N⁶-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde hydrate | 43077-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N⁶-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde hydrate
• 英文别名: 6-N-benzoyl-9-(2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,5-furanosyl)adeninehydrate；N-[9-[(3aR,4R,6S,6aS)-6-(dihydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-yl]benzamide
• CAS: 43077-04-9
• 化学式: C₂₀H₂₁N₅O₆
• 分子量: 427.417
• InChiKey: GNYAWJBHHADTBR-MOROJQBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde hydrate 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 5.67h， 生成 5'-desoxy-5'-butyladenosine
  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
• 作为产物：
  描述：

  N⁶-benzoyl-5'-deoxy-2',3'-O-isopropylidiene-5',5'-(N,N'-diphenylethylenediamino)adenosine 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以67%的产率得到N⁶-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde hydrate
  参考文献：
  名称：

  Hemisynthesis of deuteriated adenosylhopane and conversion into bacteriohopanetetrol by a cell-free system from Methylobacterium organophilum

  摘要：

  (²H₂)腺苷基合成藿烷是通过交叉重合反应后，随后对产生的烯烃进行N₂²H₂还原反应而合成的。

  DOI：

  10.1039/c4ob02560a

文献信息

• [EN] SUBSTITUTED NUCLEOSIDE ANALOGUES FOR USE AS PRMT5 INHIBITORS<br/>[FR] ANALOGUES DE NUCLÉOSIDES SUBSTITUÉS DESTINÉS À ÊTRE UTILISÉS EN TANT QU'INHIBITEURS DE PRMT5
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2017153186A1

  公开（公告）日：2017-09-14

  The present invention relates novel substituted nucleoside analogues of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as PRMT5 inhibitors. The invention further relates to pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及式(I)的新型取代核苷类似物，其中变量具有如权利要求中所定义的含义。根据本发明的化合物作为PRMT5抑制剂是有用的。本发明进一步涉及包含所述化合物作为活性成分的药物组合物，以及将所述化合物用作药物的应用。
• Stereoselective adenylate deaminase (5′-adenylic acid deaminase, AMPDA)-catalyzed deamination of 5′-alkyl substituted adenosines: a comparison with the action of adenosine deaminase (ADA)
  作者：Pierangela Ciuffreda、Angela Loseto、Enzo Santaniello

  DOI：10.1016/j.tetasy.2003.11.007

  日期：2004.1

  The enzymes adenylate deaminase (AMPDA) and adenosine deaminase (ADA) are able to catalyze the stereoselective hydrolytic deamination of (5′R,S)-methyl-2′,3′-isopropylidene adenosine, but the 5′-butyl analog is a substrate only for AMPDA, which stereospecifically converts the (5′S)-isomer to the corresponding inosine derivative.

  酶腺苷酸脱氨酶（AMPDA）和腺苷脱氨酶（ADA）是能够催化（5的立体选择性水解的脱氨基' - [R ，小号） -甲基- 2 ' ，3 '异亚丙基腺苷，但5 ' -丁基类似物是基材仅AMPDA，其立体专一性转换（5 '小号） -异构体为相应的肌苷衍生物。
• NOVEL SUBSTITUTED NUCLEOSIDE ANALOGUES FOR USE AS PRMT5 INHIBITORS
  申请人：Janssen Pharmaceutica NV

  公开号：US20200289539A1

  公开（公告）日：2020-09-17

  The present invention relates novel substituted nucleoside analogues of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as PRMT5 inhibitors. The invention further relates to pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.