(2R,3R,4S,5R)-2-(7-amino-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol | 89243-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R)-2-(7-amino-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• 英文别名: 2-chloroadenosine；2-chloroadenosin；(2R,3R,4S,5R)-2-(7-amino-5-chloro-imidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3R,4S,5R)-2-(7-amino-5-chloroimidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 89243-52-7
• 化学式: C₁₁H₁₃ClN₄O₄
• 分子量: 300.702
• InChiKey: NSHIDLDNURVTES-MGUDNFKCSA-N

物化性质

• 沸点：
  693.7±65.0 °C(Predicted)
• 密度：
  2.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：
  127
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R)-2-(7-amino-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol 在 palladium on activated charcoal 氢气 作用下， 生成 3-beta-D-呋喃核糖基-3H-咪唑并[4,5-b]吡啶-7-胺
  参考文献：
  名称：

  Potent and Selective Ligands for Adenosine Binding Sites

  摘要：

  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.

  DOI：

  10.1080/07328319708006189
• 作为产物：
  描述：

  5,7-dichloro-3-(β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine 在 氨 作用下， 生成 (2R,3R,4S,5R)-2-(7-amino-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Potent and Selective Ligands for Adenosine Binding Sites

  摘要：

  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.

  DOI：

  10.1080/07328319708006189

文献信息

• Palladium-Catalyzed Thiomethylation via a Three-Component Cross-Coupling Strategy
  作者：Ming Wang、Zongjun Qiao、Jiaoyan Zhao、Xuefeng Jiang

  DOI：10.1021/acs.orglett.8b02677

  日期：2018.10.5

  this report, the combination of masked inorganic sulfur and dimethyl carbonate was designed to achieve thiomethylated cross coupling of aryl chlorides. Remarkably, this powerful strategy realized thiomethylation of nucleosides bearing unprotected ribose, chloride-containing pharmaceuticals with late-stage coupling, and herbicides possessing multiple heteroatoms and steric hindrance. Moreover, this protocol

  在本报告中，设计了掩蔽的无机硫和碳酸二甲酯的组合，以实现芳基氯的硫代甲基化交叉偶联。值得注意的是，这种强有力的策略实现了带有未保护核糖的核苷的硫代甲基化，具有后期偶联作用的含氯化物的药物以及具有多个杂原子和空间位阻的除草剂。而且，该方案实际上适用于具有较低催化负载和较高产率的多克级合成。
• MODULAR RADIOCHEMISTRY SYNTHESIS SYSTEM
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20150329583A1

  公开（公告）日：2015-11-19

  A modular chemical production system includes multiple modules for performing a chemical reaction, particularly of radiochemical compounds, from a remote location. One embodiment comprises a reaction vessel including a moveable heat source with the position thereof relative to the reaction vessel being controllable from a remote position. Alternatively the heat source may be fixed in location and the reaction vial is moveable into and out of the heat source. The reaction vessel has one or more sealing plugs, the positioning of which in relationship to the reaction vessel is controllable from a remote position. Also the one or more reaction vessel sealing plugs can include one or more conduits there through for delivery of reactants, gases at atmospheric or an elevated pressure, inert gases, drawing a vacuum and removal of reaction end products to and from the reaction vial, the reaction vial with sealing plug in position being operable at elevated pressures. The modular chemical production system is assembled from modules which can each include operating condition sensors and controllers configured for monitoring and controlling the individual modules and the assembled system from a remote position. Other modules include, but are not limited to a Reagent Storage and Delivery Module, a Cartridge Purification Module, a Microwave Reaction Module, an External QC/Analysis/Purification Interface Module, an Aliquotting Module, an F-18 Drying Module, a Concentration Module, a Radiation Counting Module, and a Capillary Reactor Module.

  一个模块化的化学生产系统包括多个模块，用于从远程位置执行化学反应，特别是放射化学化合物的反应。一个实施例包括一个反应容器，其中包括一个可移动的热源，其相对于反应容器的位置可以从远程位置控制。另一种情况是热源可能固定在某个位置，而反应瓶可以移动进入和移出热源。反应容器有一个或多个密封塞，其相对于反应容器的位置可以从远程位置控制。此外，一个或多个反应容器密封塞可以包括一个或多个通道，用于提供反应物、大气或高压气体、惰性气体、抽真空以及将反应产物从反应瓶中移出和移入，带有密封塞的反应瓶在高压下可操作。该模块化化学生产系统由模块组装而成，每个模块可以包括用于监测和控制各个模块和组装系统的操作条件传感器和控制器，可以从远程位置进行监控和控制。其他模块包括但不限于试剂储存和输送模块、柱层净化模块、微波反应模块、外部质控/分析/净化接口模块、等份取样模块、F-18 干燥模块、浓缩模块、辐射计数模块和毛细管反应器模块。
• Purine-Substituted Adenosine Derivatives with Small N⁶-Substituents as Adenosine Receptor Agonists
  作者：A. P. Ijzerman、J. K. von Frijtag Drabbe Künzel、S. Vittori、G. Cristalli

  DOI：10.1080/15257779408013220

  日期：1994.12

  Adenosine, 6-hydroxylaminopurineriboside (HAPR), N6-methyladenosine and various derivatives of which the synthesis is described, were evaluated as adenosine receptor ligands in radioligand binding studies to probe the relative importance for affinity of small N-6-substituents. The findings were incorporated in a recently developed three-dimensional model for the adenosine A, receptor, rationalising the more or less equal contribution to affinity of such different substituents as -OH and -CH3.
• 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.