7-iodo-2,4-bis-benzyloxy-5H-pyrrolo[3,2-d]pyrimidine | 1446175-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 7-iodo-2,4-bis-benzyloxy-5H-pyrrolo[3,2-d]pyrimidine
• 英文别名: 7-iodo-2,4-bis(phenylmethoxy)-5H-pyrrolo[3,2-d]pyrimidine
• CAS: 1446175-04-7
• 化学式: C₂₀H₁₆IN₃O₂
• 分子量: 457.27
• InChiKey: FEGSFOMGBUDOJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-iodo-2,4-bis-benzyloxy-5H-pyrrolo[3,2-d]pyrimidine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三正丁胺 、 三苯胂 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.0h， 生成 2,4-bis-benzyloxy-5H-7-(β-D-glycero-pentofuran-3′-ulos-1′-yl)pyrrolo[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
• 作为产物：
  描述：

  二(3,5-二甲基环己基)硫酸钾 在 N-碘代丁二酰亚胺 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 生成 7-iodo-2,4-bis-benzyloxy-5H-pyrrolo[3,2-d]pyrimidine
  参考文献：
  名称：

  Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.06.025

文献信息

• THIENO- AND PYRROLOPYRIMIDINE ANALOGUES AS ANTICANCER AGENTS AND METHODS OF USE THEREOF
  申请人：UNIVERSITY OF MARYLAND, BALTIMORE COUNTY

  公开号：US20160257696A1

  公开（公告）日：2016-09-08

  The present invention provides for the design and synthesis of halogenated thieno- and pyrrolopyrimidine compounds that exhibit cancer proliferation inhibitory activity and the use thereof for cancer treatment.

  本发明提供了设计和合成卤代噻吩和吡咯并嘧啶化合物的方法，这些化合物表现出抑制癌细胞增殖活性，并可用于癌症治疗。
• Thieno- and pyrrolopyrimidine analogues as anticancer agents and methods of use thereof
  申请人：UNIVERSITY OF MARYLAND, BALTIMORE COUNTY

  公开号：US09434742B1

  公开（公告）日：2016-09-06

  The present invention provides for the design and synthesis of halogenated thieno- and pyrrolopyrimidine compounds that exhibit cancer proliferation inhibitory activity and the use thereof for cancer treatment.

  本发明提供了卤代噻吩和吡咯并嘧啶化合物的设计和合成，这些化合物具有抑制癌细胞增殖的活性，并可用于癌症治疗。
• Thieno- and pyrrolopyrimidine analogues and prodrugs thereof as anticancer agents and methods of use thereof
  申请人：UNIVERSITY OF MARYLAND, BALTIMORE COUNTY

  公开号：US10646490B2

  公开（公告）日：2020-05-12

  The present invention provides for the design and synthesis of halogenated thieno- and pyrrolopyrimidine compounds and prodrugs thereof that exhibit cancer proliferation inhibitory activity and the use thereof for cancer treatment.

  本发明提供了具有癌症增殖抑制活性的卤代噻吩和吡咯并嘧啶化合物及其原药的设计和合成，以及其在癌症治疗中的应用。
• THIENO- AND PYRROLOPYRIMIDINE ANALOGUES AND PRODRUGS THEREOF AS ANTICANCER AGENTS AND METHODS OF USE THEREOF
  申请人：UNIVERSITY OF MARYLAND, BALTIMORE COUNTY

  公开号：US20190160071A1

  公开（公告）日：2019-05-30

  The present invention provides for the design and synthesis of halogenated thieno- and pyrrolopyrimidine compounds and prodrugs thereof that exhibit cancer proliferation inhibitory activity and the use thereof for cancer treatment.
• US9434742B1
  申请人：——

  公开号：US9434742B1

  公开（公告）日：2016-09-06