2-(乙硫基)-9H-嘌呤-6-胺 | 33436-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-(乙硫基)-9H-嘌呤-6-胺
• 中文别名: 2-乙硫基腺嘌呤
• 英文名称: 2-ethylthioadenine
• 英文别名: 2-ethylsulfanyl-7H-purin-6-amine
• CAS: 33436-90-7
• 化学式: C₇H₉N₅S
• 分子量: 195.248
• InChiKey: OYUJKXQJBKRXFI-UHFFFAOYSA-N

物化性质

• 沸点：
  315.3±52.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-(乙硫基)-9H-嘌呤-6-胺 在 吡啶 、 甲醇 、 potassium permanganate 、 氨 作用下， 以 甲醇 、 硝基甲烷 、 溶剂黄146 为溶剂， 反应 67.0h， 生成 海绵核苷
  参考文献：
  名称：

  A Simple Method for Synthesis of Spongosine, Azaspongosine, and Their Antiplatelet Effects

  摘要：

  Reaction of 2-ethylthioadenine (1) with protected ribose (2) in the presence of stannic chloride gave 2-ethylthioadenosine (4). Oxidation of 5 with potassium permanganate yielded the corresponding sulfone (6) which furnished spongosine (2) after treatment with sodium methoxide. Similarly, reactions of 7-amino-5-ethylthio-1,2,3-triazolo[4,5-d]pyrimidine (8) with the ribose (2) gave 8-azaspongosine (13). The compounds (4) and 2 demonstrated potent antiaggregatory effects both in human platelet-rich plasma and whole blood, whereas, the aza analog (13) showed no inhibitory activity on platelet aggregation. Both (4) and (7) inhibit platelet aggregation in the presence of adenosine deaminase, whereas, adenosine is non-inhibitory, suggesting that analogs (4) and (7) are poor substrates for adenosine deaminase.

  DOI：

  10.1080/15257779508010711

文献信息

• [EN] IMPROVED SYNTHESIS OF 2-SUBSTITUTED ADENOSINES<br/>[FR] SYNTHESE AMELIOREE D'ADENOSINES SUBSTITUEES EN 2
  申请人：CAMBRIDGE BIOTECHNOLOGY LTD

  公开号：WO2005056571A1

  公开（公告）日：2005-06-23

  Synthesis of 2-substituted adenosines of formula (I) using 2-nitro pentabenzoyl adenosine, or 2-nitro pentaacetyl adenosine, as intermediate is described: Formula (I) wherein R = C1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), a benzyloxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-,cyano, nitro, C1-6 alkyl, or C1-6 alkoxy). The methods provide improved yield and purity of product.

  使用2-硝基戊二酰基腺苷或2-硝基戊醋酰基腺苷作为中间体，描述了合成式(I)的2-取代腺苷的方法：式(I)中，R = C1-6烷氧基（直链或支链）、苯氧基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）、苄氧基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）、或苯甲酰基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）。该方法提供了改善产物产量和纯度的效果。
• [EN] IMPROVED SYNTHESIS OF 2-SUBSTITUTED ADENOSINES<br/>[FR] SYNTHESE AMELIOREE D'ADENOSINES 2-SUBSTITUEES
  申请人：CAMBRIDGE BIOTECHNOLOGY LTD

  公开号：WO2005054269A1

  公开（公告）日：2005-06-16

  A method of synthesis of a 2-substituted adenosine of formula I which comprises converting a compound of formula II to a compound of formula (I), wherein: R is C 1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy), a benzyloxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, Cl_6 alkyl, or Cl_6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy); R' = H, or a protecting group.

  一种合成式I的2-取代腺苷的方法，包括将式II的化合物转化为式(I)的化合物，其中：R为C 1-6烷氧基（直链或支链）、苯氧基（未取代或经氟、氨基、CF3-、氰基、硝基、C 1-6烷基或C 1-6烷氧基单取代或双取代）、苄氧基（未取代或经氟、氨基、CF3-、氰基、硝基、Cl_6烷基或Cl_6烷氧基单取代或双取代）或苯甲酰基（未取代或经氟、氨基、CF3-、氰基、硝基、C 1-6烷基或C 1-6烷氧基单取代或双取代）；R' = H或保护基。
• Synthesis of 2-Substituted Adenosines
  申请人：Savory Edward Daniel

  公开号：US20080262214A1

  公开（公告）日：2008-10-23

  A method of synthesis of a 2-substituted adenosine of formula I which comprises converting a compound of formula II to a compound of formula (I), wherein: R is C 1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy), a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1_6 alkyl, or C1_6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy); R′═H, or a protecting group.

  一种合成式I的2-取代腺苷的方法，包括将式II的化合物转化为式(I)的化合物，其中：R为C1-6烷氧基（直链或支链）、苯氧基（未取代或经单、二取代的卤素、氨基、CF3-、氰基、硝基、C1-6烷基或C1-6烷氧基）、苯甲酰基（未取代或经单、二取代的卤素、氨基、CF3-、氰基、硝基、C1-6烷基或C1-6烷氧基）或苯丙酰基（未取代或经单、二取代的卤素、氨基、CF3-、氰基、硝基、C1-6烷基或C1-6烷氧基）；R′为H或保护基。
• Synthesis of 2-substituted adenosines
  申请人：Brown Giles Albert

  公开号：US20090131651A1

  公开（公告）日：2009-05-21

  Synthesis of 2-substituted adenosines of formula (I) using 2-nitro pentabenzoyl adenosine, or 2-nitro pentaacetyl adenosine, as intermediate is described: Formula (I) wherein R=C 1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF 3 —, cyano, nitro, C 1-4 alkyl, or C 1-4 alkoxy), a benzyloxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF 3 —, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF 3 —, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy). The methods provide improved yield and purity of product.

  本文描述了使用2-硝基戊酰基腺苷或2-硝基戊酰基腺苷作为中间体合成公式（I）的2-取代腺苷的方法： 公式（I）其中R=C1-6烷氧基（直链或支链）、苯氧基（未取代或单、双卤、氨基、CF3-,氰、硝基、C1-4烷基或C1-4烷氧基）、苄氧基（未取代或单、双卤、氨基、CF3-,氰、硝基、C1-6烷基或C1-6烷氧基）或苯甲酰基（未取代或单、双卤、氨基、CF3-,氰、硝基、C1-6烷基或C1-6烷氧基）。该方法提供了更高的产量和纯度的产物。
• Bhakuni, D. S.; Gupta, P. K.; George, C. X., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 5, p. 440 - 443
  作者：Bhakuni, D. S.、Gupta, P. K.、George, C. X.

  DOI：——

  日期：——