3-methoxy-2,3-dihydro-5H-4,1-benzoxathiepin | 869578-05-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-methoxy-2,3-dihydro-5H-4,1-benzoxathiepin
• 英文别名: 3-methoxy-3,5-dihydro-2H-4,1-benzoxathiepine
• CAS: 869578-05-2
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: CMTAXXNQJFGCRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-2,3-dihydro-5H-4,1-benzoxathiepin 在 三甲基氯硅烷 、 sodium hydride 、 六甲基二硅氮烷 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 25.0h， 生成 6-methoxy-9-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-9H-purine
  参考文献：
  名称：

  6′-Chloro-7- or 9-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-7H- or 9H-purines and their corresponding sulfones as a new family of cytotoxic drugs

  摘要：

  A series of 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)pyrimidine derivatives were synthesized and two of them (8 and 9) showed a modest antiproliferative activity against the MCF-7 breast cancer cell line. We then decided to change the pyrimidine base for the more lipophilic 6'-chloropurine, and the N-9'purine (15) and N-7' purine (17) were obtained. The sulfone N-7'-alkylated-6-chloropurine 18 was the most active derivative. Compound 17 was found to be slightly more active than its regioisomer 15, with an activity similar to that of 5-fluorouracil as a reference drug. Encouraged by these values, we tested these compounds against both the HT-29 human colon cancer cell line and the IEC-6 normal rat intestinal epithelial cell line, and 15 was found to be 12.7-fold more active against HT-29 than versus IEC-6. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.023
• 作为产物：
  描述：

  2-巯基苯甲醇 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 3-methoxy-2,3-dihydro-5H-4,1-benzoxathiepin
  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.
• 6′-Chloro-7- or 9-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-7H- or 9H-purines and their corresponding sulfones as a new family of cytotoxic drugs
  作者：María C. Núñez、Fernando Rodríguez-Serrano、Juan A. Marchal、Octavio Caba、Antonia Aránega、Miguel A. Gallo、Antonio Espinosa、Joaquín M. Campos

  DOI：10.1016/j.tet.2006.10.023

  日期：2007.1

  A series of 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)pyrimidine derivatives were synthesized and two of them (8 and 9) showed a modest antiproliferative activity against the MCF-7 breast cancer cell line. We then decided to change the pyrimidine base for the more lipophilic 6'-chloropurine, and the N-9'purine (15) and N-7' purine (17) were obtained. The sulfone N-7'-alkylated-6-chloropurine 18 was the most active derivative. Compound 17 was found to be slightly more active than its regioisomer 15, with an activity similar to that of 5-fluorouracil as a reference drug. Encouraged by these values, we tested these compounds against both the HT-29 human colon cancer cell line and the IEC-6 normal rat intestinal epithelial cell line, and 15 was found to be 12.7-fold more active against HT-29 than versus IEC-6. (c) 2006 Elsevier Ltd. All rights reserved.