4-amino-5-iodo-2-methyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine | 1536110-28-7

• 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-iodo-2-methyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: (2R,3R,4S,5R)-2-(4-amino-5-iodo-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3R,4S,5R)-2-(4-amino-5-iodo-2-methylpyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1536110-28-7
• 化学式: C₁₂H₁₅IN₄O₄
• 分子量: 406.18
• InChiKey: SHBDPJFAMJHMOF-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  21
• 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：
  127
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-amino-5-iodo-2-methyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以97%的产率得到2-methyltubercidin
  参考文献：
  名称：

  Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6-Substituted 7-(Het)aryl-7-deazapurine Ribonucleosides

  摘要：

  A series of 80 7-(het)aryl- and 7-ethyny1-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were prepared, and the biological activity of the compounds was studied and compared with that of the parent 7-(het)ary1-7-deazaadenosine series. Several of the compounds, in particular 6-substituted 7-deazapurine derivatives bearing a furyl or ethynyl group at position 7, were significantly cytotoxic at low nanomolar concentrations whereas most were much less potent or inactive. Promising activity was observed with some compounds against Mycobacterium bovis and also against hepatitis C virus in a replicon assay.

  DOI：

  10.1021/jm4018948
• 作为产物：
  描述：

  4-chloro-5-iodo-2-methyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以92%的产率得到4-amino-5-iodo-2-methyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6-Substituted 7-(Het)aryl-7-deazapurine Ribonucleosides

  摘要：

  A series of 80 7-(het)aryl- and 7-ethyny1-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were prepared, and the biological activity of the compounds was studied and compared with that of the parent 7-(het)ary1-7-deazaadenosine series. Several of the compounds, in particular 6-substituted 7-deazapurine derivatives bearing a furyl or ethynyl group at position 7, were significantly cytotoxic at low nanomolar concentrations whereas most were much less potent or inactive. Promising activity was observed with some compounds against Mycobacterium bovis and also against hepatitis C virus in a replicon assay.

  DOI：

  10.1021/jm4018948

文献信息

• [EN] PYRROLOPYRIMIDINE NUCLEOSIDES AND ANALOGS THEREOF USEFUL AS ANTIVIRAL AGENTS<br/>[FR] NUCLÉOSIDES DE PYRROLOPYRIMIDINE ET ANALOGUES DE CEUX-CI UTILES EN TANT QU'AGENTS ANTIVIRAUX
  申请人：CHIMERIX INC

  公开号：WO2017024310A1

  公开（公告）日：2017-02-09

  The present disclosure provides pyrrolopyrimidine nucleoside analogs of the Formula I, Formula IA, Formula IB, or Formula II and phospholipid conjugates and pharmaceutical compositions thereof wherein Rc and A are defined herein. Also presented are methods of treating and/or preventing viral infection and/or viral infection-associated disease or disorder with one or more compounds of Formula I, Formula IA, Formula IB, or Formula II.

  本公开提供式I、式IA、式IB或式II的吡咯嘧啶嘧啶核苷类似物以及磷脂共轭物和制药组合物，其中Rc和A的定义如本文所述。还提供使用一种或多种式I、式IA、式IB或式II的化合物治疗和/或预防病毒感染和/或与病毒感染相关的疾病或障碍的方法。
• Pyrrolopyrimidine nucleosides and analogs thereof
  申请人：Chimerix, Inc.

  公开号：US10407457B2

  公开（公告）日：2019-09-10

  The present disclosure provides pyrrolopyrimidine nucleoside analogs of the Formula I, Formula IA, Formula IB, or Formula II and phospholipid conjugates and pharmaceutical compositions thereof wherein Rc and A are defined herein. Also presented are methods of treating and/or preventing viral infection and/or viral infection-associated disease or disorder with one or more compounds of Formula I, Formula IA, Formula IB, or Formula II.

  本公开提供了式I、式IA、式IB或式II的吡咯并嘧啶核苷类似物及其磷脂共轭物和药物组合物，其中Rc和A在本文中定义。还提出了用一种或多种式I、式IA、式IB或式II化合物治疗和/或预防病毒感染和/或病毒感染相关疾病或紊乱的方法。
• PYRROLOPYRIMIDINE NUCLEOSIDES AND ANALOGS THEREOF
  申请人：Chimerix, Inc.

  公开号：US20170044202A1

  公开（公告）日：2017-02-16

  The present disclosure provides pyrrolopyrimidine nucleoside analogs of the Formula I, Formula IA, Formula IB, or Formula II and phospholipid conjugates and pharmaceutical compositions thereof wherein It c and A are defined herein. Also presented are methods of treating and/or preventing viral infection and/or viral infection-associated disease or disorder with one or more compounds of Formula I, Formula IA, Formula IB, or Formula II.
• US9701706B2
  申请人：——

  公开号：US9701706B2

  公开（公告）日：2017-07-11
• US9708359B2
  申请人：——

  公开号：US9708359B2

  公开（公告）日：2017-07-18