1,3-二去氮杂腺苷 | 20649-47-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 苯并咪唑核糖核苷和核糖核苷酸
• 中文名称: 1,3-二去氮杂腺苷
• 英文名称: 1,3-Dideazaadenosine
• 英文别名: 9-(1'-β-D-ribofuranosyl)-1,3-dideazaadenine；1-(4-amino-benzoimidazol-1-yl)-β-D-1-deoxy-ribofuranose；(2R,3R,4S,5R)-2-(4-aminobenzimidazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 20649-47-2
• 化学式: C₁₂H₁₅N₃O₄
• 分子量: 265.269
• InChiKey: DFNBVHDKNMLJFQ-HJQYOEGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-二去氮杂腺苷 在 吡啶 、 氯化亚砜 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 5'-chloro-5'-deoxy-9-(1'-β-D-ribofuranosyl)-1,3-dideazaadenine
  参考文献：
  名称：

  Synthesis and antimicrobial activity of some novel nucleoside analogues of adenosine and 1,3-dideazaadenosine

  摘要：

  A number of nucleoside analogues have been synthesized and evaluated for their antibacterial and antifungal activities against Staphylococcus aureus, Group D Streptococcus, Pseudomonas aeruginosa, Proteus spp., Salmonella spp., Aspergillus fumigates, Penicillium marneffei, Candida albicans, Cryptococcus neoformans, and Mucor spp. The compounds 1, 4, and 6 emerged as potent antibacterial agents with MIC values of 0.75, 0.38, and 0.19 mu M, respectively, against group D Streptococcus. Further, the results suggest that the molecules 4, 6, and 7 would be potent antifungal agents as they show substantial degree of inhibition toward the growth of pathogenic fungi with MICs of 0.75, 0.38, and 0.38 mu M, respectively. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.028
• 作为产物：
  描述：

  9-(1'-β-D-ribofuranosyl)-6-nitro-1,3-dideazaadenine 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 1,3-二去氮杂腺苷
  参考文献：
  名称：

  1-β-d-呋喃核糖基苯并咪唑3'，5'-磷酸酯的衍生物模拟腺苷3'，5'-磷酸酯（cAMP）和鸟苷3'，5'-磷酸酯（cGMP）的作用

  摘要：

  根据MNDO方法预测的性质，设计了一系列1-β-D-呋喃呋喃糖基苯并咪唑3'，5'-磷酸酯（cBIMP）的新类似物，并由取代的苯并咪唑合成。通过MNDO方法计算每个苯并咪唑碱基的偶极子向量以及HOMO和LUMO能量，并确定cBIMP衍生物的亲脂性。通常，cBIMP衍生物激活cAMP依赖性蛋白激酶I和II，并优先结合位点B，特别是对于II型激酶，其中2-三氟甲基-cBIMP和5,6-二氟-cBIMP表现出最高的位点选择性。每个cBIMP衍生物都可以刺激cGMP刺激的环磷酸二酯酶（cGS-PDE），其中5,6-二甲基-cBIMP与cGMP一样有效，并且还可以抑制cGMP抑制的磷酸二酯酶（cGI-PDE）。仅2-三氟甲基-cBIMP和Rp-硫代磷酸酯（cBIMPS）（赤道P = S）对cPDE的水解具有抗性。如果有的话，将Sp-硫代磷酸酯缓慢水解。除了表现出高亲脂性外，用于诱导细胞凋亡和抑制增殖

  DOI：

  10.1016/0008-6215(92)85050-a

文献信息

• Derivatives of 1-β-d-ribofuranosylbenzimidazole 3′,5′-phosphate that mimic the actions of adenosine 3′,5′-phosphate (cAMP) and guanosine 3′,5′-phosphate (cGMP)
  作者：Hans-Gottfried Genieser、Elisabeth Winkler、Elke Butt、Michaela Zorn、Susanne Schulz、Frank Iwitzki、Reinhold Störmann、Bernd Jastorff、Stein Ove Døskeland、Dagfinn Øgreid、Sandrine Ruchaud、Michel Lanotte

  DOI：10.1016/0008-6215(92)85050-a

  日期：1992.10

  A series of new analogues of 1-beta-D-ribofuranosylbenzimidazole 3',5'-phosphate (cBIMP) has been designed according to the properties predicted by the MNDO method, and synthesised from substituted benzimidazoles. Dipole vectors and HOMO and LUMO energies for each benzimidazole base were calculated by the MNDO method and the lipophilicities of the cBIMP derivatives were determined. In general, the

  根据MNDO方法预测的性质，设计了一系列1-β-D-呋喃呋喃糖基苯并咪唑3'，5'-磷酸酯（cBIMP）的新类似物，并由取代的苯并咪唑合成。通过MNDO方法计算每个苯并咪唑碱基的偶极子向量以及HOMO和LUMO能量，并确定cBIMP衍生物的亲脂性。通常，cBIMP衍生物激活cAMP依赖性蛋白激酶I和II，并优先结合位点B，特别是对于II型激酶，其中2-三氟甲基-cBIMP和5,6-二氟-cBIMP表现出最高的位点选择性。每个cBIMP衍生物都可以刺激cGMP刺激的环磷酸二酯酶（cGS-PDE），其中5,6-二甲基-cBIMP与cGMP一样有效，并且还可以抑制cGMP抑制的磷酸二酯酶（cGI-PDE）。仅2-三氟甲基-cBIMP和Rp-硫代磷酸酯（cBIMPS）（赤道P = S）对cPDE的水解具有抗性。如果有的话，将Sp-硫代磷酸酯缓慢水解。除了表现出高亲脂性外，用于诱导细胞凋亡和抑制增殖
• An Improved Procedure for the Synthesis of 1,3-Dideazaadenosine
  作者：Theresa A. Devlin、David J. Jebaratnam

  DOI：10.1080/00397919508011408

  日期：1995.3

  yield. The large scale monoreduction of 2,6-dinitroaniline, and the stannic chloride catalyzed glycosylation of 4 to obtain 6 as the only product (86%) are two important reactions in this five step synthesis.

  摘要 标题化合物的制备分五步完成，总产率为43%。2,6-二硝基苯胺的大规模单还原和氯化锡催化的 4 糖基化得到 6 作为唯一产物 (86%) 是这五步合成中的两个重要反应。
• Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine
  作者：Sarika Sinha、Richa Srivastava、Erik De Clercq、Ramendra K. Singh

  DOI：10.1081/ncn-200040614

  日期：2004.1.12

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.
• The nucleoside transport proteins, NupC and NupG, from Escherichia coli: specific structural motifs necessary for the binding of ligands
  作者：Simon G. Patching、Stephen A. Baldwin、Alexander D. Baldwin、James D. Young、Maurice P. Gallagher、Peter J. F. Henderson、Richard B. Herbert

  DOI：10.1039/b414739a

  日期：——

  unrelated transporters showed similar but distinct patterns of inhibition, revealing differing selectivities for the different nucleosides and their analogues. Binding of nucleosides to NupG required the presence of hydroxyl groups at each of the C-3' and C-5' positions of ribose, while binding to NupC required only the C-3' hydroxyl substituent. The greater importance of the ribose moiety for binding to

  测试了一系列46种天然核苷和类似物（主要是基于腺苷的）作为从大肠杆菌中富集的，与H（+）连接的核苷转运蛋白NupC和NupG吸收[U-（14）C]尿苷的抑制剂。这两个在进化上不相关的转运蛋白显示出相似但不同的抑制模式，揭示了对不同核苷及其类似物的不同选择性。核苷与NupG的结合需要在核糖的C-3'和C-5'位置分别存在羟基，而与NupC的结合仅需要C-3'羟基取代基。核糖部分对于结合NupG的重要性更高，与该蛋白质和寡糖之间的进化关系一致：运输者的主要促进者超家族（MFS）的H（+）同向转运蛋白（OHS）亚家族。对于两种蛋白质，C-3'处的天然α-构型和C-1'处的天然β-构型对于配体结合都是必需的。发现腺苷的咪唑环中的N-7和C-6的氨基对于结合并不重要，并且两个转运蛋白都显示出C-6 / N取代的灵活性。N-1和N-3中的一个或两个对腺苷类似物与NupC的结合很重要，但对NupG的结合
• Synthesis and antimicrobial activity of some novel nucleoside analogues of adenosine and 1,3-dideazaadenosine
  作者：Richa Srivastava、Anudita Bhargava、Ramendra K. Singh

  DOI：10.1016/j.bmcl.2007.09.028

  日期：2007.11

  A number of nucleoside analogues have been synthesized and evaluated for their antibacterial and antifungal activities against Staphylococcus aureus, Group D Streptococcus, Pseudomonas aeruginosa, Proteus spp., Salmonella spp., Aspergillus fumigates, Penicillium marneffei, Candida albicans, Cryptococcus neoformans, and Mucor spp. The compounds 1, 4, and 6 emerged as potent antibacterial agents with MIC values of 0.75, 0.38, and 0.19 mu M, respectively, against group D Streptococcus. Further, the results suggest that the molecules 4, 6, and 7 would be potent antifungal agents as they show substantial degree of inhibition toward the growth of pathogenic fungi with MICs of 0.75, 0.38, and 0.38 mu M, respectively. (C) 2007 Elsevier Ltd. All rights reserved.