2-pentylthioadenosine | 50823-24-0

• 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-pentylthioadenosine
• 英文别名: 2-Amylthioadenosine；(2R,3R,4S,5R)-2-(6-amino-2-pentylsulfanylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 50823-24-0
• 化学式: C₁₅H₂₃N₅O₄S
• 分子量: 369.445
• InChiKey: YEELQEVZYSNSHF-IDTAVKCVSA-N

物化性质

• 熔点：
  177 °C (decomp)
• 沸点：
  720.5±70.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-pentylthioadenosine 在 吡啶 、 三氯硫磷 、 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 P¹,P⁴-di-(2-pentylthio-5'-adenosine)-P¹,P⁴-dithio-P²,P³-chloromethylenetetraphosphate sodium 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：

  5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamidoxime 在 ammonium sulfide 、 sodium dithionite 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成 2-pentylthioadenosine
  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 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)。
• ATP analogues
  申请人：Astra Pharmaceuticals Limited

  公开号：EP0508687B1

  公开（公告）日：1995-09-13
• ATP ANALOGUES
  申请人：FISONS plc

  公开号：EP0579643A1

  公开（公告）日：1994-01-26
• NOVEL ANTITHROMBOTIC DIADENOSINE TETRAPHOSPHATES AND RELATED ANALOGS
  申请人：Glsynthesis Inc.

  公开号：EP2364086A1

  公开（公告）日：2011-09-14
• US5654285A
  申请人：——

  公开号：US5654285A

  公开（公告）日：1997-08-05