2,4-bis-benzyloxy-5-N-boc-7-iodopyrrolo[3,2-d]pyrimidine | 1446175-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2,4-bis-benzyloxy-5-N-boc-7-iodopyrrolo[3,2-d]pyrimidine
• CAS: 1446175-09-2
• 化学式: C₂₅H₂₄IN₃O₄
• 分子量: 557.388
• InChiKey: CVSAXIMVNGCTGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.47
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4,5-哒嗪二醇,六氢-3-(羟甲基)-,(3R,4R,5R)- 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,4-bis-benzyloxy-5-N-boc-7-iodopyrrolo[3,2-d]pyrimidine
  参考文献：
  名称：

  Synthesis of 2′-Deoxy-9-deaza Nucleosides Using Heck Methodology

  摘要：

  During the synthesis of a series of 2'-deoxy-9-deaza nucleosides using Heck methodology, the necessity for a pyrrole protecting group was discovered. The results of this brief study revealed that the benzyloxymethyl (BOM) group proved optimal, and Heck coupling using Jeffery conditions increased the coupling yield significantly. The results are reported herein.

  DOI：

  10.1021/jo400913k

文献信息

• Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines
  作者：Kartik W. Temburnikar、Christina R. Ross、Gerald M. Wilson、Jan Balzarini、Brian M. Cawrse、Katherine L. Seley-Radtke

  DOI：10.1016/j.bmc.2015.06.025

  日期：2015.8

  In vitro evaluation of the halogenated pyrrolo[3,2-d]pyrimidines identified antiproliferative activities in compounds 1 and 2 against four different cancer cell lines. Upon screening of a series of pyrrolo[3, 2-d] pyrimidines, the 2,4-Cl compound 1 was found to exhibit antiproliferative activity at low micromolar concentrations. Introduction of iodine at C7 resulted in significant enhancement of potency by reducing the IC50 into sub-micromolar levels, thereby suggesting the importance of a halogen at C7. This finding was further supported by an increased antiproliferative effect for 4 as compared to 3. Cell-cycle and apoptosis studies conducted on the two potent compounds 1 and 2 showed differences in their cytotoxic mechanisms in triple negative breast cancer MDA-MB-231 cells, wherein compound 1 induced cells to accumulate at the G2/M stage with little evidence of apoptotic death. In contrast, compound 2 robustly induced apoptosis with concomitant G2/M cell cycle arrest in this cell model. (C) 2015 Elsevier Ltd. All rights reserved.