5,7-dichloro-3-(β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine | 56707-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,7-dichloro-3-(β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
• 英文别名: 1-(5,7-dichloro-imidazo[4,5-b]pyridin-3-yl)-β-D-1-deoxy-ribofuranose；5,7-Dichloro-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine；(2R,3R,4S,5R)-2-(5,7-dichloroimidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 56707-85-8
• 化学式: C₁₁H₁₁Cl₂N₃O₄
• 分子量: 320.132
• InChiKey: XEPZHPUOYCNEDI-MGUDNFKCSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  598.2±60.0 °C(Predicted)
• 密度：
  1.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  101
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,7-dichloro-3-(β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 135.0 ℃ 、344.73 kPa 条件下， 反应 53.0h， 生成 N6-<(R)-(-)-1-methyl2-phenethyl>-1-deazaadenosine
  参考文献：
  名称：

  腺苷受体激动剂：腺苷衍生物的1-deaza类似物的合成和生物学评估。

  摘要：

  为了寻找更具选择性的A1腺苷受体激动剂，N6-[（R）-（-）-1-甲基-2-苯乙基] -1-脱氮杂腺苷（1-deaza-R-PIA，3a），N6-环戊基-从5,7-二氯-3-β-D合成了1-deazaadenosine（1-deazaCPA，3b），N6-cyclohexyl-1-deazaadenosine（1-deazaCHA，3c）和相应的2-氯衍生物2a-c。 -核呋喃糖基-3H-咪唑并[4,5-b]吡啶。另一方面，制备了N-乙基-1′-脱氧-1′-（1-deaza-6-氨基-9H-嘌呤-9-基）-β-D-呋喃呋喃核糖酰胺（1-deazaNECA，10）。为了寻找更具选择性的A2激动剂，从7-硝基-3-β-D-呋喃呋喃糖基-3H-咪唑并[4,5-b]吡啶中合成了吡咯烷酮。在腺苷酸环化酶和放射性配体结合研究中已经确定了所有deaza类似物对腺苷受体的活性。1-DeazaNECA被证

  DOI：

  10.1021/jm00401a018
• 作为产物：
  描述：

  4-hydroxyimidazo[4,5-b]pyridine 在 氨 、 硝酸 、 四氯化锡 、 三氟乙酸 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.17h， 生成 5,7-dichloro-3-(β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  发荧光的同功能核糖核苷：评估腺苷脱氨酶活性和抑制作用。

  摘要：

  异噻唑并[4,3-d]嘧啶基腺苷（tz A）和2-氨基腺苷（tz 2-AA）类似物的酶促转化为相应的异噻唑并[4,3-d]嘧啶基肌苷（tz I）评估了鸟苷（tz G）衍生物，并将其与天然腺苷转化为肌苷的转化率进行了比较。Henri-Michaelis-Menten分析为高通量筛选测定提供了基础，并且在已知和新合成的抑制剂存在下，通过基于荧光的tz A转化为tz I的荧光分析显示了该测定的有效性。

  DOI：

  10.1002/cbic.201800665

文献信息

• F-substituted-3-.beta.-D-ribofuranosyl-3H-imidazo[4,5-b]pyridines and
  申请人：Burroughs Wellcome Co.

  公开号：US04780452A1

  公开（公告）日：1988-10-25

  This invention discloses a group of compounds of formula (I) ##STR1## wherein R.sup.1 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, COOR.sup.4 (R.sup.4 is H or C.sub.1-4 alkyl) or trifluoromethyl; R.sup.2, R.sup.5 and R.sup.6 are the same or different and can be hydrogen, hydroxy, OCOR.sup.7 (wherein R.sup.7 is hydrogen, C.sub.1-4 alkyl, phenyl optionally substituted) or halo; and R.sup.3 is hydrogen, COR.sup.4, C.sub.3-6 cycloalkyl or C.sub.1-4 alkyl or alkenyl; R.sup.2 may also be a phosphate group and pharmaceutically acceptable salts thereof which have been found to have analgesic activity. In addition, these compounds have antiinflammatory, antipyretic, antihypertensive and vasodilatory activity in varying degrees. Some of these compounds also have antiprotozoal and antiviral properties.

  本发明公开了一组化合物，其化学式为（I）其中R.sup.1为氢、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、COOR.sup.4（R.sup.4为H或C.sub.1-4烷基）或三氟甲基；R.sup.2、R.sup.5和R.sup.6相同或不同，可以是氢、羟基、OCOR.sup.7（其中R.sup.7为氢、C.sub.1-4烷基、苯基可选择取代）或卤素；而R.sup.3为氢、COR.sup.4、C.sub.3-6环烷基或C.sub.1-4烷基或烯基；R.sup.2也可以是磷酸酯基及其药学上可接受的盐，发现具有镇痛活性。此外，这些化合物在不同程度上具有抗炎、退烧、降压和扩血管活性。其中一些化合物还具有抗原虫和抗病毒性能。
• Nucleoside Analogues
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0260852A2

  公开（公告）日：1988-03-23

  This invention discloses a group of compounds of formula (I) wherein R¹ is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy COOR⁴ (R⁴ is H or C1-4 alkyl) or trifluoromethyl; R², R⁵ and R⁶ are the same or different and can be hydrogen, hydroxy, OCOR⁷ (wherein R⁷ is hydrogen, C1-4 alkyl, phenyl optionally substituted) or halo; and R³ is hydrogen, COR⁴, C3-6 cycloalkyl or C1-4 alkyl or alkenyl; R² may also be a phosphate group and pharmaceu­tically acceptable salts thereof which have been found to have analgesic activity. In addition, these compounds have antiinflammatory, antipyretic, antihypertensive and vasodilatory activity in varying degrees. Some of these compounds also have antiprotozoal and antiviral properties.

  本发明公开了一组式 (I) 的化合物 其中 R¹ 是氢、卤素、C1-4 烷基、C1-4 烷氧基 COOR⁴（R⁴ 是 H 或 C1-4 烷基）或三氟甲基；R²、R⁵ 和 R⁶ 可以相同或不同，可以是氢、羟基、OCOR⁷（其中 R⁷ 是氢、C1-4 烷基、任选取代的苯基）或卤素；和 R³ 是氢、COR⁴、C3-6 环烷基或 C1-4 烷基或烯基；R² 也可以是磷酸基团及其药学上可接受的盐类，它们已被发现具有镇痛活性。此外，这些化合物还具有不同程度的抗炎、解热、降血压和血管扩张活性。其中一些化合物还具有抗原虫和抗病毒特性。
• <i>N</i>-Cycloalkyl Derivatives of Adenosine and 1-Deazaadenosine as Agonists and Partial Agonists of the A₁ Adenosine Receptor
  作者：Sauro Vittori、Anna Lorenzen、Christina Stannek、Stefano Costanzi、Rosaria Volpini、Adriaan P. IJzerman、Jakobien K. Von Frijtag Drabbe Kunzel、Gloria Cristalli

  DOI：10.1021/jm9911231

  日期：2000.1.1

  A number of cycloalkyl substituents (from C-3 to C-8) have been int-reduced on the 6-amino group of adenosine, 1-deazaadenosine, and 2'-deoxyadenosine, bearing or not a chlorine atom at the 2-position, to evaluate the influence on the A(1) and A(2A) affinity of steric hindrance and lipophilicity. Furthermore, the guanosine 5'-triphosphate (GTP) shift and the maximal induction of guanosine 5'-(gamma-thio)triphosphate ([S-35]GTP gamma S) binding to G proteins in rat brain membranes were used to determine the intrinsic activity of these nucleosides at the A(1) adenosine receptor. All compounds of the ribose-bearing series proved to be full agonists, the 1-deaza derivatives showing affinities for the Al receptor about 10-fold lower than the corresponding adenosines. On the other hand, all the 2'-deoxyribose derivatives bind to the A(1) receptor with affinities in the high nanomolar range, with the 2-chloro substituted compounds showing slightly higher affinities than the 2-unsubstituted counterparts. In terms of the potencies, the most potent compounds proved to be those bearing four- and five-membered rings. Both GTP shifts and [S-35]-GTP gamma S experiments showed that most of the 2'-deoxyadenosine derivatives are partial agonists, The 2'-deoxyadenosine derivatives which were identified as partial agonists consistently detected fewer Az receptors in the high-affinity state than full agonists. However, it is worthwhile noting that there was not a simple Linear relationship between receptor occupancy and activation. These results indicate that a critical density of A(1) adenosine receptors in the high-affinity state is required for G protein activation.
• Potent and Selective Ligands for Adenosine Binding Sites
  作者：G. Cristalli、E. Camaioni、E. Di Francesco、A. Eleuteri、S. Vittori、R. Volpini

  DOI：10.1080/07328319708006189

  日期：1997.7

  A number of selective ligands for the different binding sites of adenosine have been synthesized and tested in several pharmacological models. The aim of these synthetic efforts is both to improve the knowledge of structure-activity relationships in the adenosine-related biological systems and to develop drugs from some of these molecules.
• KRENITSKY, THOMAS A.;RIDEOUT, JANET L.;KOSZALKA, GEORGE W.
  作者：KRENITSKY, THOMAS A.、RIDEOUT, JANET L.、KOSZALKA, GEORGE W.

  DOI：——

  日期：——