2-tert-butyl-6,7-dihydro-4H-thieno[3,2-b]azepine-5,8-dione | 474543-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-tert-butyl-6,7-dihydro-4H-thieno[3,2-b]azepine-5,8-dione
• CAS: 474543-14-1
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: QSNICPMSYWYTRW-UHFFFAOYSA-N

物化性质

• 沸点：
  415.3±45.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对溴苯肼 、 2-tert-butyl-6,7-dihydro-4H-thieno[3,2-b]azepine-5,8-dione 在 硫酸 、 溶剂黄146 作用下， 反应 2.0h， 以14%的产率得到8-bromo-2-tert-butyl-6,11-dihydro-thieno-[3',2':2,3]azepino[4,5-b]indol-5(4H)-one
  参考文献：
  名称：

  New thiophene analogues of kenpaullone: synthesis and biological evaluation in breast cancer cells

  摘要：

  Thieno analogues of kenpaullone have been synthesized using an established method. We investigated the effect of five structural analogues of kenpaullone on vincristine sensitive and resistant MCF7 (human mammary adenocarcinoma) cells. One analogue, 8-Bromo-6,11-dihydro-thermo-[3',2':2,3]azepino[4,5-b]indol-5(4H)-one (3a), showed an antiproliferative activity in the drug sensitive cell line that led to cell accumulation in G2/M phase. In addition, repression of cdk 1. a G2/M transition key regulator, as well as induction of p21 were observed at the mRNA level. Programmed cell death (apoptosis) was induced in early time treatments and was accompanied by p53 mRNA induction. The antiproliferative and proapoptotic properties of 3a make this CDK inhibitor an interesting candidate for further investigations. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.02.010
• 作为产物：
  描述：

  3-chloro-4,4-dimethylpent-2-enenitrile 在 水 、 potassium hydride 、 potassium carbonate 、 calcium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 2-tert-butyl-6,7-dihydro-4H-thieno[3,2-b]azepine-5,8-dione
  参考文献：
  名称：

  α-亚甲基酮合成新型噻吩并[b]氮杂二酮

  摘要：

  新的取代 6,7-dihydro-4H-thieno[3,2-b]azepine-5,8-diones 由取代的 u-亚甲基酮通过 3-氨基噻吩-2-羧酸烷基酯分 7 步合成.

  DOI：

  10.1055/s-2002-31963

文献信息

• New thiophene analogues of kenpaullone: synthesis and biological evaluation in breast cancer cells
  作者：Laurent Brault、Evelyne Migianu、Adrien Néguesque、Eric Battaglia、Denyse Bagrel、Gilbert Kirsch

  DOI：10.1016/j.ejmech.2005.02.010

  日期：2005.8

  Thieno analogues of kenpaullone have been synthesized using an established method. We investigated the effect of five structural analogues of kenpaullone on vincristine sensitive and resistant MCF7 (human mammary adenocarcinoma) cells. One analogue, 8-Bromo-6,11-dihydro-thermo-[3',2':2,3]azepino[4,5-b]indol-5(4H)-one (3a), showed an antiproliferative activity in the drug sensitive cell line that led to cell accumulation in G2/M phase. In addition, repression of cdk 1. a G2/M transition key regulator, as well as induction of p21 were observed at the mRNA level. Programmed cell death (apoptosis) was induced in early time treatments and was accompanied by p53 mRNA induction. The antiproliferative and proapoptotic properties of 3a make this CDK inhibitor an interesting candidate for further investigations. (c) 2005 Elsevier SAS. All rights reserved.
• Synthesis of New Thieno[b]azepinediones from α-Methylene Ketones
  作者：Evelyne Migianu、Gilbert Kirsch

  DOI：10.1055/s-2002-31963

  日期：——

  New substituted 6,7-dihydro-4H-thieno[3,2-b]azepine-5,8-diones were synthesized in seven steps, starting from substituted u-methylene ketones, via 3-aminothiophene-2-carboxylic acid alkyl esters.

  新的取代 6,7-dihydro-4H-thieno[3,2-b]azepine-5,8-diones 由取代的 u-亚甲基酮通过 3-氨基噻吩-2-羧酸烷基酯分 7 步合成.