6-((4-fluorophenyl)thio)-9H-purine | 736142-69-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-((4-fluorophenyl)thio)-9H-purine
• 英文别名: 6-(4-fluorophenyl)sulfanyl-7H-purine
• CAS: 736142-69-1
• 化学式: C₁₁H₇FN₄S
• 分子量: 246.268
• InChiKey: MTSKQGGVBOTGLP-UHFFFAOYSA-N

物化性质

• 熔点：
  233 °C
• 沸点：
  540.1±40.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (RS)-3-methoxy-2,3-dihydro-5H-1,4-benzodioxepin 、 6-((4-fluorophenyl)thio)-9H-purine 在 四氯化锡 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.08h， 以35%的产率得到7-(3,5-dihydro-2H-1,4-benzodioxepin-3-yl)-6-(4-fluorophenyl)sulfanylpurine
  参考文献：
  名称：

  Regiospecific microwave-assisted synthesis and cytotoxic activity against human breast cancer cells of (RS)-6-substituted-7- or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H- or -9H-purines

  摘要：

  Extended studies on the synthesis and pharmacological evaluation of (RS)-6-substituted-7 or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H- or -9H-purines are presented. The microwave-assisted organic synthesis has provided faster access to the target compounds with the advantage of selective obtaining the N-7 ' or N-9 ' regioisomers simplifying their isolation. To test the behaviour of the products (including the purine bases) on cellular systems, cytotoxic activity against the MCF-7 human breast cancer cell line was determined, and the three most active compounds were used to study the cell cycle distribution and apoptosis in the MCF-7 cell line. (c) 2007 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.025
• 作为产物：
  描述：

  对氟苯硫酚 、 6-氯嘌呤 以 乙醇 为溶剂， 反应 16.0h， 以56%的产率得到6-((4-fluorophenyl)thio)-9H-purine
  参考文献：
  名称：

  鉴定新的芳基硫醚衍生物作为斑马鱼模型中的抗黑色素生成剂。

  摘要：

  合成了一系列芳基硫醚衍生物，并评估了它们的抗黑色素生成活性。包括3e，3i和3q在内的几种化合物均表现出良好的抗黑色素生成活性。在这些衍生物中，化合物3i对黑色素的合成显示出良好的抑制作用，并且在重建的人眼和皮肤组织中没有毒性。

  DOI：

  10.1016/j.bmcl.2020.127201

文献信息

• Verwendung von Purinderivaten als selektive Kinase-Inhibitoren
  申请人：MERCKLE GMBH

  公开号：EP1444982A1

  公开（公告）日：2004-08-11

  Die vorliegende Erfindung betrifft die Verwendung von Purinderivaten zur selektiven Inhibierung von Kinasen. Die Verbindungen sind daher zur Behandlung von Erkrankungen brauchbar, welche in Zusammenhang mit der Kinase-Aktivität stehen.

  本发明涉及使用嘌呤衍生物选择性抑制激酶。因此，这些化合物可用于治疗与激酶活性有关的疾病。
• Synthesis and Biological Testing of Purine Derivatives as Potential ATP-Competitive Kinase Inhibitors
  作者：Stefan A. Laufer、David M. Domeyer、Thomas R. F. Scior、Wolfgang Albrecht、Dominik R. J. Hauser

  DOI：10.1021/jm0408767

  日期：2005.2.1

  On the basis of ATP adenine, a series of adenine and purine derivatives was prepared and tested for their ability to inhibit a spectrum of disease-related kinases. There has been scant research investigating the potential of cosubstrate derived kinase inhibitors for other kinases than CDKs. Our inhibitor design combined the purine system from the original cosubstrate ATP and phenyl moieties in order to explore possible interactions with the different regions of the ATP binding site in several disease-related protein kinases. There have been a number of hits for the assayed substances, which led us to conclude that the spectrum of compounds may prove to be a valuable tool kit for the evaluation of bonding and selectivity patterns for a wide variety of kinases.
• Copper Catalyzed Three-Component Ullmann C–S Coupling in PEG for the Synthesis of 6-Aryl/alkylthio-purines
  作者：Panpan Zhang、Yunfang Liu、Xulian Li、Geling Siri、Jieyuan Wang、Zhen Li、Yajun Jian、Ziwei Gao

  DOI：10.1021/acs.joc.3c02116

  日期：2024.2.16
• Identification of new arylsulfide derivatives as anti-melanogenic agents in a zebrafish model
  作者：Se Hwan Ahn、Kyu-Seok Hwang、Dae-Seop Shin、Seong Soon Kim、Jung Yoon Yang、Byung Hoi Lee、Eun Jung Bae、Byeong Wook Choi、Myung Ae Bae、Jin Hee Ahn

  DOI：10.1016/j.bmcl.2020.127201

  日期：2020.7

  A series of aryl sulfide derivatives was synthesized and evaluated for their anti-melanogenic activities. Several compounds, including 3e, 3i and 3q exhibited good anti-melanogenic activities. Among the derivatives, compound 3i showed good inhibitory effects against melanin synthesis and showed no toxicity in reconstituted human eye and skin tissues.

  合成了一系列芳基硫醚衍生物，并评估了它们的抗黑色素生成活性。包括3e，3i和3q在内的几种化合物均表现出良好的抗黑色素生成活性。在这些衍生物中，化合物3i对黑色素的合成显示出良好的抑制作用，并且在重建的人眼和皮肤组织中没有毒性。
• Regiospecific microwave-assisted synthesis and cytotoxic activity against human breast cancer cells of (RS)-6-substituted-7- or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H- or -9H-purines
  作者：Ana Conejo-García、María C. Núñez、Juan A. Marchal、Fernando Rodríguez-Serrano、Antonia Aránega、Miguel A. Gallo、Antonio Espinosa、Joaquín M. Campos

  DOI：10.1016/j.ejmech.2007.10.025

  日期：2008.8

  Extended studies on the synthesis and pharmacological evaluation of (RS)-6-substituted-7 or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H- or -9H-purines are presented. The microwave-assisted organic synthesis has provided faster access to the target compounds with the advantage of selective obtaining the N-7 ' or N-9 ' regioisomers simplifying their isolation. To test the behaviour of the products (including the purine bases) on cellular systems, cytotoxic activity against the MCF-7 human breast cancer cell line was determined, and the three most active compounds were used to study the cell cycle distribution and apoptosis in the MCF-7 cell line. (c) 2007 Elsevier Masson SAS. All fights reserved.