5-氨基噻唑并[4,5-D]嘧啶-2(3H)-硫酮 | 892498-86-1

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-氨基噻唑并[4,5-D]嘧啶-2(3H)-硫酮
• 英文名称: 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-thione
• 英文别名: 5-amino-3H-thiazolo[4,5-d]pyrimidine-2-thione；5-Aminothiazolo[4,5-d]pyrimidine-2(3H)-thione；5-amino-3H-[1,3]thiazolo[4,5-d]pyrimidine-2-thione
• CAS: 892498-86-1
• 化学式: C₅H₄N₄S₂
• 分子量: 184.246
• InChiKey: CPJXYEPRMYVJJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-氨基噻唑并[4,5-D]嘧啶-2(3H)-硫酮 在 双氧水 、 N,N-二(三甲基硅基)乙酰胺 、 sodium hydroxide 作用下， 以 aq. phosphate buffer 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 20.0~80.0 ℃ 、15.0 kPa 条件下， 反应 18.5h， 生成 (2R,3R,4R,5R)-2-(hydroxymethyl)-5-(5-amino-2-oxothiazolo[4,5-d]pyrimidin-3(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  Development of a Robust and Sustainable Process for Nucleoside Formation

  摘要：

  A practical and robust process for the synthesis of an Isatoribine pro-drug was demonstrated. The process relies on a streamlined glycosylation carried out in xylene and an effective regioselective enzymatic hydrolysis that can be run in a semicontinuous way. Analysis of the process mass intensity established the high impact from an environmental standpoint of our process improvement.

  DOI：

  10.1021/op300335d
• 作为产物：
  描述：

  potassium ethyl xanthogenate 、 5-溴嘧啶-2,4-二胺 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 13.0h， 以87%的产率得到5-氨基噻唑并[4,5-D]嘧啶-2(3H)-硫酮
  参考文献：
  名称：

  Novel process for the preparation of 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-one

  摘要：

  本发明涉及制备标题化合物5-氨基-3H-噻唑并[4,5-d]嘧啶-2-酮的方法，该化合物是制备某些噻唑并[4,5-d]嘧啶核苷的有用中间体，这些核苷可以作为免疫调节剂有用。

  公开号：

  US20070117979A1

文献信息

• 3,5-DISUBSTITUTED AND 3,5,7-TRISUBSTITUTED-3H-OXAZOLO AND 3H-THIAZOLO[4,5-d]PYRIMIDIN-2-ONE COMPOUNDS AND PRODRUGS THEREOF
  申请人：Webber Stephen E.

  公开号：US20110275589A1

  公开（公告）日：2011-11-10

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑并[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用此类化合物及其前药的治疗或预防用途，以及含有它们的制药组合物和通过给予这些化合物和前药的有效量来治疗本文所述疾病和疾病的方法。
• 3,5-Disubsitituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof
  申请人：Anadys Pharmaceuticals, Inc.

  公开号：US07560544B2

  公开（公告）日：2009-07-14

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代的3H-噁唑和3H-噻唑[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用这些化合物及其前药的治疗或预防用途，以及含有它们的制药组合物，以及通过给予这些化合物和前药的有效量来治疗所述疾病和障碍的方法。
• Process for the preparation of 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-one
  申请人：Anadys Pharmaceuticals, Inc.

  公开号：US07781581B2

  公开（公告）日：2010-08-24

  The present invention relates to a process for the preparation of 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-one which is a useful intermediate in the preparation of certain thiazolo[4,5-d]pyrimidine nucleosides. The process comprises halogenating 2,4-diaminopyrimidine to form 2,4-diamino-5-halo-pyrimidine and then cyclocondensing the 2,4-diamino-5-halo-pyrimidine to form 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-thione. The 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-thione is then oxidized to afford the 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-one.

  本发明涉及一种制备5-氨基-3H-噻唑[4,5-d]嘧啶-2-酮的方法，该方法是制备某些噻唑[4,5-d]嘧啶核苷的有用中间体。该方法包括卤代2,4-二氨基嘧啶以形成2,4-二氨基-5-卤代嘧啶，然后环合2,4-二氨基-5-卤代嘧啶以形成5-氨基-3H-噻唑[4,5-d]嘧啶-2-硫醚。然后将5-氨基-3H-噻唑[4,5-d]嘧啶-2-硫醚氧化以得到5-氨基-3H-噻唑[4,5-d]嘧啶-2-酮。
• 3,5-Disubstituted and 3,5,7-Trisubstituted-3H-Oxazolo and 3H-Thiazolo[4,5-d]pyrimidin-2-one Compounds and Prodrugs Thereof
  申请人：Webber Stephen E.

  公开号：US20130259831A1

  公开（公告）日：2013-10-03

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  该发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑并[4,5-d]嘧啶-2-酮化合物及其前药。该发明还涉及使用这些化合物的治疗或预防用途，以及含有它们的制药组合物，以及通过给予这些化合物和前药的有效量来治疗本文所述的疾病和障碍的方法。
• 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof
  申请人：Webber Stephen E.

  公开号：US08883758B2

  公开（公告）日：2014-11-11

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑并[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用此类化合物和制药组合物的治疗或预防用途，并通过给予有效量的此类化合物和前药来治疗本文所述的疾病和障碍的方法。