1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine | 869578-09-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine
• 英文别名: 1-(3,5-dihydro-2H-4,1-benzoxathiepin-3-yl)-5-methylpyrimidine-2,4-dione
• CAS: 869578-09-6
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: LBLAJTFGUAEGEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine 在 双氧水 作用下， 反应 2.0h， 以50%的产率得到(1RS,3SR)-1-(1-oxo-2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine
  参考文献：
  名称：

  Synthesis of novel 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-uracil and -thymine, and their corresponding S-oxidized derivatives

  摘要：

  On the basis of molecular variations on isosteric replacements from the prototype 1-(2,3-dihydro-5H- 1,4-benzodioxepin-3-yl)-5fluorouracil a series of 3-(2,3-dihydro-5H-4, 1-benzoxathiepin-3-yl)-uracil or -thymine O,N-acetals was prepared. The nature of the cis- and trans-sulfoxide isomers was established by means of their conformational analyses carried out with Sybyl and after comparing the theoretical results with the H-1 NMR responses of the target molecules. (RS)-3-(1,1-Dioxo-2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine and (IS*, 3S*)-1-(1-oxo-3,5-dihydro-2H-4,1-benzoxathiepin-3-yl)thymine were found to be inhibitors of the MCF-7 cell growth. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.065
• 作为产物：
  描述：

  o-hydroxymethylphenylthioacetaldehyde dimethyl acetal 在 三甲基氯硅烷 、 四氯化锡 、 对甲苯磺酸 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine
  参考文献：
  名称：

  Synthesis of novel 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-uracil and -thymine, and their corresponding S-oxidized derivatives

  摘要：

  On the basis of molecular variations on isosteric replacements from the prototype 1-(2,3-dihydro-5H- 1,4-benzodioxepin-3-yl)-5fluorouracil a series of 3-(2,3-dihydro-5H-4, 1-benzoxathiepin-3-yl)-uracil or -thymine O,N-acetals was prepared. The nature of the cis- and trans-sulfoxide isomers was established by means of their conformational analyses carried out with Sybyl and after comparing the theoretical results with the H-1 NMR responses of the target molecules. (RS)-3-(1,1-Dioxo-2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine and (IS*, 3S*)-1-(1-oxo-3,5-dihydro-2H-4,1-benzoxathiepin-3-yl)thymine were found to be inhibitors of the MCF-7 cell growth. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.065

文献信息

• Synthesis of novel 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-uracil and -thymine, and their corresponding S-oxidized derivatives
  作者：M. del Carmen Núñez、Antonio Entrena、Fernando Rodríguez-Serrano、Juan A. Marchal、Antonia Aránega、Miguel Á. Gallo、Antonio Espinosa、Joaquín M. Campos

  DOI：10.1016/j.tet.2005.07.065

  日期：2005.10

  On the basis of molecular variations on isosteric replacements from the prototype 1-(2,3-dihydro-5H- 1,4-benzodioxepin-3-yl)-5fluorouracil a series of 3-(2,3-dihydro-5H-4, 1-benzoxathiepin-3-yl)-uracil or -thymine O,N-acetals was prepared. The nature of the cis- and trans-sulfoxide isomers was established by means of their conformational analyses carried out with Sybyl and after comparing the theoretical results with the H-1 NMR responses of the target molecules. (RS)-3-(1,1-Dioxo-2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine and (IS*, 3S*)-1-(1-oxo-3,5-dihydro-2H-4,1-benzoxathiepin-3-yl)thymine were found to be inhibitors of the MCF-7 cell growth. (c) 2005 Elsevier Ltd. All rights reserved.