(2S,3R,4S,5S)-2-(acetoxymethyl)-5-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-1-yl)tetrahydrofuran-3,4-diyl diacetate | 1374425-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S)-2-(acetoxymethyl)-5-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-1-yl)tetrahydrofuran-3,4-diyl diacetate
• 英文别名: [(2S,3R,4S,5S)-3,4-diacetyloxy-5-(4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 1374425-32-7
• 化学式: C₁₈H₁₈BrN₅O₇
• 分子量: 496.274
• InChiKey: RWUHBIMPCRFQJS-KTMFAHBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  168.65
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S)-2-(acetoxymethyl)-5-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-1-yl)tetrahydrofuran-3,4-diyl diacetate 在 甲醇 、 ammonium hydroxide 、 双氧水 作用下， 反应 8.5h， 生成 4-amino-6-bromo-1-((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)1H-pyrrolo[2,3-d]pyrimidine-5-carboxamide
  参考文献：
  名称：

  CDK-INHIBITING PYRROLOPYRIMIDINONE CARBOXAMIDE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING HEPATOCELLULAR CARCINOMA

  摘要：

  本发明涉及一种CDK抑制吡咯吡嘧啶酮羧酰胺衍生物或其药用可接受的盐，以及含有该衍生物作为活性成分的药物组合物，用于预防或治疗肝细胞癌，本发明的吡咯吡嘧啶酮羧酰胺衍生物组合物通过抑制CDK1和CDK2抑制SNU-354细胞（人类肝癌干细胞）的细胞生长，并通过抑制CDK7和CDK7诱导细胞凋亡，从而可有效用于预防或治疗肝细胞癌。

  公开号：

  US20130237495A1
• 作为产物：
  描述：

  2-氨基-5-溴-1H-吡咯-3,4-二甲腈 在 N,O-双三甲硅基乙酰胺 、 氨 、 水 、 甲烷 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 14.0h， 生成 (2S,3R,4S,5S)-2-(acetoxymethyl)-5-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-1-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  CDK-INHIBITING PYRROLOPYRIMIDINONE CARBOXAMIDE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING HEPATOCELLULAR CARCINOMA

  摘要：

  本发明涉及一种CDK抑制吡咯吡嘧啶酮羧酰胺衍生物或其药用可接受的盐，以及含有该衍生物作为活性成分的药物组合物，用于预防或治疗肝细胞癌，本发明的吡咯吡嘧啶酮羧酰胺衍生物组合物通过抑制CDK1和CDK2抑制SNU-354细胞（人类肝癌干细胞）的细胞生长，并通过抑制CDK7和CDK7诱导细胞凋亡，从而可有效用于预防或治疗肝细胞癌。

  公开号：

  US20130237495A1

文献信息

• Selectivity between N-1 and N-7 nucleosides: regioselective synthesis of BMK-Y101, a potent cdk7 and 9 inhibitor
  作者：Young-Jong Kim、Soon Ho Kwon、Il Hak Bae、B. Moon Kim

  DOI：10.1016/j.tetlet.2013.07.132

  日期：2013.10

  BMK-Y101 is a new pyrrolo[2,3-d]pyrimidine-based potent cdk7 and 9 inhibitor, which is characterized by an intriguing structural feature of N-1 nucleoside, departing from previously reported N-7 nucleoside Cdk inhibitor, xylocydine. Though N-1 nucleosides have appeared in the literature, they have often been considered as kinetic products and thus intermediates of N-7 glycosylation. In the course of the synthetic studies of xylocydine derivatives, we have developed a highly regioselective method to obtain the N-1 nucleoside. The origin of the selectivity is apparently based on the reactivity of the silylated nucleobase and the stability of the resulting N-1 nucleoside. The choice of BSA as a silylating agent was critical in securing the N-1 nucleoside, BMK-Y101. On the other hand, proper selection of reaction conditions promoting transglycosylation provides an efficient route to N-7 nucleosides. (C) 2013 Elsevier Ltd. All rights reserved.
• CDK-INHIBITING PYRROLOPYRIMIDINONE CARBOXAMIDE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING LIVER CELL CANCER
  申请人：SNU R&DB Foundation

  公开号：EP2636677B1

  公开（公告）日：2016-01-13