二(3,5-二甲基环己基)硫酸钾 | 222631-55-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 二(3,5-二甲基环己基)硫酸钾
• 英文名称: 2,4-bis-O-benzyl-5-nitro-6-β-dimethylaminovinylpyrimidine
• 英文别名: 2,4-bis-benzyloxy-5-nitro-6-dimethylaminovinyl pyrimidine；2,4-dibenzyloxy-6-(2-dimethylaminoethenyl)-5-nitropyrimidine；2,4-Dibenzyloxy-6-(2-dimethylaminovinyl)-5-nitropyrimidine；N,N-dimethyl-2-[5-nitro-2,6-bis(phenylmethoxy)pyrimidin-4-yl]ethenamine
• CAS: 222631-55-2
• 化学式: C₂₂H₂₂N₄O₄
• 分子量: 406.441
• InChiKey: NDYMCXQFLHOHNI-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C
• 沸点：
  630.9±65.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二(3,5-二甲基环己基)硫酸钾 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 溶剂黄146 、 锌 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：

  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
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 2,4-bis-O-benzyl-6-methyl-5-nitro pyrimidine 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 3.0h， 生成 二(3,5-二甲基环己基)硫酸钾
  参考文献：
  名称：

  Process for preparing 2-pyrrolidinyl-1H-pyrrolo[3,2-d]pyrimidine inhibitors of nucleoside metabolism

  摘要：

  将公式（I）的化合物制备过程翻译成中文： 其中B选择自OH、NH2、NHR、H或卤素；D选择自OH、NH2、NHR、H、卤素或SCH3；R是可选择取代的烷基、芳基烷基或芳基；Z选择自OH、氢、卤素、羟基、SQ或OQ，Q是可选择取代的烷基、芳基烷基或芳基；或其互变异构体；或其药学上可接受的盐；或其酯；或其前药，包括将公式（II）的化合物与通过从公式（XIX）的化合物中提取溴或碘原子而产生的负离子反应，形成公式（XX）的化合物。公式（XX）的化合物经N-和O去保护得到公式（I）的化合物。

  公开号：

  US06693193B1

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。
• Process for preparing 2-pyrrolidinyl-1H-pyrrolo[3,2-d]pyrimidine inhibitors of nucleoside metabolism
  申请人：Industrial Research Limited

  公开号：US06693193B1

  公开（公告）日：2004-02-17

  A process of preparing a compound of the formula (I) wherein B is chosen from OH, NH2, NHR, H or halogen; D is chosen from OH, NH2, NHR, H halogen or SCH3; R is an optionally substituted alkyl, aralkyl or aryl group; and Z is selected from OH, hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted all, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof, which comprises reacting a compound of the formula (II)  with an anion produced by abstraction of the bromine or iodine atom from a compound of formula (XIX),  to form a compound of formula (XX) The compound of formula (XX) is N- and O-deprotected to obtain the compound of formula (I).

  将公式（I）的化合物制备过程翻译成中文： 其中B选择自OH、NH2、NHR、H或卤素；D选择自OH、NH2、NHR、H、卤素或SCH3；R是可选择取代的烷基、芳基烷基或芳基；Z选择自OH、氢、卤素、羟基、SQ或OQ，Q是可选择取代的烷基、芳基烷基或芳基；或其互变异构体；或其药学上可接受的盐；或其酯；或其前药，包括将公式（II）的化合物与通过从公式（XIX）的化合物中提取溴或碘原子而产生的负离子反应，形成公式（XX）的化合物。公式（XX）的化合物经N-和O去保护得到公式（I）的化合物。
• Inhibitors of nucleoside metabolism
  申请人：——

  公开号：US20020061898A1

  公开（公告）日：2002-05-23

  The present invention provides novel nucleoside-analogue compounds that are effective inhibitors of purine nucleoside phosphorylase (PNP), purine phosphoribosyltransferases (PPRT), and/or nucleoside hydrolases. Also provided are tautomers, esters, prodrugs, and pharmaceutically-acceptable salts of the compounds disclosed herein. The present invention further provides the use of these compounds as pharmaceuticals. The present invention also discloses pharmaceutical compositions containing these compounds. Finally, the present invention provides processes for preparing these compounds.

  本发明提供了新型核苷类似物化合物，它们是嘌呤核苷酸磷酸酶（PNP）、嘌呤磷酸核糖转移酶（PPRT）和/或核苷水解酶的有效抑制剂。此外，还提供了这些化合物的互变异构体、酯、前药和药学上可接受的盐。本发明进一步提供了这些化合物作为药物的用途。本发明还揭示了含有这些化合物的制药组合物。最后，本发明提供了制备这些化合物的过程。
• 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。
• 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.