正向相互作用的结果，以及该S非对映异构体基团施加的空间位阻。用乙基，苯基，苯乙基或萘基取代1的苄基部分会降低R非对映异构体的效力，并因此降低R / S比。1的丙基C-1与一个足以容纳三个亚甲基残基的受体区域相互作用，而丙基C-3残基与一个足以容纳两个亚甲基残基的独立区域相互作用。与1的丙基C-1相互作用的受体子区域比与丙基C-3相互作用的子区域更能容忍本体和极性取代基。关于N6对活性的可能贡献（例如通过氢键）的证据尚不明确。这些结果支持了N6-烷基