9-N-<(2'-deoxy-β-D-ribo-pentofuranosyl)methyl>adenine | 170983-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-N-<(2'-deoxy-β-D-ribo-pentofuranosyl)methyl>adenine
• 英文别名: 2'-deoxy-1'-homoadenosine；2,5-Anhydro-1,3-dideoxy-1-(adenin-9-yl)-D-allitol；(2R,3S,5R)-5-[(6-aminopurin-9-yl)methyl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 170983-95-6
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: CZFKVDJTVMYHLS-GJMOJQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  9-N-<(2'-deoxy-β-D-ribo-pentofuranosyl)methyl>adenine 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 生成
  参考文献：
  名称：

  Homo-N-oligonucleotides (N1/N9−C1‘ Methylene Bridge Oligonucleotides):  Nucleic Acids with Left-Handed Helicity

  摘要：

  Oligonucleotides containing a methylene bridge between N1 or N9 of the heterocyclic base and C1' of the pentofuranosyl ring (homo-N-oligonucleotides) were synthesized. Melting curves revealed that such homo-type oligomers could cross-pair with complementary homo-type or natural oligomers. Circular-dichroic studies provide evidence that the homo-type dinners have a left-handed stacked conformation and further suggest that single-stranded and double-stranded homo-type oligomers adopt a left-handed conformation, while duplexes with natural oligomers or nucleic acids form RNA-like right-handed helices. NMR spectroscopy (NOESY) provides supporting evidence for a left-handed stacked conformation of the homo-type dimer, while atomic force microscopy indicates a left-handed helical conformation of homotype dsDNA. Homo-type dinners and oligomers showed high resistance to digestion by snake-venom and calf-spleen phosphodiesterases and nuclease S1.

  DOI：

  10.1021/ja049865t
• 作为产物：
  描述：

  1-C-(methanesulfonyloxy)methyl-3,5-dibenzyl-2-deoxy-β-D-ribose 在 palladium 10% on activated carbon 、 氢气 、 双氧水 、 甲基三氧化铼(VII) 、 sodium hydride 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 9-N-<(2'-deoxy-β-D-ribo-pentofuranosyl)methyl>adenine
  参考文献：
  名称：

  甲基三氧杂ox（MTO）/ H2O2的氧官能化反应合成具有抗流感活性的2'-脱氧-1'-高纯N-核苷

  摘要：

  本文介绍了一种新的途径，可以通过甲基三氧nucleo（MTO）或负载型MTO催化剂，以H 2 O 2为主要氧化剂，合成1'-homo- N-核苷衍生物。在这些选择条件下，无论所用的底物类型为嘌呤或嘧啶衍生物，杂环的氧官能化和N杂原子氧化都是有效的过程。此外，1'-同型N-硫代核苷的氧化表明杂环发生了位点特异性氧化亲核取代。MTO / H 2 O 2该系统通常显示出在均相和非均相条件下均具有高反应活性，为最终产物提供了高底物转化率和中等至高收率的最终产物。许多新颖的1'-homo- N-核苷类似物对A型流感病毒都具有活性，而没有任何细胞毒性作用，并以受保护和不受保护的形式保留其活性。

  DOI：

  10.1002/chem.201201285

文献信息

• Synthesis of homo-N-nucleosides, a series of C1' branched-chain nucleosides
  作者：Nafizal Hossain、Norbert Blaton、Oswald Peeters、Jef Rozenski、Piet A. Herdewijn

  DOI：10.1016/0040-4020(96)00192-5

  日期：1996.4

  Homo-N-desoxynucleosides were synthesized starting from 2-deoxy-d-ribose using a one step epoxidation-ring closure appraoch. The configuration of the nucleosides were proven using NMR and X-ray analysis.

  使用一步环氧化环封闭方法，从2-脱氧-d-核糖开始合成人-N-脱氧核苷。使用NMR和X射线分析证明了核苷的构型。
• Antiviral c-nucleoside derivatives
  申请人：Nippon Shinyaku Co. Ltd.

  公开号：US05703224A1

  公开（公告）日：1997-12-30

  The present invention is composed of a nucleoside derivative of the following general formula \x9bI!: ##STR1## (wherein B represents adenin-9-ylmethyl, guanin-9-ylmethyl, hypoxanthin-9-ylmethyl, thymin-1-ylmethyl, uracil-1-ylmethyl, or cytosin-1-ylmethyl; X and Y may be the same or different and each represents hydrogen or hydroxy, exclusive of the case in which X is hydrogen and Y is hydroxy). The compound of the present invention is useful as an antiviral agent or an antimalignant-tumoral agent.

  本发明由以下一般式的核苷酸衍生物组成：\x9bI!: ##STR1##（其中B代表腺嘌呤-9-基甲基，鸟嘌呤-9-基甲基，次黄嘌呤-9-基甲基，胸腺嘧啶-1-基甲基，尿嘧啶-1-基甲基或胞嘧啶-1-基甲基；X和Y可以相同也可以不同，每个代表氢或羟基，不包括X为氢，Y为羟基的情况）。本发明的化合物可用作抗病毒剂或抗恶性肿瘤剂。
• NUCLEOSIDE DERIVATIVE
  申请人：NIPPON SHINYAKU COMPANY, LIMITED

  公开号：EP0733630A1

  公开（公告）日：1996-09-25

  The present invention is composed of a nucleoside derivative of the following general formula [I]: (wherein B represents adenin-9-ylmethyl, guanin-9-ylmethyl, hypoxanthin-9-ylmethyl, thymin-1-ylmethyl, uracil-1-ylmethyl, or cytosin-1-ylmethyl; X and Y may be the same or different and. each represents hydrogen or hydroxy, exclusive of the case in which X is hydrogen and Y is hydroxy). The compound of the present invention is useful as an antiviral agent or an antimalignant-tumoral agent.

  本发明由以下通式[I]的核苷衍生物组成： (其中B代表腺嘌呤-9-基甲基、鸟嘌呤-9-基甲基、次黄嘌呤-9-基甲基、百里酚-1-基甲基、尿嘧啶-1-基甲基或胞嘧啶-1-基甲基；X和Y可以相同或不同，各自代表氢或羟基，X为氢而Y为羟基的情况除外）。 本发明的化合物可用作抗病毒剂或抗恶性肿瘤剂。
• US5703224A
  申请人：——

  公开号：US5703224A

  公开（公告）日：1997-12-30
• Homo-<i>N</i>-oligonucleotides (N1/N9−C1‘ Methylene Bridge Oligonucleotides):  Nucleic Acids with Left-Handed Helicity
  作者：Kouichi Ishiyama、Gerald E. Smyth、Toshihiro Ueda、Yutaka Masutomi、Tadaaki Ohgi、Junichi Yano

  DOI：10.1021/ja049865t

  日期：2004.6.23

  Oligonucleotides containing a methylene bridge between N1 or N9 of the heterocyclic base and C1' of the pentofuranosyl ring (homo-N-oligonucleotides) were synthesized. Melting curves revealed that such homo-type oligomers could cross-pair with complementary homo-type or natural oligomers. Circular-dichroic studies provide evidence that the homo-type dinners have a left-handed stacked conformation and further suggest that single-stranded and double-stranded homo-type oligomers adopt a left-handed conformation, while duplexes with natural oligomers or nucleic acids form RNA-like right-handed helices. NMR spectroscopy (NOESY) provides supporting evidence for a left-handed stacked conformation of the homo-type dimer, while atomic force microscopy indicates a left-handed helical conformation of homotype dsDNA. Homo-type dinners and oligomers showed high resistance to digestion by snake-venom and calf-spleen phosphodiesterases and nuclease S1.