3-(2-deoxy-β-D-erythro-pentofuranosyl)-7-nitro-3H-imidazo<4,5-b>pyridine | 133832-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 3-(2-deoxy-β-D-erythro-pentofuranosyl)-7-nitro-3H-imidazo<4,5-b>pyridine
• 英文别名: 9-(2-deoxy-β-D-ribofuranosyl)-1-deazapurine；7-nitro-3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo<4,5-b>pyridine；7-nitro-3-(2'-deoxy-β-D-ribofuranosyl)imidazo[4,5-b]pyridine；3-(2-Deoxy-beta-D-erythro-pentofuranosyl)-7-nitro-3H-imidazo[4,5-B]pyridine；(2R,3S,5R)-2-(hydroxymethyl)-5-(7-nitroimidazo[4,5-b]pyridin-3-yl)oxolan-3-ol
• CAS: 133832-65-2
• 化学式: C₁₁H₁₂N₄O₅
• 分子量: 280.24
• InChiKey: OBUURYVQHCHXFM-DJLDLDEBSA-N

物化性质

• 沸点：
  614.1±65.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(2-deoxy-β-D-erythro-pentofuranosyl)-7-nitro-3H-imidazo<4,5-b>pyridine 在 Raney-Ni catalyst 三甲基氯硅烷 、 氢气 、 一水合肼 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 5.25h， 生成 7-(benzoylamino)-3-<2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl>-3H-imidazo<4,5-b>pyridine
  参考文献：
  名称：

  Hoogsteen -Duplex DNA：含有1-deaza-2'-deoxyadenosine的寡核苷酸的合成和碱基配对

  摘要：

  含有1脱氮-2'-脱氧腺苷寡脱氧核糖核苷酸（= 7-氨基-3-（2-脱氧β-D-赤式-pentofuranosyl）-3 ħ -咪唑并[4，5- b ]吡啶;图1b）形成的Hoogsteen双链体。由于不存在N（1），因此无法建立Watson - Crick碱基对。对于这些研究，寡核苷酸构件-膦酸酯3A和亚磷酰胺3B -从制备1B通过图4a和5，以及在Fractosil -连接的6B，并在固相合成中使用。各种适用性还研究了N保护基（参见4a – c）。所述的Hoogsteen双工d [（C 1名A）20 ]·d（T 20）（11·13 ; Ť米15°）比d（A稳定少20）·d（T 20）（12·13 ;吨米60°）。嵌段低聚物d（[c 1 A）10 –; T 10 ]（14）和d [T 10-（c 1 A）10 ]（15）在同一链中含有嘌呤和嘧啶碱基的）也能够彼此形成双链体。发现链极性是平行的。

  DOI：

  10.1002/hlca.19940770604
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 盐酸 、 氨 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 丙酮 、 乙腈 、 mineral oil 为溶剂， 反应 0.67h， 生成 3-(2-deoxy-β-D-erythro-pentofuranosyl)-7-nitro-3H-imidazo<4,5-b>pyridine
  参考文献：
  名称：

  核酸基团和羧酸盐基团的辅助配位对氨基酸核苷磷酸氨基磷酸酯水解的影响

  摘要：

  核苷氨基磷酸酯（NPs）是一类核苷酸类似物，已被开发为潜在的抗病毒/抗肿瘤前药。最近，我们发现某些氨基酸核苷氨基磷酸酯（aaNPs）可以充当病毒聚合酶（如HIV-1 RT）的底物。在这里，我们报告了一系列新的aaNPs的合成和水解，这些aaNPs包含天然或修饰的核碱基，以定义其差异反应性的基础。在不同溶液pD值（5-7）和温度下，通过NMR光谱学研究了水的稳定性，动力学和水解途径。观察到动力学和机理（PN和/或P水解反应的O键裂解在很大程度上取决于核碱基和氨基酸部分的性质。发现天冬氨酰NPs比Gly或β-AlaNPs更具反应性。对于天冬氨酰NP，核碱基的反应顺序为1-去氮杂腺嘌呤> 7-去氮杂腺嘌呤>腺嘌呤>胸腺嘧啶≥3-去氮杂腺嘌呤。值得注意的是，即使在4°C下，Asp-1-deaza-dAMP的中性水溶液也会通过专有的PO键水解而自发降解（Asp-1-deaza-dAMP与Asp

  DOI：

  10.1002/chem.201102279

文献信息

• Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells
  作者：Ivan Votruba、Antonín Holý、Hana Dvořáková、Jaroslav Günter、Dana Hocková、Hubert Hřebabecký、Tomas Cihlar、Milena Masojídková

  DOI：10.1135/cccc19942303

  日期：——

  Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs. All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N⁹-isomers in the purine and N¹-isomers in the pyrimidine series. Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety. The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N⁷-nitrogen atom. On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives. Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed. The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-dideoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-dideoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.

  藻酸盐凝胶包埋的辅助胸腺嘧啶依赖菌株大肠杆菌细胞催化2'-脱氧尿嘧啶的2-脱氧-D-核糖呋喃基团转移到嘌呤和嘧啶碱基以及它们的氮杂和去氮类似物。所有实验都不可避免地产生β-异构体；在大多数情况下，反应是区域特异性的，产生嘌呤中的N⁹-异构体和嘧啶系列中的N¹-异构体。此外，2,3-二脱氧核苷酸可以作为糖基团的供体。嘌呤碱基的受体活性仅在取代上有少许影响，唯一的条件是存在N⁷-氮原子。另一方面，在嘧啶系列中，活性仅限于大多数短链5-烷基和5-卤代尿嘧啶衍生物的狭窄选择。含氨基的杂环碱基会发生脱氨作用；可以通过将碱基转化为相应的N-二甲氨基甲烯基衍生物来避免这种情况，然后进行氨解作用。该方法通过分离腺嘌呤、鸟嘌呤、2-氯腺嘌呤、6-甲基嘌呤、8-氮杂腺嘌呤、8-氮杂鸟嘌呤、1-去氮腺嘌呤、3-去氮腺嘌呤的9-(2-脱氧-β-D-核糖呋喃基)衍生物，5-乙基尿嘧啶、5-氟尿嘧啶的1-(2-脱氧-β-D-核糖呋喃基)衍生物，以及9-(2,3-二脱氧-β-D-戊呋喃基)缺氧嘌呤、9-(2,3-二脱氧-β-D-戊呋喃基)-6-甲基嘌呤和其他核苷酸的验证。
• Purine and 1-deazapurine ribonucleosides and deoxyribonucleosides: synthesis and biological activity
  作者：Gloria Cristalli、Sauro Vittori、Alessandra Eleuteri、Mario Grifantini、Rosaria Volpini、Giulio Lupidi、Laura Capolongo、Enrico Pesenti

  DOI：10.1021/jm00111a044

  日期：1991.7

  6-hydroxylamino derivatives of 1-deazapurine 9, 12, and 17 and also the blocked compound 13 are inhibitors of ADA whereas the purine derivatives 4 and 6 and the nitro compounds 11 and 16 are resistant to the enzyme. 7-(Hydroxylamino)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3H-imi dazo[4,5- b]pyridine, the less cytotoxic but the most active ADA inhibitor in the series (Ki = 2.7 x 10(-7)), greatly potentiates

  合成了一系列6-（羟氨基）嘌呤和-1-脱氮嘌呤核苷，并测试了它们的抗肿瘤和腺苷脱氨酶抑制活性。所有检查的分子均显示出与参考化合物6-（羟基氨基）-9-β-D-呋喃呋喃糖基嘌呤（HAPR）和ara-A相当的体外活性，其ID50为0.9 microM至约100 microM。1-脱氮嘌呤9、12和17的6-羟基氨基衍生物以及被保护的化合物13是ADA的抑制剂，而嘌呤衍生物4和6以及硝基化合物11和16对该酶具有抗性。7-（羟氨基）-3-（2-脱氧-β-D-赤-戊呋喃糖基）-3H-咪唑并[4,5-b]吡啶，细胞毒性较小，但是该系列中活性最高的ADA抑制剂（Ki = 2.7 x 10（-7）），可大大增强ara-A的体外抗肿瘤活性。
• Synthesis of 6-Substituted 1-Deazapurine 2?-Deoxyribonucleosides
  作者：Thomas Wenzel、Frank Seela

  DOI：10.1002/hlca.19960790117

  日期：1996.2.7

  The synthesis of 6-substituted 1-deazapurine 2′-deoxyribonucleosides is described. Glycosylation of the 1-deazapurine (imidazo[4,5-b]pyridine) anions with the α-D-halogenose 5 gives stereoselectively N7- and N9- regioisomers. 1H-NMR NOE and 13C-NMR spectroscopy are used for unambiguous assignment of isomers, and 15N-NMR chemical shifts are correlated with σparaHammett constants and point charges.

  描述了6-取代的1-脱氮嘌呤2'-脱氧核糖核苷的合成。1-脱氮嘌呤（咪唑并[4,5-的糖基化b与α-d-halogenose]吡啶）阴离子5给出了立体选择性Ñ 7 -和Ñ 9 -区域异构体。1个H-NMR和NOE 13 C-NMR光谱法被用于异构体的明确分配，和15的N- NMR化学位移与σ相关段哈米特常数和点电荷。
• 1-Deaza-2'-deoxyadenosine: Phosphonate and Phosphoramidite Building Blocks for Solid-Phase Oligonucleotide Synthesis
  作者：Frank Seela、Thomas Wenzel

  DOI：10.3987/com-92-6214

  日期：——

  The synthesis of the 3'-[(2-cyanoethyl)diisopropylphosphoramidite] (3b) and the 3'-phosphonate (3a) of 1-deaza-2'-deoxyadenosine (1b) is described. For this purpose compound lb was protected at the 6-amino group with a benzoyl residue. Ensuing 4,4'-dimethoxytritylation of lb and phosphitylation afforded the P(III) derivatives(3a) and (3b). They were successfully employed in solid-phase oligodeoxyribonucleotide synthesis of d(c1A-c1A-c1A-A-A-A) (6). C-13-Nmr and N-15-nmr spectra of the compounds (1-5) are discussed.
• Efficient Synthesis of 1-Deaza-6-methoxypurine-N9-<font>β</font>-2′-deoxyribonucleoside and Related DNA Building Blocks
  作者：Dominik A. Megger、Jens Müller

  DOI：10.1080/00397911.2010.505704

  日期：2011.9.1

  An improved synthesis of the 2'-deoxyribonucleoside containing 1-deaza-6-methoxypurine as artificial nucleobase is described. By optimizing the conditions for the deprotection of p-toluoyl-protected 1-deaza-6-nitropurine 2'-deoxyribonucleoside, the isolated yield of the title compound could be increased from 15% to 90%. In addition, the synthesis and characterization of the corresponding 5'-(4,4'-dimethoxytrityl) (DMT) protected phosphoramidite, a potentially useful building block for the synthesis of artificial oligonucleotides, is reported. The title compound offers interesting hydrogen bond donor and metal-binding properties for its application in metal-mediated base pairs.