4-amino-5-(thiazol-2-yl)-7-[2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine | 1252858-36-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 4-amino-5-(thiazol-2-yl)-7-[2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 4-amino-5-(thiazol-2-yl)-7-[2,3,5-tris-O-(tert-butyldimethylsilyl)-β-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine；4-Amino-5-(thiazol-2-yl)-7-[2,3,5-tris-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine；7-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-(1,3-thiazol-2-yl)pyrrolo[2,3-d]pyrimidin-4-amine
• CAS: 1252858-36-8
• 化学式: C₃₂H₅₇N₅O₄SSi₃
• 分子量: 692.158
• InChiKey: URAGPWHGHPTJDQ-UQCYUJMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.84
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-amino-5-(thiazol-2-yl)-7-[2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以85%的产率得到4-amino-7-(β-D-ribofuranosyl)-5-(thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and Significant Cytostatic Activity of 7-Hetaryl-7-deazaadenosines

  摘要：

  A series of 7-aryl- and 7-hetaryl-7-deazaadenosines were prepared by the cross-coupling reactions of unprotected or protected 7-iodo-7-deazaadenosines with (het)arylboronic acids, stannanes, or zinc halides. Nucleosides bearing 5-membered heterocycles at the position 7 exerted potent in vitro antiproliferative effects against a broad panel of hematological and solid tumor cell lines. Cell cycle analysis indicated profound inhibition of RNA synthesis and induction of apoptosis in treated cells. Intracellular conversion to triphosphates has been detected with active compounds. The triphosphate metabolites showed only a weak inhibitory effect on human RNA polymerase II, suggesting potentially other mechanisms for the inhibition of RNA synthesis and quick onset of apoptosis. Initial in vivo evaluation demonstrated an effect of 7-(2-thienyl)-7-deazaadenine ribonucleoside on the survival rate in syngeneic P388D1 mouse leukemia model.

  DOI：

  10.1021/jm2005173
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 4-amino-5-(thiazol-2-yl)-7-[2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and Significant Cytostatic Activity of 7-Hetaryl-7-deazaadenosines

  摘要：

  A series of 7-aryl- and 7-hetaryl-7-deazaadenosines were prepared by the cross-coupling reactions of unprotected or protected 7-iodo-7-deazaadenosines with (het)arylboronic acids, stannanes, or zinc halides. Nucleosides bearing 5-membered heterocycles at the position 7 exerted potent in vitro antiproliferative effects against a broad panel of hematological and solid tumor cell lines. Cell cycle analysis indicated profound inhibition of RNA synthesis and induction of apoptosis in treated cells. Intracellular conversion to triphosphates has been detected with active compounds. The triphosphate metabolites showed only a weak inhibitory effect on human RNA polymerase II, suggesting potentially other mechanisms for the inhibition of RNA synthesis and quick onset of apoptosis. Initial in vivo evaluation demonstrated an effect of 7-(2-thienyl)-7-deazaadenine ribonucleoside on the survival rate in syngeneic P388D1 mouse leukemia model.

  DOI：

  10.1021/jm2005173

文献信息

• 7-deazapurine nucleosides for therapeutic uses
  申请人：Bourderioux Aurelie

  公开号：US09321800B2

  公开（公告）日：2016-04-26

  The invention provides compounds of formula I, wherein R1, R2 and R3 have values defined in the specification and a pharmaceutically acceptable salt thereof; or an optical isomer thereof; or a mixture of optical isomers, as well as compositions comprising such compounds and therapeutic methods that utilize such compounds and/or compositions.

  本发明提供了公式I的化合物，其中R1，R2和R3的值在规范中定义，并且其药学上可接受的盐；或其光学异构体；或光学异构体的混合物，以及包括这些化合物的组合物和利用这些化合物和/或组合物的治疗方法。
• [EN] NOVEL 7-DEAZAPURINE NUCLEOSIDES FOR THERAPEUTIC USES<br/>[FR] NOUVEAUX NUCLÉOSIDES 7-DÉAZAPURINE À DES FINS THÉRAPEUTIQUES
  申请人：ACAD OF SCIENCE CZECH REPUBLIC

  公开号：WO2010121576A3

  公开（公告）日：2011-06-16