3-<2-deoxy-β-D-erythro-pentofuranosyl>-3H-imidazo<4,5-b>pyridine | 125178-07-6

• 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>-3H-imidazo<4,5-b>pyridine
• 英文别名: 3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo<4,5-b>pyridine；9-(2-deoxy-β-D-ribofuranosyl)-1-deazapurine；1-deazapurine β-2'-deoxyribonucleozide；3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[4,5-b]pyridine；(2R,3S,5R)-2-(hydroxymethyl)-5-imidazo[4,5-b]pyridin-3-yloxolan-3-ol
• CAS: 125178-07-6
• 化学式: C₁₁H₁₃N₃O₃
• 分子量: 235.243
• InChiKey: CFUZUDJNRCIKSC-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 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：
  80.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<2-deoxy-β-D-erythro-pentofuranosyl>-3H-imidazo<4,5-b>pyridine 在 recombinant Drosophila melanogaster kinase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 various solvent(s) 为溶剂， 生成 Phosphoric acid mono-((2R,3S,5R)-3-hydroxy-5-imidazo[4,5-b]pyridin-3-yl-tetrahydro-furan-2-ylmethyl) ester
  参考文献：
  名称：

  非天然核苷的酶促磷酸化

  摘要：

  为了扩大遗传字母表，已经开发了许多非天然的、主要是疏水性的核苷类似物，它们在双链 DNA 中和酶促合成过程中选择性地配对。在含有这些碱基对的 DNA 的体外有效复制方面取得了重大进展。然而，基因字母表的体内扩展将要求非天然三磷酸核苷在细胞内以足够的浓度用于 DNA 复制。我们报告了我们为开发基于核苷补救酶的非自然体内核苷磷酸化途径所做的初步努力。该途径的第一步由黑腹果蝇核苷激酶催化，该激酶催化核苷磷酸化为相应的单磷酸酯。

  DOI：

  10.1021/ja028050m
• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 氢氧化钾 、 三(3,6-二氧杂庚基)胺 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 36.33h， 生成 3-<2-deoxy-β-D-erythro-pentofuranosyl>-3H-imidazo<4,5-b>pyridine
  参考文献：
  名称：

  6-取代的1-脱氮嘌呤2'-脱氧核糖核苷的合成

  摘要：

  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。

  DOI：

  10.1002/hlca.19960790117

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。
• Imidazopyridine Derivatives
  申请人：Hirao Ichiro

  公开号：US20080125381A1

  公开（公告）日：2008-05-29

  The present invention relates to a novel imidazo[4,5-b]pyridine derivative compound represented by Formula (I) and a pharmaceutically acceptable salt thereof. The present invention also relates to a method for preparing the above compound. The present invention further relates to a pharmaceutical composition comprising the above compound. The above compound has growth inhibitory activity on cancer cells, and this effect is dissociated from growth inhibitory activity on normal cells. This indicates that the compound is useful as a novel anticancer agent.

  本发明涉及一种新型咪唑并[4,5-b]吡啶衍生物化合物，其表示为公式（I），以及其药学上可接受的盐。本发明还涉及制备上述化合物的方法。本发明还涉及包含上述化合物的制药组合物。上述化合物具有对癌细胞的生长抑制活性，且该效果与对正常细胞的生长抑制活性分离。这表明该化合物可用作新型抗癌剂。
• IMIDAZOPYRIDINE DERIVATIVE
  申请人：Riken

  公开号：EP1847546B1

  公开（公告）日：2012-11-28
• [Hg(9-methyl-1-deazapurine)2](NO3)2·H2O: a complex with a distorted hexagonal bipyramidal metal ion coordination sphere
  作者：Jens Müller、Fabian-Alexander Polonius、Michael Roitzsch

  DOI：10.1016/j.ica.2004.11.038

  日期：2005.3

  Reaction of 9-methyl-1-deazapurine (9-MeDP) with Hg(CF3COO)(2) in the presence of NaNO3 yields the title compound [Hg(9-MeDP)(2)](NO3)(2) center dot H2O with the two 9-MeDP ligands bound to the metal ion via their N7 positions. The X-ray structure is reported: monoclinic, P2(1)/c (no. 14), a = 5.4015(11), b = 20.467(4), c = 17.775(4) angstrom, beta = 97.00(3)degrees, V = 1950.4(7) angstrom(-3), Z = 4. Hg is eight-coordinate with two trans-oriented Hg-N bonds (2.073(3) and 2.075(3) angstrom) and three nearly coplanar, bidentate nitrate moieties (Hg-O: 2.716(3)-2.985(4) angstrom), leading to a distorted hexagonal bipyramidal environment of the metal ion. Within this structure, the nitrate ions form a honeycomb-like chain structure with Hg-II being positioned inside the combs. This work represents the first report of such geometry for a transition metal ion surrounded by symmetrically bidentate nitrate ions. The corresponding nucleoside, 1-deazapurine 2'-deoxyribonucleoside, also forms a stable 2:1 complex with Hg-II as was shown by H-1 NMR spectroscopy, making it a potential candidate for incorporation into nucleic acids based on metal-mediated base pairs. (c) 2004 Elsevier B.V. All rights reserved.
• Efforts toward Expansion of the Genetic Alphabet:  Optimization of Interbase Hydrophobic Interactions
  作者：Yiqin Wu、Anthony K. Ogawa、Markus Berger、Dustin L. McMinn、Peter G. Schultz、Floyd E. Romesberg

  DOI：10.1021/ja0009931

  日期：2000.8.1

  Six novel unnatural nucleobases have been characterized that form stable base pairs in duplex DNA, relying nor on hydrogen bonds, but rather on interbase hydrophobic interactions. These nucleobases are derivatives of the hydrophobic base pair between 7-azaindole (7AI) and isocarbostyril (ICS). Derivatives of 7AI and ICS were examined that have increased hydrophobic surface area, as well as increased polarizability. As observed with 7AI and ICS, these derivatives are recognized as substrates by Klenow fragment of Escherichia coli DNA polymerase I. The unnatural base pair between pyrrolopyrizine (PP) and C3-methylisocarbostyril (MICS) is enzymatically incorporated into DNA with high efficiency (k(cat)/K-M = 10(6) M-1 min(-1)) and moderate selectivity. These studies represent a significant step toward the generation of astable, orthogonal base pair that can be enzymatically incorporated into DNA with good fidelity.