海绵核苷 | 24723-77-1

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 海绵核苷
• 英文名称: 2-Methoxyadenosine
• 英文别名: (2R,3R,4S,5R)-2-(6-amino-2-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 24723-77-1
• 化学式: C₁₁H₁₅N₅O₅
• 分子量: 297.271
• InChiKey: AJACDNCVEGIBNA-KQYNXXCUSA-N

物化性质

• 沸点：
  705.0±70.0 °C(Predicted)
• 密度：
  1.98±0.1 g/cm3(Predicted)
• 熔点：
  193 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 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：
  149
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  海绵核苷 在 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Selective inhibition of TRPM2 channel by two novel synthesized ADPR analogues

  摘要：

  Transient receptor potential melastatin‐2 (TRPM2) channel critical for monitoring internal body temperature is implicated in the pathological processes such as neurodegeneration. However, lacking selective and potent TRPM2 inhibitors impedes investigation and validation of the channel as a drug target. To discover novel and selective TRPM2 inhibitors, a series of adenosine 5′‐diphosphoribose analogues were synthesized, and their activities and selectivity were evaluated. Whole‐cell patch‐clamp recordings were employed for screen and evaluation of synthesized compounds. Two compounds, 7i and 8a, were identified as TRPM2 inhibitors with IC50 of 5.7 and 5.4 μm, respectively. Both 7i and 8a inhibited TRPM2 current without affecting TRPM7, TRPM8, TRPV1 and TRPV3. These two TRPM2 inhibitors can serve as new pharmacological tools for further investigation and validation of TRPM2 channel as a drug target, and the summarized structure–activity relationship (SAR) may also provide insights into further improving existing inhibitors as potential lead compounds.

  DOI：

  10.1111/cbdd.13119
• 作为产物：
  描述：

  2,6-dimethoxy-9-(β-D-ribofuranosyl)-9H-purine 在 氨 作用下， 以 水 为溶剂， 反应 26.0h， 以61%的产率得到海绵核苷
  参考文献：
  名称：

  [EN] IMPROVED SYNTHESIS OF 2-SUBSTITUTED ADENOSINES
  [FR] SYNTHESE AMELIOREE D'ADENOSINES 2-SUBSTITUEES

  摘要：

  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。

  公开号：

  WO2005054269A1

文献信息

• Synthesis and pharmacological evaluation of a series of analogs of 1-methylisoguanosine
  作者：Robert T. Bartlett、Alan F. Cook、Michael J. Holman、Warren W. McComas、Eugene F. Nowoswait、Mohindar S. Poonian、Judy A. Baird-Lambert、Brian A. Baldo、John F. Marwood

  DOI：10.1021/jm00140a007

  日期：1981.8

  Modification at the 5' position yielded the deoxy, iodo, and phosphate derivatives 15, 13, and 16, as well as the cyclic 3',5'-phosphate 17. The synthesis of the C-nucleoside analogue 19 was achieved from the beta-D-ribofuranosylcarboximidic ester 20. The acyclic analogue 29 and the beta-D-arabinofuranosyl derivative 35 were both synthesized by reaction of methyl isocyanate with the appropriately protected

  在肌肉松弛剂，心血管，抗炎和抗过敏试验中，评估了具有药理活性的海洋天然产物1-甲基异鸟苷（1）的一系列类似物的生物活性。在1位上的修饰分别产生乙基，正丁基，正辛基和苯基衍生物3-6。在8位的取代提供了溴，肼和氨基化合物9-11。在5'位的修饰产生了脱氧，碘和磷酸盐衍生物15、13和16，以及环状3'，5'-磷酸盐17。C-核苷类似物19的合成由β完成-D-呋喃核糖基羧酰亚胺酯20。无环类似物29和β-D-阿拉伯呋喃糖基衍生物35都是通过异氰酸甲酯与适当保护的氨基氰咪唑前体28和32反应合成的。1-甲基黄嘌呤（12），异鸟苷（7）和2-甲氧基腺苷（18）。也被合成。在高达100 mg / kg po的剂量下，5'-磷酸16，环状3'，5'-磷酸17和O-甲基化的类似物2-甲氧基腺苷18在产生肌肉松弛和体温过低方面具有活性。这些化合物具有抗过敏活性，并且与1-乙基（3）和1-正丁基（4）类似物
• Anti-HCV nucleoside derivatives
  申请人：——

  公开号：US20030008841A1

  公开（公告）日：2003-01-09

  The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。
• [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。
• FORMATION OF 2?-DEOXY-2-NITROADENOSINES BY REACTION OF 2?-DEOXYADENOSINES WITH COPPER(II) NITRATE/ACETIC ANHYDRIDE
  作者：Toyo Kaiya、Haruko Tanaka、Kohfuku Kohda

  DOI：10.1081/ncn-120014815

  日期：——

  ABSTRACT Nitration of 9-substituted [ethyl, (Ac)2-2′-deoxyribosyl, (Ac)3-ribosyl] N 6-acetyladenine derivatives with Cu(NO3)2·3H2O/Ac2O was examined. Nitration proceeded at the 2-position, although the yield was low. Removal of the acetyl groups gave 2′-deoxy-2-nitroadenosine derivatives.

  摘要 研究了 9-取代的 [乙基，(Ac)2-2'-脱氧核糖基，(Ac)3-核糖基]N 6-乙酰腺嘌呤衍生物与 Cu(NO3)2·3H2O/Ac2O 的硝化反应。尽管产率低，但硝化作用在 2 位进行。去除乙酰基得到 2'-脱氧-2-硝基腺苷衍生物。
• [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。

表征谱图