(RS)-6-amino-9-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-9H-purine | 1335000-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (RS)-6-amino-9-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-9H-purine
• 英文别名: 9-(2,3-Dihydro-1,4-benzoxathiin-2-ylmethyl)purin-6-amine
• CAS: 1335000-22-0
• 化学式: C₁₄H₁₃N₅OS
• 分子量: 299.356
• InChiKey: VXYMAODNRFWVRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-hydroxymethyl-1,4-benzoxathiane 、 腺嘌呤 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以30%的产率得到(RS)-6-amino-9-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-9H-purine
  参考文献：
  名称：

  Synthesis and anticancer activity of (RS)-9-(2,3-dihydro-1,4-benzoxaheteroin-2-ylmethyl)-9H-purines

  摘要：

  Herein are reported the synthesis and anticancer activity against the human breast cancer cell line MCF-7 of a series of substituted (RS)-9-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-9H-purine derivatives and (RS)-9-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-9H-purine derivatives. When the Mitsunobu reaction was carried out between (RS)-2,3-dihydro-1,4-benzoxathiin-3-methanol and the heterocyclic bases 6-chloro-, 2,6-dichloro, and 6-bromo-purines under microwave-assisted conditions, a formal 1,4-sulfur migration takes place through two consecutive oxyranium and episulfonium rings, giving rise to the corresponding (RS)-9-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-9H-purine derivatives, previously reported by us. The most active compound (RS)-2,6-dichloro-9-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-9H-purine shows an IC50 = 2.75 +/- 0.02 mu M. When the cancerous cells were treated with this compound, a significant increase of apoptotic cells (70.08 +/- 0.33%) was obtained in relation to the control ones. The induction of the G(2)/M cell cycle arrest and apoptosis by the three most active compounds is associated with increased phosphorylation of eIF2 alpha in human breast cancer cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.046

文献信息

• Synthesis and anticancer activity of (RS)-9-(2,3-dihydro-1,4-benzoxaheteroin-2-ylmethyl)-9H-purines
  作者：Ana Conejo-García、M. Eugenia García-Rubiño、Juan A. Marchal、M. Carmen Núñez、Alberto Ramírez、Sandro Cimino、M. Ángel García、Antonia Aránega、Miguel A. Gallo、Joaquín M. Campos

  DOI：10.1016/j.ejmech.2011.05.046

  日期：2011.9

  Herein are reported the synthesis and anticancer activity against the human breast cancer cell line MCF-7 of a series of substituted (RS)-9-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-9H-purine derivatives and (RS)-9-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-9H-purine derivatives. When the Mitsunobu reaction was carried out between (RS)-2,3-dihydro-1,4-benzoxathiin-3-methanol and the heterocyclic bases 6-chloro-, 2,6-dichloro, and 6-bromo-purines under microwave-assisted conditions, a formal 1,4-sulfur migration takes place through two consecutive oxyranium and episulfonium rings, giving rise to the corresponding (RS)-9-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-9H-purine derivatives, previously reported by us. The most active compound (RS)-2,6-dichloro-9-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-9H-purine shows an IC50 = 2.75 +/- 0.02 mu M. When the cancerous cells were treated with this compound, a significant increase of apoptotic cells (70.08 +/- 0.33%) was obtained in relation to the control ones. The induction of the G(2)/M cell cycle arrest and apoptosis by the three most active compounds is associated with increased phosphorylation of eIF2 alpha in human breast cancer cells. (C) 2011 Elsevier Masson SAS. All rights reserved.