N⁶,N⁶,2'-O,5'-O-tetrabenzoyl-3'-deoxyadenosine | 66884-45-5

• 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: N⁶,N⁶,2'-O,5'-O-tetrabenzoyl-3'-deoxyadenosine
• 英文别名: (2R,3R,5S)-2-[6-(N-benzoylbenzamido)-9H-purin-9-yl]-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate；N⁶,N⁶,O^2'_,O5'-tetrabenzoyl-3'-deoxy-adenosine；N⁶,N⁶,O^2'_,O5'-Tetrabenzoyl-3'-desoxy-adenosin；3'-deoxy-tetrabenzoyl adenosine；[(2S,4R,5R)-4-benzoyloxy-5-[6-(dibenzoylamino)purin-9-yl]oxolan-2-yl]methyl benzoate
• CAS: 66884-45-5
• 化学式: C₃₈H₂₉N₅O₇
• 分子量: 667.678
• InChiKey: BVFOFCUCKPHAFL-NHRDYHFISA-N

物化性质

• 沸点：
  847.1±75.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N⁶,N⁶,2'-O,5'-O-tetrabenzoyl-3'-deoxyadenosine 在 吡啶 、 sodium hydroxide 作用下， 以 吡啶 、 甲醇 、 乙醇 为溶剂， 反应 28.25h， 生成 N⁶-benzoyl-3'-deoxy-5'-O-(monomethoxytrityl)adenosine 2'-<2,5-dichlorophenyl 2-(p-nitrophenyl)ethyl phosphate>
  参考文献：
  名称：

  核苷酸。第二十八部分。2'-5'-cordycepin-trimer核的化学合成†

  摘要：

  3'-脱氧腺苷-（2'-5'）-3'-脱氧腺苷基-（2'-5'）-3'-脱氧腺苷（30；三聚虫草素）的化学合成通过使用不同保护基团的三种不同途径进行描述并应用磷酸三酯方法。中间体已通过元素分析和光谱学手段进行了分离和表征。通过脱保护获得了高收率的30，使得该具有生物学活性的化合物可以制备规模获得。

  DOI：

  10.1002/hlca.19870700808
• 作为产物：
  描述：

  腺苷 在 吡啶 、 2-乙酰氧基异丁酰溴 、 三乙基硼氢化锂 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 3.0h， 生成 N⁶,N⁶,2'-O,5'-O-tetrabenzoyl-3'-deoxyadenosine
  参考文献：
  名称：

  Structure–Activity Relationships of Synthetic Cordycepin Analogues as Experimental Therapeutics for African Trypanosomiasis

  摘要：

  Novel methods for treatment of African trypanosomiasis, caused by infection with Trypanosoma brucei are needed. Cordycepin (3'-deoxyadenosine, la) is a powerful trypanocidal compound in vitro but is ineffective in vivo because of rapid metabolic,degradation by adenosine deaminase (ADA). We elucidated the structural moieties of cordycepin required for trypanocidal activity and designed analogues that retained trypanotoxicity while gaining resistance to ADA-mediated metabolism. 2-Fluorocordycepin (2-fluoro3'-deoxyadenosine, 1b) was identified as a selective, potent, and ADA-resistant trypanocidal compound that cured T. brucei infection in mice. Compound 1b is transported through the high affinity TbAT1/P2 adenosine transporter and is a substrate of T. b. brucei adenosine kinase. 1b has good preclinical properties suitable for an, oral drug, albeit a relatively short plasma half-life. We present a rapid and efficient synthesis of 2-halogenated cordycepins, also useful synthons. for the development of additional novel C2-substituted 3'-deoxyadenosine analogues to be evaluated in development of experimental therapeutics.

  DOI：

  10.1021/jm401530a

文献信息

• Synthesis and properties of 3′-deoxyadenylate trimer dA2′p5′A2′p5′A
  作者：Ramamurthy Charubala、Wolfgang Pfleiderer

  DOI：10.1016/0040-4039(80)88070-1

  日期：1980.1

  The trimeric 3′-deoxyadenylyl-(2′→5′)-3′-deoxyadenylyl-(2′→5′)-3′-deoxyadenosine () was synthesized via the phosphotriester approach starting from cordycepine (). Various physical data have been determined and compared with those of the ribo-A2′p5′A2′p5′A analog.

  从虫草素（）开始，通过磷酸三酯法合成了三聚体3'-脱氧腺苷基-（2'→5'）-3'-脱氧腺苷基-（2'→5'）-3'-脱氧腺苷（）。已经确定了各种物理数据，并将其与ribo-A2'p5'A2'p5'A类似物的数据进行了比较。
• Therapeutic compounds
  申请人：Higginbottom Michael

  公开号：US20080076776A1

  公开（公告）日：2008-03-27

  Compounds of formula (I) below are disclosed. Their use as medicaments is described, in particular for the treatment of pain or inflammation: wherein: when X═Y=Z=OH, R 1 is OCH 2 CF 2 CF 3 , phenoxy (substituted with 3-(4-trifluoromethylphenyl), 3,4-dichloro, (3-trifluoromethyl,4-fluoro), (3-trifluoromethyl,4-chloro), (3-chloro, 4-cyano), or 3,5-bis(trifluoromethyl)), 1-piperazinyl(4-(3,4-dichlorophenyl)), phenyl (substituted with 3,4-dichloro, 3,5-difluoro, 3,5-bis(trifluoromethyl) or 3,4,5-trifluoro) or 2-benzofuranyl; or when X═Y═OH and Z=OMe, R 1 is OCH 3 , OCH 2 CHF 2 , OCH 2 cyclopentyl, O-(2,5-difluorophenyl) or (S)-sec-butylamino; or when X═H and Y=Z=OH, R 1 is n-hexylamino or cyclopentylamino; or when (IV) X=Z=OH and Y═H, R 1 is cyclopentylamino; or a pharmaceutically acceptable salt thereof.

  公开了以下式子（I）的化合物。它们的用途作为药物被描述，特别是用于治疗疼痛或炎症：其中：当X═Y=Z=OH，R1为OCH2CF2CF3，苯氧（用3-(4-三氟甲基苯基)、3,4-二氯、(3-三氟甲基，4-氟)、(3-三氟甲基，4-氯)、(3-氯，4-氰基)或3,5-双(三氟甲基)取代的），1-哌嗪基(4-(3,4-二氯苯基))，苯基（用3,4-二氯、3,5-二氟、3,5-双(三氟甲基)或3,4,5-三氟取代的）或2-苯并呋喃基；或当X═Y═OH且Z=OMe，R1为OCH3，OCH2CHF2，OCH2环戊基，O-(2,5-二氟苯基)或(S)-sec-丁基氨基；或当X═H且Y=Z=OH，R1为正己基氨基或环戊基氨基；或当（IV）X=Z=OH且Y═H，R1为环戊基氨基；或其药学上可接受的盐。
• [EN] ADENOSINE RECEPTOR AGONISTS<br/>[FR] COMPOSES THERAPEUTIQUES
  申请人：CAMBRIDGE BIOTECHNOLOGY LTD

  公开号：WO2005084653A3

  公开（公告）日：2006-05-18
• WO2008/745
  申请人：——

  公开号：——

  公开（公告）日：——
• Bentley et al., Journal of the Chemical Society, 1951, p. 2301,2304
  作者：Bentley et al.

  DOI：——

  日期：——