9-(2-O-mesyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine | 110143-00-5

• 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: 9-(2-O-mesyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine
• 英文别名: 3'-O-mesylcordycepin；[(2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl] methanesulfonate
• CAS: 110143-00-5
• 化学式: C₁₁H₁₅N₅O₅S
• 分子量: 329.337
• InChiKey: RPOAICOYMLZFEU-MVKOHCKWSA-N

物化性质

• 沸点：
  697.1±65.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.97
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  142.45
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  9-(2-O-mesyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine 生成 [(2S,4S,5R)-5-(6-aminopurin-9-yl)-4-bromooxolan-2-yl]methanol
  参考文献：
  名称：

  HERDEWIJN, PIET;BALZARINI, JAN;BADA, MASANORI;PAUWELS, RUDI;VAN, AERSCHOT+, J. MED. CHEM., 31,(1988) N 10, C. 2040-2048

  摘要：

  DOI：
• 作为产物：
  描述：

  虫草素 在 吡啶 、 溶剂黄146 作用下， 反应 10.0h， 生成 9-(2-O-mesyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine
  参考文献：
  名称：

  各种2'-和3'-取代的2'，3'-二脱氧腺苷的合成及其抗HIV活性：结构活性分析。

  摘要：

  系统合成了2'，3'-二脱氧腺苷类似物，在糖部分的C-2或C-3的“上”或“下”位置取代了叠氮基，氟或羟基。针对人类免疫缺陷病毒（HIV）对MT-4细胞的细胞致病性评估了这些化合物。通过与叠氮化锂在甲磺酸酯3、2、5和4上进行亲核取代反应，合成了四个叠氮基衍生物6、7、8和9。（二乙基氨基）三氟化硫用于合成10-12。化合物13通过9-（3-氟-3-脱氧-β-D-木呋喃糖基）腺嘌呤的2'-脱氧获得。在叠氮基衍生物中，具有3'-叠氮基“向下”的化合物8的活性略高于2'，3'-二脱氧腺苷（1），但毒性更高，并且

  DOI：

  10.1021/jm00394a034

文献信息

• Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides
  作者：Piet Herdewijn、Jan Balzarini、Masanori Baba、Rudi Pauwels、Arthur Van Aerschot、Gerard Janssen、Erik De Clercq

  DOI：10.1021/jm00118a033

  日期：1988.10

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.
• Nucleic Acid Related Compounds. 91. Biomimetic Reactions Are in Harmony with Loss of 2‘-Substituents as Free Radicals (Not Anions) during Mechanism-Based Inactivation of Ribonucleotide Reductases. Differential Interactions of Azide, Halogen, and Alkylthio Groups with Tributylstannane and Triphenylsilane¹
  作者：Morris J. Robins、Stanislaw F. Wnuk、Amelia E. Hernández-Thirring、Mirna C. Samano

  DOI：10.1021/ja962117m

  日期：1996.1.1

  The initial step in the mechanism-based inactivation of ribonucleotide reductases by 2'-chloro-2'-deoxynucleotides is abstraction of H3' by a proximal free radical on the enzyme. The C3' radical is postulated to undergo spontaneous loss of chloride, and the resulting cationic radical loses a proton to give a 3'-keto intermediate. Successive beta-eliminations produce a Michael acceptor which causes inactivation. This hypothesis would predict rapid loss of mesylate or tosylate anions from C2', but sluggish loss of azide or thiomethoxide. in contrast, loss of azido and methylthio radicals from C2' should occur readily whereas homolysis to give (methyl or tolylsulfonyl)oxy and fluoro radicals should be energetically prohibitive. Protected 3'-O-(phenoxythiocarbonyl)-2'-substitute nucleosides were treated with tributylstannane/AIBN or triphenylsilane/dibenzoyl peroxide in refluxing toluene. The 2'-O-(mesyl and tosyl) and 2'-fluoro compounds underwent direct radical-mediated hydrogenolysis of the thionocarbonate group to give 3'-deoxy-2'-substituted products, whereas 2'-(azido, bromo, chloro, iodo, and methylthio)-3'-thionocarbonates gave 2',3'-didehydro-2',3'-dideoxy derivatives via loss of 2'-substituents from an incipient C3' radical. These results are in harmony with loss of radicals, but not anions, from C2'. The well-known radical-mediated hydrogenolytic cleavage of halogen and methylthio (slow) groups from C2' of the S'-hydroxy (unprotected) precursors and reduction of 2'-azides to amines occurred with tributylstannane/AIBN. Triphenylsilane/dibenzoyl peroxide gave parallel (but slower) hydrogenolysis with the 2'-(iodo, bromo, and methylthio) compounds, but cleavage of the 2'-chloro group was very slow and no reduction of 2'-azides to amines was detected. Rather, the latter system effected slow hydrogenolytic removal of the 2'-azido group. Thus, chemoselective differentiation of certain functional groups is possible with triphenylsilane and tributylstannane. Reduction of azides to amines with tributylstannane is known, but hydrogenolytic deazidation (slow) with triphenylsilane in the absence of amine formation appears to be novel.
• HERDEWIJN, PIET;BALZARINI, JAN;PAUWELS, RUDI;JANSSEN, GERARD;VAN, AERSCHO+, NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N, C. 1231-1257
  作者：HERDEWIJN, PIET、BALZARINI, JAN、PAUWELS, RUDI、JANSSEN, GERARD、VAN, AERSCHO+

  DOI：——

  日期：——
• HERDEWIJN, P.;PAUWELS, R.;BABA, M.;BALZARINI, J.;DE, CLERCQ E., J. MED. CHEM., 30,(1987) N 11, 2131-2137
  作者：HERDEWIJN, P.、PAUWELS, R.、BABA, M.、BALZARINI, J.、DE, CLERCQ E.

  DOI：——

  日期：——