2-Chloro-4'-thioadenosine | 158814-07-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2-Chloro-4'-thioadenosine
• 英文别名: 2-chloro-4'-thioadenine；(2R,3R,4S,5R)-2-(6-amino-2-chloropurin-9-yl)-5-(hydroxymethyl)thiolane-3,4-diol
• CAS: 158814-07-4
• 化学式: C₁₀H₁₂ClN₅O₃S
• 分子量: 317.756
• InChiKey: PPLPBEAPQUBYJP-UUOKFMHZSA-N

物化性质

• 熔点：
  220-222 °C
• 沸点：
  582.6±60.0 °C(Predicted)
• 密度：
  2.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  156
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-Chloro-4'-thioadenosine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.05h， 生成 2-chloro-2'-deoxy-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine
  参考文献：
  名称：

  Synthesis and Biological Activity of 4′-Thionucleosides of 2-Chloroadenine¹

  摘要：

  1,2,3,5-Tetra-O-acetyl-4-thio-D-ribofuranose,prepared from 2,3,5-tri-O-benzyl-D-ribofuranose in four steps, was converted to the corresponding 2-chloroadenine nucleoside (8), which was deoxygenated to obtain 2-chloro-2'-deoxy-4'-thioadenosine (12). This is the first report of a 2'-deoxy-4'-thioribonucleoside of a purine rather than a pyrimidine. These novel nucleosides (8 and 12) were cytotoxic to several human tumor cell lines in culture.

  DOI：

  10.1080/15257779408009484
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 甲基碘化镁 、 三甲基硅基甲烷磺酸酯 、 氨 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 112.0h， 生成 2-Chloro-4'-thioadenosine
  参考文献：
  名称：

  Design, synthesis, and biological activity of N6-substituted-4′-thioadenosines at the human A3 adenosine receptor

  摘要：

  A large series of N-6-substituted-4'-thioadenosines were synthesized starting from D-gulonic-gamma-Iactone, and structure-activity relationships were studied at the human A(3) and other subtypes of adenosine receptors (ARs). 2-Chloro-substituted and 2-H analogues were compared. 2-Chloro-N-6-methyl-4'-thioadeno sine 19b was a highly potent and selective agonist (K-i = 0.8 +/- 0.1 nM in binding) at the A(3)AR, and displayed the same relative efficacy in receptor activation as a known full agonist, Cl-IB-MECA. Most of N6-substituted-4'-thioadenosines were less potent in binding than the corresponding N-6-substituted-adenosines or N-6-substituted-4'thioadenosine-5'-uronamides. N-6-(3-lodobenzyl) derivative 19g was demonstrated to be an A(3)AR-selective partial agonist displaying a Ki value of 3.2 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.030

文献信息

• The Synthesis and Biological Activity of Certain 4'-Thionucleosides
  作者：John Secrist、William Parker、Kamal Tiwari、Lea Messini、Sue Shaddix、Lucy Rose、L. Lee Bennett、John Montgomery

  DOI：10.1080/15257779508012449

  日期：1995.5.1

  Abstract Results are presented on the synthesis and biological activity of several types of 4′-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4′-thiothymidine are also presented.

  摘要介绍了几种类型的4'-硫代核苷作为潜在抗癌剂的合成和生物学活性。还介绍了有关4'-硫代胸苷的作用机理的详细研究。
• D-4′-THIOADENOSINE DERIVATIVES AS HIGHLY POTENT AND SELECTIVE AGONISTS AT THE HUMAN A₃ ADENOSINE RECEPTOR
  作者：Hyouk Woo Lee、Dae Hong Shin、Ji Young Jung、Hea Ok Kim、Moon Woo Chun、N. Melman、Z.-G. Gao、Kenneth A. Jacobson、Lak Shin Jeong

  DOI：10.1081/ncn-200061827

  日期：2005.4.1

  4'-Thionucleoside derivatives as potent and selective A(3) adenosine receptor agonists were synthesized, starting from D-gulono-gamma-lactone via D-thioribosyl acetate as a key intermediate, among which the 2-chloro-N-6-methyladenosine-5'-methyluronamide showed the most potent and selective binding affinity (K-i = 0.28 +/- 0.09 nM) at the human A(3) adenosine receptor.
• US7199127B2
  申请人：——

  公开号：US7199127B2

  公开（公告）日：2007-04-03
• [EN] COMPOSITIONS AND METHODS USING ADENOSINE A3 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY EYE DISEASES<br/>[FR] COMPOSITIONS ET PROCÉDÉS UTILISANT DES ANTAGONISTES DU RÉCEPTEUR DE L'ADÉNOSINE A3 POUR TRAITEMENT DE MALADIES OCULAIRES INFLAMMATOIRES
  申请人：ACORN BIOMEDICAL INC

  公开号：WO2012125400A1

  公开（公告）日：2012-09-20

  Disclosed are compositions comprising adenosine A3 receptor antagonists and methods of their use for the treatment of inflammatory eye diseases, such as uveitis and dry eye.
• Design, synthesis, and biological activity of N6-substituted-4′-thioadenosines at the human A3 adenosine receptor
  作者：Lak Shin Jeong、Hyuk Woo Lee、Hea Ok Kim、Ji Young Jung、Zhan-Guo Gao、Heng T. Duong、Srikar Rao、Kenneth A. Jacobson、Dae Hong Shin、Jeong A Lee

  DOI：10.1016/j.bmc.2006.03.030

  日期：2006.7.15

  A large series of N-6-substituted-4'-thioadenosines were synthesized starting from D-gulonic-gamma-Iactone, and structure-activity relationships were studied at the human A(3) and other subtypes of adenosine receptors (ARs). 2-Chloro-substituted and 2-H analogues were compared. 2-Chloro-N-6-methyl-4'-thioadeno sine 19b was a highly potent and selective agonist (K-i = 0.8 +/- 0.1 nM in binding) at the A(3)AR, and displayed the same relative efficacy in receptor activation as a known full agonist, Cl-IB-MECA. Most of N6-substituted-4'-thioadenosines were less potent in binding than the corresponding N-6-substituted-adenosines or N-6-substituted-4'thioadenosine-5'-uronamides. N-6-(3-lodobenzyl) derivative 19g was demonstrated to be an A(3)AR-selective partial agonist displaying a Ki value of 3.2 nM. (c) 2006 Elsevier Ltd. All rights reserved.