8-(benzylamino)adenosine | 65456-83-9

• 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: 8-(benzylamino)adenosine
• 英文别名: Adenosine-derived inhibitor, 6；(2R,3R,4S,5R)-2-[6-amino-8-(benzylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 65456-83-9
• 化学式: C₁₇H₂₀N₆O₄
• 分子量: 372.384
• InChiKey: XBPUFDODTYBKPH-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  8-(benzylamino)adenosine 在 sodium 、 sodium naphthalenide 、 三苯基膦 、 丙酮 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 8,5'-imino-9-(5'-deoxy-2',3'-O-isopropylidene-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Minamoto, Katsumaro; Fujiki, Yasumi; Shiomi, Niro, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2337 - 2346

  摘要：

  DOI：
• 作为产物：
  描述：

  8-溴膘苷 生成 8-(benzylamino)adenosine
  参考文献：
  名称：

  SASAKI, TADASHI;MINAMOTO, KATSUMARO;FUJIKI, YASUMI;SHIOMI, NIRO;UDA, YORI+, 12TH SYMP. NUCL. ACIDS CHEM., KANAZAWA, OCT. 30 - NOV. 1, 1984, OXFORD; W+

  摘要：

  DOI：

文献信息

• Anti-HCV nucleoside derivatives
  申请人：——

  公开号：US20030008841A1

  公开（公告）日：2003-01-09

  The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。
• Exploiting Protein Conformational Change to Optimize Adenosine-Derived Inhibitors of HSP70
  作者：Matthew D. Cheeseman、Isaac M. Westwood、Olivier Barbeau、Martin Rowlands、Sarah Dobson、Alan M. Jones、Fiona Jeganathan、Rosemary Burke、Nadia Kadi、Paul Workman、Ian Collins、Rob L. M. van Montfort、Keith Jones

  DOI：10.1021/acs.jmedchem.5b02001

  日期：2016.5.26

  importance in oncology, this protein has become a popular target for drug discovery, efforts which have as yet brought little success. This study demonstrates that adenosine-derived HSP70 inhibitors potentially bind to the protein with a novel mechanism of action, the stabilization by desolvation of an intramolecular salt-bridge which induces a conformational change in the protein, leading to high affinity

  HSP70 是一种分子伴侣，是热休克反应的关键组成部分。由于其在肿瘤学中的重要性，这种蛋白质已成为药物发现的热门目标，但这些努力尚未取得成功。该研究表明，腺苷衍生的 HSP70 抑制剂可能以一种新的作用机制与蛋白质结合，通过分子内盐桥的去溶剂化来稳定化，从而诱导蛋白质的构象变化，从而产生高亲和力配体。我们还证明，通过这种机制的应用，可以以合理的方式优化腺苷衍生的 HSP70 抑制剂。
• SYSTEMATIC SYNTHESIS OF PURINE 8,5′-IMINO AND SUBSTITUTED IMINO CYCLONUCLEOSIDES
  作者：Tadashi Sasaki、Katsumaro Minamoto、Yasumi Fujiki

  DOI：10.1246/cl.1983.1017

  日期：1983.7.5

  To achieve a systematic synthesis of purine 8,5'-imino and substituted imino cyclonucleosides, 2',3'-O-isopropylidene-purinenucleosides substituted with a methylamino (4a,b), benzyl-amino (4c,d,g and h) and allylamino group (4e,f,i and j) at the C8 were synthesized. With these substrates in hand, extensive 8,5'-cyclization reactions were carried out using diphenyl carbonate/Et3N (Method A), N,N'-carbonyldiimidazole

  为了实现嘌呤 8,5'-亚氨基和取代亚氨基环核苷的系统合成，2',3'-O-异亚丙基-嘌呤核苷被甲氨基 (4a,b)、苄基氨基 (4c,d,g 和 h ) 和 C8 处的烯丙氨基 (4e,f,i 和 j) 被合成。使用这些底物，使用碳酸二苯酯/Et3N（方法 A）、N,N'-羰基二咪唑（方法 B）和 Mitsunobu 反应（方法 C）进行广泛的 8,5'-环化反应，得到 8,5 '-取代的亚氨基环核苷（5a、c、d、e、f和g）。方法C的环化产率一般高于其他两种方法。5a、b、c、d、e、f、g和h通过一或两步脱保护为相应的母体化合物8。在鸟苷系列中，一个新的循环系统包括一个 8,5'
• Identification of 8-Aminoadenosine Derivatives as a New Class of Human Concentrative Nucleoside Transporter 2 Inhibitors
  作者：Kazuya Tatani、Masahiro Hiratochi、Yoshinori Nonaka、Masayuki Isaji、Satoshi Shuto

  DOI：10.1021/ml500343r

  日期：2015.3.12

  Purine-rich foods have long been suspected as a major cause of hyperuricemia. We hypothesized that inhibition of human concentrative nucleoside transporter 2 (hCNT2) would suppress increases in serum urate levels derived from dietary purines. To test this hypothesis, the development of potent hCNT2 inhibitors was required. By modifying adenosine, an hCNT2 substrate, we successfully identified 8-aminoadenosine derivatives as a new class of hCNT2 inhibitors. Compound 12 moderately inhibited hCNT2 (IC50 = 52 +/- 3.8 mu M), and subsequent structure-activity relationship studies led to the discovery of compound 48 (IC50 = 0.64 +/- 0.19 mu M). Here we describe significant findings about structural requirements of 8-aminoadenosine derivatives for exhibiting potent hCNT2 inhibitory activity.
• Synthesis and structure-activity relationships of adenosine analogs as inhibitors of trypanosomal glyceraldehyde-3-phosphate dehydrogenase. Modifications at positions 5′ and 8
  作者：Alex M. Aronov、Michael H. Gelb

  DOI：10.1016/s0960-894x(98)00635-0

  日期：1998.12

  A number of 5', N6- and C8, N6-disubstituted adenosine analogs was synthesized and tested for inhibition of trypanosomal glyceraldehyde 3-phosphate dehydrogenase. The most active compound, N6-(3-methyl-2-butenyl)-8-(2-thienyl)adenosine, had Kl of 9 microM and was marginally selective for the parasite enzyme.