3'-O-allyl Adenosine | 400820-99-7

• 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: 3'-O-allyl Adenosine
• 英文别名: 3'-O-Allyladenosine；(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-4-prop-2-enoxyoxolan-3-ol
• CAS: 400820-99-7
• 化学式: C₁₃H₁₇N₅O₄
• 分子量: 307.309
• InChiKey: KURUYHOEDIRMCE-QYVSTXNMSA-N

物化性质

• 沸点：
  632.8±65.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-O-allyl Adenosine 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  Design and synthesis of 3′,5′-ansa-adenosines as potential Hsp90 inhibitors

  摘要：

  3',5'-Ansa-adenosine derivatives, rationally designed as an Hsp90 inhibitor by extracting and fusing a natural product, geldanamycin, and a natural substrate, ATP, were efficiently synthesized by the ring-closing metathesis assisted by the 2,4-dimethoxybenzyl group. This simpler scaffold design provides a practical synthesis of a set of analogs and demonstrates synthetic innovation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.094
• 作为产物：
  描述：

  3-溴丙烯 、 腺苷 在 二正丁基氧化锡 、 四丁基碘化铵 、 cesium fluoride 作用下， 以 甲醇 、 乙腈 为溶剂， 以21%的产率得到3'-O-allyl Adenosine
  参考文献：
  名称：

  Design and synthesis of 3′,5′-ansa-adenosines as potential Hsp90 inhibitors

  摘要：

  3',5'-Ansa-adenosine derivatives, rationally designed as an Hsp90 inhibitor by extracting and fusing a natural product, geldanamycin, and a natural substrate, ATP, were efficiently synthesized by the ring-closing metathesis assisted by the 2,4-dimethoxybenzyl group. This simpler scaffold design provides a practical synthesis of a set of analogs and demonstrates synthetic innovation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.094

文献信息

• Compositions and Methods for the Inhibition of Methyltransferases
  申请人：Northeastern University

  公开号：US20150057243A1

  公开（公告）日：2015-02-26

  Methods and compositions disclosed herein relate to detecting, analyzing, isolating and inhibiting methyltransferases, methyltransferase substrates, S-adenosyl-methionine-binding proteins and RNA, including for the treatment of disease.

  本文披露的方法和组合与检测、分析、分离和抑制甲基转移酶、甲基转移酶底物、S-腺苷甲硫氨酸结合蛋白和RNA有关，包括用于治疗疾病。
• 2' ,5' -Oligoadenylate analogs
  申请人：Koizumi Makoto

  公开号：US20050261235A1

  公开（公告）日：2005-11-24

  A 2-5A analog represented by the formula (1): wherein m is 0 or 1; n is 0 to 2; R 1 represents an alkoxy group having from 1 to 6 carbon atoms which may be substituted, an unprotected mercapto group, a mercapto group protected by a nucleic acid synthesis protecting group, or an alkylthio group having from 1 to 4 carbon atoms which may be substituted; R 2 , R 3 , R 4 , R 5 and R 6 represent an unprotected hydroxyl group, a hydroxyl group protected by a nucleic acid synthesis protecting group, an alkoxy group having from 1 to 6 carbon atoms which may be substituted, an unprotected mercapto group, a mercapto group protected by a nucleic acid synthesis protecting group, or an alkylthio group having from 1 to 4 carbon atoms which may be substituted; R 7 represents an oxygen atom, or a —O(CH 2 CH 2 O)q-group, wherein q is 2 to 6; R 8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms which may be substituted, or a 5′-phosphorylated oligonucleotide analog which has one hydroxyl group removed from the 5′-phosphoric acid group; E 1 , E 2 , E 3 and E 4 represent a naturally occurring or modified nucleic acid unit, or a pharmacologically acceptable salt thereof.

  一种由公式（1）表示的2-5A模拟物，其中m为0或1；n为0至2；R1表示具有1至6个碳原子的烷氧基，可以被取代，未保护的巯基，通过核酸合成保护基保护的巯基，或者具有1至4个碳原子的烷硫基，可以被取代；R2、R3、R4、R5和R6表示未保护的羟基，通过核酸合成保护基保护的羟基，具有1至6个碳原子的烷氧基，可以被取代，未保护的巯基，通过核酸合成保护基保护的巯基，或者具有1至4个碳原子的烷硫基，可以被取代；R7表示氧原子，或者-O(CH2CH2O)q-基团，其中q为2至6；R8表示氢原子，具有1至6个碳原子的烷基，可以被取代，或者从5'-磷酸基团中去除一个羟基的5'-磷酸寡核苷酸类似物；E1、E2、E3和E4表示天然或修饰的核酸单元，或其药理学上可接受的盐。
• AMINOOXY-MODIFIED NUCLEOSIDIC COMPOUNDS AND OLIGOMERIC COMPOUNDS PREPARED THEREFROM
  申请人：——

  公开号：US20030088079A1

  公开（公告）日：2003-05-08

  Nucleosidic monomers and oligomeric compounds prepared therefrom are provided which have increased nuclease resistance, substituent groups (such as 2′-aminooxy groups) for increasing binding affinity to complementary strand, and regions of 2′-deoxy-erythro-pentofuranosyl nucleotides that activate RNase H. Such oligomeric compounds are useful for diagnostics and other research purposes, for modulating the expression of a protein in organisms, and for the diagnosis, detection and treatment of other conditions susceptible to oligonucleotide therapeutics.

  提供了核苷酸单体和由此制备的寡聚物化合物，其具有增强的核酸酶抵抗性、取代基团（例如2'-氨氧基基团）以增加与互补链的结合亲和力，以及激活RNase H的2'-脱氧-红糖核苷酸区域。这种寡聚物化合物可用于诊断和其他研究目的，用于调节生物体内蛋白质的表达，并用于诊断、检测和治疗其他容易受到寡核苷酸治疗的疾病。
• Oligonucleotide analogs having modified dimers
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06420549B1

  公开（公告）日：2002-07-16

  Modified dimers having a ribose sugar moiety in the 5′ nucleoside and a 2′ modified sugar in the 3′ nucleoside are provided. The modified dimers are useful in the preparation of oligonucleotide analogs having enhanced properties compared to native oligonucleotides, including increased nuclease resistance, enhanced binding affinity and improved protein binding.

  提供了具有5'核苷酸里伯核糖基团和3'核苷酸2'修饰糖基的修饰二聚体。这些修饰二聚体可用于制备寡核苷酸类似物，与天然寡核苷酸相比具有增强性能，包括增加核酸酶抵抗力、增强结合亲和力和改善蛋白结合。
• Aminooxy-modified nucleosidic compounds and oligomeric compounds prepared therefrom
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06639062B2

  公开（公告）日：2003-10-28

  Nucleosidic monomers and oligomeric compounds prepared therefrom are provided which have increased nuclease resistance, substituent groups (such as 2′-aminooxy groups) for increasing binding affinity to complementary strand, and regions of 2′-deoxy-erythro-pentofuranosyl nucleotides that activate RNase H. Such oligomeric compounds are useful for diagnostics and other research purposes, for modulating the expression of a protein in organisms, and for the diagnosis, detection and treatment of other conditions susceptible to oligonucleotide therapeutics.

  提供了核苷酸单体和由此制备的寡核苷酸化合物，它们具有增强的核酸酶抵抗性、取代基团（如2'-氨氧基基团）以增加与互补链的结合亲和力，以及激活RNase H的2'-脱氧-赤藓糖核苷酸区域。这些寡核苷酸化合物可用于诊断和其他研究目的，用于调节生物体中蛋白质的表达，以及用于诊断、检测和治疗其他易感于寡核苷酸治疗的疾病。