Xylocydine

• 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: Xylocydine
• 英文别名: MCS-5A；4-amino-6-bromo-7-[(2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide
• 化学式: C₁₂H₁₄BrN₅O₅
• 分子量: 388.178
• InChiKey: DMXIHKQKBYZIHM-YJMZUNRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  170
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  双氧水 、 4-amino-6-bromo-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)-pyrrolo[2,3-d]pyrimidine 在 ammonium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以52%的产率得到Xylocydine
  参考文献：
  名称：

  Selectivity between N-1 and N-7 nucleosides: regioselective synthesis of BMK-Y101, a potent cdk7 and 9 inhibitor

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.07.132

文献信息

• PHARMACEUTICAL COMBINATION FOR TREATMENT OF CANCER
  申请人：ArQule, Inc.

  公开号：US20200155521A1

  公开（公告）日：2020-05-21

  The present application is drawn to methods of treating a cell proliferative disorder, such as a cancer, comprising administering to a subject in need thereof a therapeutically effective amount of a composition comprising at least one of Compound 1, Compound 2, and Compound 3, or a pharmaceutically acceptable salt, solvate, hydrate, or prodrug thereof, and at least one second therapeutic agent or a pharmaceutically acceptable salt, solvate, hydrate, or prodrug thereof, wherein the cell proliferative disorder is treated.
• 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.