5-amino-3-(2-C-methyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2,7(3H,6H)-dione | 892499-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-amino-3-(2-C-methyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2,7(3H,6H)-dione
• 英文别名: 5-amino-3-(2'-C-methyl-β-D-ribofuranosyl)-3H,6Hthiazolo[4,5-d]pyrimidine-2,7-dione；5-Amino-3-(2'-C-methyl-beta-D-ribofuranosyl)-3H,6H-thiazolo[4,5-d]pyrimidine-2,7-dione；5-amino-3-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione
• CAS: 892499-46-6
• 化学式: C₁₁H₁₄N₄O₆S
• 分子量: 330.321
• InChiKey: OHFFYWAZFMJHAV-PKQJPSSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  183
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-amino-3-(2,3,5-tri-O-benzoyl-2-C-methyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2,7(3H,6H)-dione 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以71%的产率得到5-amino-3-(2-C-methyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2,7(3H,6H)-dione
  参考文献：
  名称：

  7-Halogenated 7-deazapurine 2′-C-methylribonucleosides

  摘要：

  通过“一锅法”糖基化协议（Vorbrüggen糖基化），合成了与腺苷、肌苷和鸟苷相关的卤代7-脱氮嘌呤2'-C-甲基核糖核苷。免疫核苷2'-C-甲基核糖核苷4也通过相同的糖基化策略制备。通过这种途径，抗HCV活性化合物7-氟-7-脱氮-2'-C-甲基腺苷（1b）的合成得到明显简化，同时其他核苷首次合成。对7-氟-7-脱氮-2'-C-甲基肌苷（2b）进行了单晶X射线分析，结果显示糖基键采取反式取向（χ = -139.9(2)°），而糖部分呈N构象（C3'-内环；P = 4.3(1)°，τm = 42.4(1)°）。

  DOI：

  10.1135/cccc2011124

文献信息

• 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：Webber E. Stephen

  公开号：US20060160830A1

  公开（公告）日：2006-07-20

  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-噁唑啉和3H-噻唑啉[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和前药的治疗或预防用途，以及包含它们的制药组合物，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。
• 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-disubstituted 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：US08097718B2

  公开（公告）日：2012-01-17

  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。本发明还涉及使用这些化合物和制药组合物的治疗或预防用途，并通过给予这些化合物和前药的有效量来治疗本说明书中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：US20120121541A1

  公开（公告）日：2012-05-17

  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和前药的治疗或预防用途，以及含有它们的制药组合物，并通过给予这些化合物和前药的有效剂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：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。