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 | 1314096-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 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；4-amino-6-bromo-5-cyano-1-(β-L-xylofuranosyl)-pyrrolo[2,3-d]pyrimidine；BMK-Y101；4-amino-6-bromo-1-[(2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide
• CAS: 1314096-69-9
• 化学式: C₁₂H₁₄BrN₅O₅
• 分子量: 388.178
• InChiKey: QVFBAVHEHBUGMY-YJMZUNRSSA-N

物化性质

• 沸点：
  560.3±60.0 °C(Predicted)
• 密度：
  2.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  169.74
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  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 在 吡啶 作用下， 以 吡啶 为溶剂， 反应 13.0h， 生成 (2S,3R,4S,5S)-2-(4-amino-6-bromo-5-carbamoyl-1H-pyrrolo[2,3-d]pyrimidin-1-yl)-5-(isobutyryloxy methyl)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
• 作为产物：
  描述：

  在 双氧水 作用下， 反应 8.0h， 以1.421 g的产率得到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

文献信息

• CDK-inhibiting pyrrolopyrimidine carboxamide derivative or pharmaceutically acceptable salt thereof, and pharmaceutical composition containing the same as active ingredient for preventing or treating hepatocellular carcinoma
  申请人：Lee Seung Ki

  公开号：US09062088B2

  公开（公告）日：2015-06-23

  The present invention relates to a CDK-inhibiting pyrrolopyrimidine carboxamide derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same as an active ingredient for preventing or treating liver cell cancer. Compositions comprising a pyrrolopyrimidine carboxamide derivative of the present invention suppress the cell growth of SNU-354 cell, which is a liver cancer stem cell in humans, by inhibiting CDK1 and CDK2, and induces cell apoptosis of the cell by inhibiting CDK7 and CDK 7. Such compositions are useful for preventing or treating liver cell cancer.

  本发明涉及一种CDK抑制剂吡咯吡嘧啶羧酰胺衍生物或其药学上可接受的盐，以及包含其作为活性成分的制药组合物，用于预防或治疗肝细胞癌。本发明的吡咯吡嘧啶羧酰胺衍生物组合物通过抑制CDK1和CDK2抑制SNU-354人类肝癌干细胞的细胞生长，并通过抑制CDK7和CDK 7诱导细胞凋亡。这样的组合物对于预防或治疗肝细胞癌非常有用。
• 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
• US9062088B2
  申请人：——

  公开号：US9062088B2

  公开（公告）日：2015-06-23
• [EN] 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<br/>[FR] DÉRIVÉ DE CARBOXAMIDE DE PYRROLOPYRIMIDINONE INHIBANT LES CDK OU SEL PHARMACEUTIQUEMENT ACCEPTABLE DE CELUI-CI, ET COMPOSITION PHARMACEUTIQUE CONTENANT CE DÉRIVÉ COMME PRINCIPE ACTIF ET DESTINÉE À PRÉVENIR OU À TRAITER UN CARCINOME HÉPATOCELLULAIRE
  申请人：SNU R&DB FOUNDATION

  公开号：WO2012060482A1

  公开（公告）日：2012-05-10

  본 발명은 피롤로피리미디논 카복사미드 유도체, 또는 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 함유하는 간세포암 예방 또는 치료용 약학적 조성물에 관한 것으로, 본 발명에 따른 피롤로피리미디논 카복사미드 유도체를 함유하는 조성물은 Cdk1 및 Cdk2를 억제함으로써 인간 간암세포주인 SNU-354 세포의 세포성장을 억제하고, Cdk7 및 Cdk9를 억제함으로써 상기 세포의 세포사멸을 유도하므로 간세포암의 예방 또는 치료에 유용하게 사용될 수 있다.