(2R,3R,4S,5S)-4-amino-5-(hydroxymethyl)-2-[6-(naphthalen-1-ylmethylamino)purin-9-yl]oxolan-3-ol | 676558-83-1

• 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: (2R,3R,4S,5S)-4-amino-5-(hydroxymethyl)-2-[6-(naphthalen-1-ylmethylamino)purin-9-yl]oxolan-3-ol
• CAS: 676558-83-1
• 化学式: C₂₁H₂₂N₆O₃
• 分子量: 406.444
• InChiKey: RAGSPZOBLXGEKS-BZSOYRFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(2-噻吩基)丁酸 、 (2R,3R,4S,5S)-4-amino-5-(hydroxymethyl)-2-[6-(naphthalen-1-ylmethylamino)purin-9-yl]oxolan-3-ol 以96%的产率得到3'-deoxy-N⁶-(1-naphthylmethyl)-3'-[4-(2-thienyl)butanamido]adenosine
  参考文献：
  名称：

  Antimalarial activity of N6-substituted adenosine derivatives. Part 3

  摘要：

  A series of novel 3'-amido-3'-deoxy-N-6-(l-naphthylmethyl)adenosines was synthesized applying a polymer-assisted solution phase (PASP) protocol and was tested for anti-malarial activity versus the Dd2 strain of Plasm odium falciparum. Further, this series and 62 adenosine derivatives were analyzed regarding 1-deoxy-D-xylulose 5-phospate (DOXP) reductoisomerase inhibition. Biological evaluations revealed that the investigated 3,N-6-disubstituted adenosine derivatives displayed moderate but significant activity against the P. falciparum parasite in the low-micromolar range. On the molecular level, DOXP reductoisomerase utilizing an adenosyl-containing substrate was identified as a promising metabolic target for ligands of adenosine binding motifs. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.008
• 作为产物：
  描述：

  1-萘甲基胺 在 indium 、 氯化铵 、 N,N-二异丙基乙胺 作用下， 以 丙醇 、 乙醇 为溶剂， 反应 8.0h， 生成 (2R,3R,4S,5S)-4-amino-5-(hydroxymethyl)-2-[6-(naphthalen-1-ylmethylamino)purin-9-yl]oxolan-3-ol
  参考文献：
  名称：

  Antimalarial activity of N6-substituted adenosine derivatives. Part 3

  摘要：

  A series of novel 3'-amido-3'-deoxy-N-6-(l-naphthylmethyl)adenosines was synthesized applying a polymer-assisted solution phase (PASP) protocol and was tested for anti-malarial activity versus the Dd2 strain of Plasm odium falciparum. Further, this series and 62 adenosine derivatives were analyzed regarding 1-deoxy-D-xylulose 5-phospate (DOXP) reductoisomerase inhibition. Biological evaluations revealed that the investigated 3,N-6-disubstituted adenosine derivatives displayed moderate but significant activity against the P. falciparum parasite in the low-micromolar range. On the molecular level, DOXP reductoisomerase utilizing an adenosyl-containing substrate was identified as a promising metabolic target for ligands of adenosine binding motifs. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.008

文献信息

• METALLO-OXIDOREDUCTASE INHIBITORS USING METAL BINDING MOIETIES IN COMBINATION WITH TARGETING MOIETIES
  申请人：Viamet Pharmaceuticals, Inc.

  公开号：EP2086546A2

  公开（公告）日：2009-08-12
• US8680270B2
  申请人：——

  公开号：US8680270B2

  公开（公告）日：2014-03-25
• [EN] METALLO-OXIDOREDUCTASE INHIBITORS USING METAL BINDING MOIETIES IN COMBINATION WITH TARGETING MOIETIES<br/>[FR] INHIBITEURS DE LA MÉTALLO-OXYDORÉDUCTASE FAISANT APPEL À DES FRACTIONS SE LIANT AUX MÉTAUX EN COMBINAISON AVEC DES FRACTIONS DE CIBLAGE
  申请人：VIAMET PHARMACEUTICALS INC

  公开号：WO2008064311A2

  公开（公告）日：2008-05-29

  [EN] The presently disclosed subject matter is directed to metallo-oxidoreductase inhibitors having metal binding moities linked to a targeting moiety through a linking group or a direct bond, methods for screening for metallo-oxidoreductase inhibitors, and methods of treating an oxidoreductase related disorder by administering a metallo- oxidoreductase inhibitor to a subject in need of treatment thereof.
  [FR] L'invention concerne des inhibiteurs de métallo-oxydoréductase faisant appel à des fractions se liant aux métaux liées à une fraction de ciblage par un groupe de liaisons ou par liaison directe, des procédés de criblage pour des inhibiteurs de métallo-oxydoréductase, et des procédés de traitement d'un trouble lié à l'oxydoréductase par l'administration d'un inhibiteur de métallo-oxydoréductase à un sujet en requérant le traitement.