2',3'-O-isopropylidene-5'-O-(4-nitrophenoxycarbonyl)adenosine

• 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: 2',3'-O-isopropylidene-5'-O-(4-nitrophenoxycarbonyl)adenosine
• 英文别名: 2’,3‘-O-isopropylidene-5‘-O-(4-nitrophenoxycarbonyl)adenosine；[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl (4-nitrophenyl) carbonate
• 化学式: C₂₀H₂₀N₆O₈
• 分子量: 472.414
• InChiKey: ABKJCKZSEOLANO-SCFUHWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2',3'-O-isopropylidene-5'-O-(4-nitrophenoxycarbonyl)adenosine 在 甲酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 25.25h， 生成 5'-(N-methyl)carboxamidoadenosine
  参考文献：
  名称：

  Identification of 8-Aminoadenosine Derivatives as a New Class of Human Concentrative Nucleoside Transporter 2 Inhibitors

  摘要：

  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.

  DOI：

  10.1021/ml500343r
• 作为产物：
  描述：

  腺苷 在 对甲苯磺酸 、 N,N-二异丙基乙胺 、 原甲酸三甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 2',3'-O-isopropylidene-5'-O-(4-nitrophenoxycarbonyl)adenosine
  参考文献：
  名称：

  通过UV / Vis光解离作用光谱表征的气相带电荷标记的DNA自由基。

  摘要：

  带有固定电荷基团的腺苷自由基在气相中生成，并通过串联质谱，氘标记和UV / Vis作用谱进行结构表征。实验结果与Born-Oppenheimer分子动力学，从头算和激发态计算相结合，导致腺苷自由基作为N-7氢原子加合物的明确分配。发现带电荷标签的自由基在电子学上等同于天然DNA核苷自由基。

  DOI：

  10.1002/anie.201916493

文献信息

• [EN] SYNTHETIC ANTIGENS FOR TUBERCULOSIS DETECTION<br/>[FR] ANTIGÈNES SYNTHÉTIQUES POUR LA DÉTECTION DE LA TUBERCULOSE
  申请人：KEI INTERNATIONAL LTD

  公开号：WO2020030034A1

  公开（公告）日：2020-02-13

  Provided herein are a synthetic antigen and a solid substrate comprising an antigen immobilized thereto and a method for immobilizing said antigen onto a solid substrate. Provided herein are also a biosensor and tuberculosis detection system comprising said solid substrate. Provided herein is also a method of detecting the presence of antibodies against mycobacterial material in a sample using said synthetic antigen or solid substrate.

  本文提供了一种合成抗原和固体基质，包括固定在其上的抗原以及将该抗原固定在固体基质上的方法。本文还提供了一种生物传感器和结核病检测系统，包括所述固体基质。本文还提供了一种使用所述合成抗原或固体基质检测样品中抗结核杆菌物质抗体存在的方法。
• Conjugation of Adenosine and Hexa-(<scp>d</scp>-arginine) Leads to a Nanomolar Bisubstrate-Analog Inhibitor of Basophilic Protein Kinases
  作者：Erki Enkvist、Darja Lavogina、Gerda Raidaru、Angela Vaasa、Indrek Viil、Marje Lust、Kaido Viht、Asko Uri

  DOI：10.1021/jm0605942

  日期：2006.11.30

  Conjugates of oligoarginine peptides with adenine, adenosine, adenosine-5'-carboxylic acid, and 5-isoquino-linesulfonic acid were synthesized and characterized as bisubstrate-analog inhibitors of cAMP-dependent protein kinase. Adenosine and adenine derivatives were connected to the N- or C-terminus of peptides containing four to six L- or D-arginine residues via a linker with a length that had been optimized in structure-activity studies. The orientation of the peptide chain strongly affected the activity of compounds incorporating D-arginines. The biligand inhibitor containing Hidaka's H9 isoquinolinesulfonamide connected to the L- peptide had 65 times higher potency than the corresponding adenosine-containing conjugate, while both types of the conjugate comprising D-peptides had similar low nanomolar activity. Two of the most active adenosine-and H9-peptide conjugates were tested in the panel of 52 different kinases. At 1 mu M concentration, both compounds showed strong (more than 95%) inhibition of several basophilic AGC kinases, including pharmaceutically important kinases ROCK II and PKB/Akt.
• BISUBSTRATE FLUORESCENT PROBE BINDING TO PROTEIN KINASES
  申请人：Uri Asko

  公开号：US20100233743A1

  公开（公告）日：2010-09-16

  This invention relates to fluorescent probes for identification of compounds binding to protein kinases, for measurement of the affinity of inhibitors of protein kinases, and determination of the active concentration of protein kinases binding to the probe. Bisubstrate-analog character of the probe enables the simultaneous evaluation of inhibitors targeted to both ATP binding site and/or substrate protein/peptide binding domain of the kinase. High affinity of the probe (K d =1.0 nM towards cAMP-dependent protein kinase) affords the application of the enzymes at low concentration which leads to the substantial decrease of the consumption of the kinase. Due to the ability of the conjugates of oligo(D-arginine) with a ATP binding site targeted inhibitors of this invention to bind with high affinity to a wide spectrum of (basophilic) kinases, a single Fluorescent probe is applicable for assessment of inhibitory potency of compounds towards a great number of protein kinases.
• SYNTHETIC ANTIGENS FOR TUBERCULOSIS DETECTION
  申请人：KEI INTERNATIONAL LIMITED

  公开号：US20210293804A1

  公开（公告）日：2021-09-23

  Disclosed is a synthetic antigen and a solid substrate having an antigen immobilized thereto and a method for immobilizing the antigen onto a solid substrate. Also disclosed is a biosensor and tuberculosis detection system employing the said solid substrate. Also disclosed is a method of detecting the presence of antibodies against mycobacterial material in a sample using the synthetic antigen or solid substrate.
• US8158376B2
  申请人：——

  公开号：US8158376B2

  公开（公告）日：2012-04-17