5-fluoro-4-(1H-imidazol-4-yl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine | 1172127-72-8

• 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: 5-fluoro-4-(1H-imidazol-4-yl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 5-fluoro-4-(1H-imidazol-4-yl)-7-(β-D-ribofuranosyl)-7H-pyrroIo[2,3-d]pyrimidine；(2R,3R,4S,5R)-2-[5-fluoro-4-(1H-imidazol-5-yl)pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1172127-72-8
• 化学式: C₁₄H₁₄FN₅O₄
• 分子量: 335.295
• InChiKey: XCDMTPKQDUFORB-LHNIVKCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-fluoro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-(1-trityl-1H-imidazol-4-yl)-7Hpyrrolo[2,3-d]pyrimidine 在 sodium methylate 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 19.0h， 以70%的产率得到5-fluoro-4-(1H-imidazol-4-yl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  6-(Het)aryl-7-Deazapurine Ribonucleosides as Novel Potent Cytostatic Agents

  摘要：

  A series of novel 7-deazapurine ribonucleosides bearing an alkyl, aryl, or lietaryl group in position 6 and H, F, or Cl atom in position 7 has been prepared either by Pd-catalyzed cross-coupling reactions of the corresponding protected 6-clilot-o-(7-h ilogeiiztted-)7-deiz ipurine ribonucleosides with alkyl- or (het)arylorganometallics followed by deprotection, or by single-step aqueous phase cross-coupling reactions of unprotected 6-chloro-(7-lialogen tted-)7-de iz tl)tii-iiie ri bon ucleos ides with (het)arylboronic acids. Significant cytostatic effect was detected With a Substantial proportion ofthe prepared compounds. The most potent were 7-H or 7-17 derivatives of 6-furyl- or 6-thienyl-7-deazapurines displaying cytostatic activity in multiple cancer cell lines with a geometric mean of 50% growth inhibition concentration ranging from 16 to 96 nM, a potency comparable to or better than that of the nucleoside analogue clofarabinc. lntr icel]Lll ll'pliosphoi-yl itioil to niono- and triphosphates and the inhibition of total RNA synthesis was denionstrated in preliminary study of metabolism and tinechanistin of action Studies.

  DOI：

  10.1021/jm901428k

文献信息

• [EN] NOVEL CYTOSTATIC 7-DEAZAPURINE NUCLEOSIDES<br/>[FR] NOUVEAUX NUCLÉOSIDES 7-DÉAZAPURINE CYTOSTATIQUES
  申请人：ACAD OF SCIENCE CZECH REPUBLIC

  公开号：WO2009089804A1

  公开（公告）日：2009-07-23

  The invention provides compounds of formula (I), wherein R1 and R2 have any of the values defined in the specification and salts thereof, as well as compositions comprising such compounds and therapeutic methods that utilize such compounds.

  这项发明提供了式（I）的化合物，其中R1和R2具有规范中定义的任何值及其盐，以及包含这些化合物的组合物和利用这些化合物的治疗方法。
• NOVEL CYTOSTATIC 7-DEAZAPURINE NUCLEOSIDES
  申请人：INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE ACADEMY OF SCIENCES OF THE CZECH REPUBLIC

  公开号：EP2231689B1

  公开（公告）日：2016-07-20
• US8093226B2
  申请人：——

  公开号：US8093226B2

  公开（公告）日：2012-01-10