2-Methylmercapto-6-chloro-9β-(D-ribofuranosyl)-purine | 4105-32-2

• 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-Methylmercapto-6-chloro-9β-(D-ribofuranosyl)-purine
• 英文别名: 6-Chlor-2-methylthio-9-β-D-ribofuranosyl-purin；2-Methylthio-6-chloropurine riboside；(2R,3R,4S,5R)-2-(6-chloro-2-methylsulfanylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 4105-32-2
• 化学式: C₁₁H₁₃ClN₄O₄S
• 分子量: 332.768
• InChiKey: OAMKRDXWXFNNRI-KQYNXXCUSA-N

物化性质

• 熔点：
  182 °C
• 沸点：
  691.0±65.0 °C(Predicted)
• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 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：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-Methylmercapto-6-chloro-9β-(D-ribofuranosyl)-purine 在 ammonium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 (2R,3R,4S,5R)-2-(6-amino-2-(methylsulfinyl)-9H-purin-9-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  单碱基分辨率下 2-甲硫基-N6-异戊烯基腺苷的全转录组图谱

  摘要：

  已鉴定出数百个修饰碱基并进行酶促修饰以转移 RNA (tRNA) 以调节各种生物体中的 RNA 功能。2-甲硫基-N 6 -异戊烯基腺苷 (ms 2 i 6 A) 是一种在 tRNA 第 37 位发现的超修饰碱基，存在于原核生物和真核生物中。ms 2 i 6 A 传统上是通过使用 RNA 质谱法从总 RNA 中分离和消化每个 tRNA 来识别的。一种全转录组和单碱基分辨率方法，可实现 ms 2 i 6的绝对映射缺乏对其在不同 RNA 中分布的分析。在这里，通过化学选择性甲硫基生物偶联，我们引入了一种新方法（还原激活化学标记测序，ReACT-seq ）以单碱基分辨率检测全转录组 ms 2 i 6 A。利用甲硫基和氧氮丙啶基团之间的化学选择性，ms 2 i 6A 用叠氮基进行生物正交标记，不受规范核苷酸的干扰，从而在测序前促进甲硫基修饰的 RNA 的富集。ReACT-seq 在九个已知的 tRNA

  DOI：

  10.1021/jacs.2c13894
• 作为产物：
  描述：

  2-methylthio-6-chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine 在 氨 作用下， 以 乙醇 为溶剂， 生成 2-Methylmercapto-6-chloro-9β-(D-ribofuranosyl)-purine
  参考文献：
  名称：

  Photoinduced Alkylthiolation of Halogenated Purine Nucleosides

  摘要：

  描述了一种新的高效合成生物重要的甲基巯基嘌呤核苷的方法。该方法相较于早期报道的此类化合物的合成方法，具有显著的改进。

  DOI：

  10.1055/s-1986-31672

文献信息

• Substituted 6-(Benzylamino) Purine Riboside Derivatives, Use Thereof and Compositions Containing These Derivatives
  申请人：Szucova Lucie

  公开号：US20120071433A1

  公开（公告）日：2012-03-22

  The invention relates to 2-substituted-6-(substituted benzylamino)purine riboside derivatives of the general formula I. These compounds possess antiapoptotic, anti-inflammatory and differentiating activities. The invention relates also to the compositions, which contain these derivatives as active ingredients.

  该发明涉及一般式I的2-取代-6-(取代苯基氨基)嘌呤核苷衍生物。这些化合物具有抗凋亡、抗炎和分化活性。该发明还涉及包含这些衍生物作为活性成分的组合物。
• [EN] SUBSTITUTED 6-(BENZYLAMINO) PURINE RIBOSIDE DERIVATIVES, USE THEREOF AND COMPOSITIONS CONTAINING THESE DERIVATIVES<br/>[FR] DÉRIVÉS DE RIBOSIDE DE 6-BENZYLAMINOPURINE SUBSTITUÉE, LEURS UTILISATIONS ET COMPOSITIONS CONTENANT CES DÉRIVÉS
  申请人：UNIVERZITA PALACKEHO V OLOMOUC

  公开号：WO2010130233A1

  公开（公告）日：2010-11-18

  The invention relates to 2-substituted-6-(substituted benzylamino)purine riboside derivatives of the general formula I. These compounds possess antiapoptotic, anti-inflammatory and differentiating activities. The invention relates also to the compositions, which contain these derivatives as active ingredients. ˙

  该发明涉及一般式I的2-取代-6-(取代苄胺基)嘌呤核苷衍生物。这些化合物具有抗凋亡、抗炎和分化活性。该发明还涉及含有这些衍生物作为活性成分的组合物。
• Substituted 6-(Benzylamino) Purine Riboside Derivatives, Use Thereof and Compositions Containing These Derivatives
  申请人：Biopatterns, S.R.O

  公开号：US20140066394A1

  公开（公告）日：2014-03-06

  A method of treatment using 2-substituted-6-(substituted benzylamino)purine riboside derivatives of the general formula I. These compounds possess antiapoptotic, anti-inflammatory and differentiating activities.

  使用通式I的2-取代-6-(取代苯基氨基)嘌呤核苷衍生物的治疗方法。这些化合物具有抗凋亡、抗炎和分化活性。
• [EN] SUBSTITUTION DERIVATIVES OF N<6>-BENZYLADENOSINE, METHODS OF THEIR PREPARATION, THEIR USE FOR PREPARATION OF DRUGS, COSMETIC PREPARATIONS AND GROWTH REGULATORS, PHARMACEUTICAL PREPARATIONS, COSMETIC PREPARATIONS AND GROWTH REGULATORS CONTAINING THESE COMPOUNDS<br/>[FR] DERIVES DE SUBSTITUTION DE N<6>-BENZYLE ADENOSINE, METHODES DE PREPARATION ASSOCIEES, LEUR UTILISATION POUR REALISER DES MEDICAMENTS, DES PREPARATIONS COSMETIQUES ET DES REGULATEURS DE CROISSANCE ; PREPARATIONS PHARMACEUTIQUES, COSMETIQUES ET REGULATEURS DE CROISSANCE CONTENANT CES COMPOSES
  申请人：USTAV EX BOTAN AKADEMIE VED CE

  公开号：WO2004058791A3

  公开（公告）日：2004-10-28
• Anticancer activity of natural cytokinins: A structure–activity relationship study
  作者：Jiří Voller、Marek Zatloukal、René Lenobel、Karel Doležal、Tibor Béreš、Vladimír Kryštof、Lukáš Spíchal、Percy Niemann、Petr Džubák、Marián Hajdúch、Miroslav Strnad

  DOI：10.1016/j.phytochem.2010.04.018

  日期：2010.8

  Cytokinin ribosides (N(6)-substituted adenosine derivatives) have been shown to have anticancer activity both in vitro and in vivo. This study presents the first systematic analysis of the relationship between the chemical structure of cytokinins and their cytotoxic effects against a panel of human cancer cell lines with diverse histopathological origins. The results confirm the cytotoxic activity of N(6)-isopentenyladenosine, kinetin riboside, and N(6)-benzyladenosine and show that the spectrum of cell lines that are sensitive to these compounds and their tissues of origin are wider than previously reported. The first evidence that the hydroxylated aromatic cytokinins (ortho-, meta-, para-topolin riboside) and the isoprenoid cytokinin cis-zeatin riboside have cytotoxic activities is presented.Most cell lines in the panel showed greatest sensitivity to ortho-topolin riboside (IC(50) = 0.5-11.6 mu M). Cytokinin nucleotides, some synthesized for the first time in this study, were usually active in a similar concentration range to the corresponding ribosides. However, cytokinin free bases, 2-methylthio derivatives and both O- and N-glucosides showed little or no toxicity. Overall the study shows that structural requirements for cytotoxic activity of cytokinins against human cancer cell lines differ from the requirements for their activity in plant bioassays. The potent anticancer activity of ortho-topolin riboside (GI(50) = 0.07-84.60 mu M, 1st quartile = 0.33 mu M, median = 0.65 mu M, 3rd quartile = 1.94 mu M) was confirmed using NCI(60), a standard panel of 59 cell lines, originating from nine different tissues. Further, the activity pattern of oTR was distinctly different from those of standard anticancer drugs, suggesting that it has a unique mechanism of activity. In comparison with standard drugs, oTR showed exceptional cytotoxic activity against NCI(60) cell lines with a mutated p53 tumour suppressor gene. oTR also exhibited significant anticancer activity against several tumour models in in vivo hollow fibre assays. (C) 2010 Elsevier Ltd. All rights reserved.