5'-desoxy-5'-benzyladenosine | 595608-06-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-desoxy-5'-benzyladenosine
• 英文别名: (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(2-phenylethyl)oxolane-3,4-diol
• CAS: 595608-06-3
• 化学式: C₁₇H₁₉N₅O₃
• 分子量: 341.37
• InChiKey: YUNLULSMDPCDNP-LSCFUAHRSA-N

物化性质

• 沸点：
  654.7±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-desoxy-5'-benzyladenosine 在 potassium phosphate buffer 、 rh 5'-deoxy-5'-methylthioadenosine phosphorylase 作用下， 生成 、 腺嘌呤
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel human 5′-deoxy-5′-methylthioadenosine phosphorylase (MTAP) substrates

  摘要：

  The structure-based design, chemical synthesis, and biological evaluation of novel MTAP substrates are described. These compounds incorporate various C5'-moieties and are shown to have different k(cat)/K values compared with the natural MTAP substrate (MTA). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.107
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 吡啶 、 二氯乙酸 、 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 6.17h， 生成 5'-desoxy-5'-benzyladenosine
  参考文献：
  名称：

  Analogues of the Natural Product Sinefungin as Inhibitors of EHMT1 and EHMT2

  摘要：

  A series of analogues of the natural product sinefungin lacking the amino acid moiety was synthesized and probed for their ability to inhibit EHMT1 and EHMT2. This study led to inhibitors 3b and 4d of methyltransferase activity of EHMT1 and EHMT2 and it demonstrates that such analogues constitute an interesting scaffold to develop selective methyltransferase inhibitors. Surprisingly, the inhibition was not competitive toward Ado Met.

  DOI：

  10.1021/ml4002503

文献信息

• EPIGENETIC REGULATORS OF FRATAXIN
  申请人：Rana Therapeutics Inc.

  公开号：EP3033423A1

  公开（公告）日：2016-06-22
• [EN] EPIGENETIC REGULATORS OF FRATAXIN<br/>[FR] RÉGULATEURS ÉPIGÉNÉTIQUES DE LA FRATAXINE
  申请人：RANA THERAPEUTICS INC

  公开号：WO2015023938A1

  公开（公告）日：2015-02-19

  Provided herein are methods for increasing Frataxin (FXN) expression that involve targeting or expressing regulatory factors that modulate the epigenetic state of FXN genes. Also provided herein are methods for increasing FXN expression using inhibitors of a negative epigenetic regulator of FXN. Compositions and methods for treating Friedrich' s ataxia are also provided.
• Analogues of the Natural Product Sinefungin as Inhibitors of EHMT1 and EHMT2
  作者：Kanchan Devkota、Brian Lohse、Qing Liu、Ming-Wei Wang、Dan Stærk、Jens Berthelsen、Rasmus Prætorius Clausen

  DOI：10.1021/ml4002503

  日期：2014.4.10

  A series of analogues of the natural product sinefungin lacking the amino acid moiety was synthesized and probed for their ability to inhibit EHMT1 and EHMT2. This study led to inhibitors 3b and 4d of methyltransferase activity of EHMT1 and EHMT2 and it demonstrates that such analogues constitute an interesting scaffold to develop selective methyltransferase inhibitors. Surprisingly, the inhibition was not competitive toward Ado Met.
• Design, synthesis, and biological evaluation of novel human 5′-deoxy-5′-methylthioadenosine phosphorylase (MTAP) substrates
  作者：Pei-Pei Kung、Luke R. Zehnder、Jerry J. Meng、Stanley W. Kupchinsky、Donald J. Skalitzky、M. Catherine Johnson、Karen A. Maegley、Anne Ekker、Leslie A. Kuhn、Peter W. Rose、Laura A. Bloom

  DOI：10.1016/j.bmcl.2005.03.107

  日期：2005.6

  The structure-based design, chemical synthesis, and biological evaluation of novel MTAP substrates are described. These compounds incorporate various C5'-moieties and are shown to have different k(cat)/K values compared with the natural MTAP substrate (MTA). (c) 2005 Elsevier Ltd. All rights reserved.