6-chloro-9-[(2,3-O-isopropylidene)-4-thio-β-D-ribofuranosyl]purine | 900810-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-chloro-9-[(2,3-O-isopropylidene)-4-thio-β-D-ribofuranosyl]purine
• 英文别名: ((3aS,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methanol；[(3aR,4R,6R,6aS)-4-(6-chloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrothieno[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 900810-21-1
• 化学式: C₁₃H₁₅ClN₄O₃S
• 分子量: 342.806
• InChiKey: MZIAEYNEEKDDCI-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-chloro-9-[(2,3-O-isopropylidene)-4-thio-β-D-ribofuranosyl]purine 在 氨 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 2-(6-氨基嘌呤-9-基)-5-(羟基甲基)四氢噻吩-3,4-二醇
  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
• 作为产物：
  描述：

  benzoic acid (3aS,4R,6R,6aR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester 在 甲基碘化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 以62%的产率得到6-chloro-9-[(2,3-O-isopropylidene)-4-thio-β-D-ribofuranosyl]purine
  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

• [EN] CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS<br/>[FR] COMPOSÉS DINUCLÉOTIDIQUES CYCLIQUES UTILISÉS COMME AGONISTES STING
  申请人：MERCK SHARP & DOHME

  公开号：WO2019125974A1

  公开（公告）日：2019-06-27

  A class of polycyclic compounds of general formula (I), wherein Base1, Base2, Y, Za, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, R8a, and R9 are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

  一类具有通用公式（I）的多环化合物的类别，其中Base1，Base2，Y，Za，Xa，Xa1，Xb，Xb1，Xc，Xc1，Xd，Xd1，R1，R1a，R2，R2a，R3，R4，R4a，R5，R6，R6a，R7，R7a，R8，R8a和R9按本说明书中定义，可能对作为I型干扰素产生的诱导剂特别有用，具体作为STING激活剂。还提供了合成和使用化合物的过程。
• CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS
  申请人：MERCK SHARP & DOHME CORP.

  公开号：EP3727401A1

  公开（公告）日：2020-10-28