2-methylthio-N⁶-methyladenosine | 13406-51-4

• 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-methylthio-N⁶-methyladenosine
• 英文别名: 2-Methylmercapto-6-methylamino-9-β-D-ribofuranosyl-purin；N6-Methyl-2-methylthioadenosine；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-2-methylsulfanylpurin-9-yl]oxolane-3,4-diol
• CAS: 13406-51-4
• 化学式: C₁₂H₁₇N₅O₄S
• 分子量: 327.364
• InChiKey: PHFMCMDFWSZKGD-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  三乙胺 、 2-methylthio-N⁶-methyladenosine 在 吡啶 、 三氯硫磷 、 水 作用下， 反应 4.0h， 以63%的产率得到2-methylthio-N⁶-methyladenosine 5'-monothiophosphate bis-triethylammonium salt
  参考文献：
  名称：

  New highly active antiplatelet agents with dual specificity for platelet P2Y1 and P2Y12 adenosine diphosphate receptors

  摘要：

  Currently approved platelet adenosine diphosphate (ADP) receptor antagonists target only the platelet P2Y(12) receptor. Moreover, especially in patients with acute coronary syndromes, there is a strong need for rapidly acting and reversible antiplatelet agents in order to minimize the risk of thrombotic events and bleeding complications. In this study, a series of new P-1,P-4-di(adenosine-5') tetraphosphate (Ap(4)A) derivatives with modifications in the base and in the tetraphosphate chain were synthesized and evaluated with respect to their effects on platelet aggregation and function of the platelet P2Y(1), P2Y(12), and P2X1 receptors. The resulting structure activity relationships were used to design Ap(4)A analogs which inhibit human platelet aggregation by simultaneously antagonizing both P2Y(1) and P2Y(12) platelet receptors. Unlike Ap(4)A, the analogs do not activate platelet P2X1 receptors. Furthermore, the new compounds exhibit fast onset and offset of action and are significantly more stable than Ap(4)A to degradation in plasma, thus presenting a new promising class of antiplatelet agents. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.055
• 作为产物：
  描述：

  2-甲硫基腺苷 在 sodium acetate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 13.0h， 生成 2-methylthio-N⁶-methyladenosine
  参考文献：
  名称：

  New highly active antiplatelet agents with dual specificity for platelet P2Y1 and P2Y12 adenosine diphosphate receptors

  摘要：

  Currently approved platelet adenosine diphosphate (ADP) receptor antagonists target only the platelet P2Y(12) receptor. Moreover, especially in patients with acute coronary syndromes, there is a strong need for rapidly acting and reversible antiplatelet agents in order to minimize the risk of thrombotic events and bleeding complications. In this study, a series of new P-1,P-4-di(adenosine-5') tetraphosphate (Ap(4)A) derivatives with modifications in the base and in the tetraphosphate chain were synthesized and evaluated with respect to their effects on platelet aggregation and function of the platelet P2Y(1), P2Y(12), and P2X1 receptors. The resulting structure activity relationships were used to design Ap(4)A analogs which inhibit human platelet aggregation by simultaneously antagonizing both P2Y(1) and P2Y(12) platelet receptors. Unlike Ap(4)A, the analogs do not activate platelet P2X1 receptors. Furthermore, the new compounds exhibit fast onset and offset of action and are significantly more stable than Ap(4)A to degradation in plasma, thus presenting a new promising class of antiplatelet agents. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.055

文献信息

• [EN] NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS<br/>[FR] NOUVEAUX RÉACTIFS À BASE DE PHOSPHORE (V), LEURS PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION DANS LA FABRICATION DE COMPOSÉS ORGANOPHOSHOREUX (V) STÉRÉODÉFINIS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2019200273A1

  公开（公告）日：2019-10-17

  The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.

  本发明涉及新型磷（V）（P(V)）试剂，其制备方法以及利用这种新型试剂制备有机磷（V）化合物的方法。
• [EN] COMPOSITIONS AND METHODS FOR DELIVERY OF THERAPEUTIC AGENTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS PERMETTANT D'ADMINISTRER DES AGENTS THÉRAPEUTIQUES
  申请人：MODERNATX INC

  公开号：WO2017099823A1

  公开（公告）日：2017-06-15

  This disclosure provides improved lipid-based compositions, including lipid nanoparticle compositions, and methods of use thereof for delivering agents in vivo including nucleic acids and proteins. These compositions are not subject to accelerated blood clearance and they have an improved toxicity profile in vivo.

  这项披露提供了改进的基于脂质的组合物，包括脂质纳米粒子组合物，以及它们用于体内传递药剂的方法，包括核酸和蛋白质。这些组合物不受加速血清清除的影响，并且它们在体内具有改进的毒性特性。
• [EN] MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF<br/>[FR] MOLÉCULES D'ACIDE NUCLÉIQUE MODIFIÉES ET LEURS UTILISATIONS
  申请人：MODERNA THERAPEUTICS INC

  公开号：WO2014093924A1

  公开（公告）日：2014-06-19

  The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.

  本公开提供了经修改的核苷、核苷酸和核酸，以及它们的使用方法。
• SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS
  申请人：Arcturus Therapeutics, Inc.

  公开号：US20190002906A1

  公开（公告）日：2019-01-03

  This invention provides expressible polynucleotides, which can express a target protein or polypeptide. Synthetic mRNA constructs for producing a protein or polypeptide can contain one or more 5′ UTRs, where a 5′ UTR may be expressed by a gene of a plant. In some embodiments, a 5′ UTR may be expressed by a gene of a member of Arabidopsis genus. The synthetic mRNA constructs can be used as pharmaceutical agents for expressing a target protein or polypeptide in vivo.

  这项发明提供了可表达的多核苷酸，可以表达目标蛋白质或多肽。用于产生蛋白质或多肽的合成mRNA构建物可以包含一个或多个5' UTR，其中5' UTR可以由植物的基因表达。在某些实施例中，5' UTR可以由拟南芥属植物的基因表达。这些合成mRNA构建物可以用作体内表达目标蛋白质或多肽的药用剂。
• [EN] NOVEL ANTITHROMBOTIC DIADENOSINE TETRAPHOSPHATES AND RELATED ANALOGS<br/>[FR] NOUVEAUX DIADÉNOSINE TÉTRAPHOSPHATES ANTITHROMBOTIQUES ET ANALOGUES ASSOCIÉS
  申请人：GLSYNTHESIS INC

  公开号：WO2010059215A1

  公开（公告）日：2010-05-27

  The invention features compounds of formula I and methods of their use as antiplatelet and antithrombotic compounds: H /N=Qχ2 O O O O Λ Q2 — N, H R6/ N I f ) ( ^ XM O-Mγτ OM°τ X1MQ' ) r ( ^rf HO OH HO OQHi Nχi R2 Formula (I).

  这项发明涉及化合物的公式I和它们作为抗血小板和抗血栓化合物使用的方法：H /N=Qχ2 O O O O Λ Q2 — N, H R6/ N I f ) ( ^ XM O-Mγτ OM°τ X1MQ' ) r ( ^rf HO OH HO OQHi Nχi R2 公式(I)。