N-(tert-butyl)-2-oxo-2-phenylethane-1-sulfonamide | 1432615-78-5

• 英文名称: N-(tert-butyl)-2-oxo-2-phenylethane-1-sulfonamide
• 英文别名: N-tert-butyl-2-oxo-2-phenylethanesulfonamide
• CAS: 1432615-78-5
• 化学式: C₁₂H₁₇NO₃S
• 分子量: 255.338
• InChiKey: XUKYDWPZQQADAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(tert-butyl)-2-oxo-2-phenylethane-1-sulfonamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以93 %的产率得到2-oxo-2-phenylethanesulphonamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Chalconesulfonamides: En Route to Proapoptotic Agents with Antiestrogenic Potency

  摘要：

  Breast and other estrogen receptor α-positive cancers tend to develop resistance to existing drugs. Chalcone derivatives possess anticancer activity based on their ability to form covalent bonds with targets acting as Michael acceptors. This study aimed to evaluate the anticancer properties of a series of chalcones (7a–l) with a sulfonamide group attached to the vinyl ketone moiety. Chalconesulfonamides showed a potent antiproliferative effect at low micromolar concentrations against several cancer cell lines, including ERα-positive 4-hydroxytamoxifen-resistant MCF7/HT2. Immunoblotting of samples treated with the lead compound 7e revealed its potent antiestrogenic activity (ERα/GREB1 axis) and induction of PARP cleavage (an apoptosis marker) in breast cancer cells. The obtained compounds represent a promising basis for further development of targeted drugs blocking hormone pathways in cancer cells.

  DOI：

  10.3390/ph17010032
• 作为产物：
  描述：

  N-(叔丁基)-甲磺酰胺 在 chromium(VI) oxide 、 硫酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 N-(tert-butyl)-2-oxo-2-phenylethane-1-sulfonamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Chalconesulfonamides: En Route to Proapoptotic Agents with Antiestrogenic Potency

  摘要：

  Breast and other estrogen receptor α-positive cancers tend to develop resistance to existing drugs. Chalcone derivatives possess anticancer activity based on their ability to form covalent bonds with targets acting as Michael acceptors. This study aimed to evaluate the anticancer properties of a series of chalcones (7a–l) with a sulfonamide group attached to the vinyl ketone moiety. Chalconesulfonamides showed a potent antiproliferative effect at low micromolar concentrations against several cancer cell lines, including ERα-positive 4-hydroxytamoxifen-resistant MCF7/HT2. Immunoblotting of samples treated with the lead compound 7e revealed its potent antiestrogenic activity (ERα/GREB1 axis) and induction of PARP cleavage (an apoptosis marker) in breast cancer cells. The obtained compounds represent a promising basis for further development of targeted drugs blocking hormone pathways in cancer cells.

  DOI：

  10.3390/ph17010032

文献信息

• Asymmetric Hydrogenation of β-Keto Sulfonamides and β-Keto Sulfones with a Chiral Cationic Ruthenium Diamine Catalyst
  作者：Xiao-Fei Huang、Shao-Yun Zhang、Zhi-Cong Geng、Chun-Yuen Kwok、Peng Liu、Hai-Yan Li、Xing-Wang Wang

  DOI：10.1002/adsc.201300331

  日期：2013.10.11

  AbstractOptically active β‐hydroxy sulfonamides and β‐hydroxy sulfones are very important building blocks for the preparation of bioactive compounds and pharmaceuticals. In this work, a highly efficient asymmetric hydrogenation of β‐keto sulfonamides and β‐keto sulfones has been developed using the phosphine‐free chiral ruthenium complex Ru(OTf)(TsDPEN)(η6‐p‐cymene) as the catalyst, to afford the corresponding β‐hydroxy sulfonamides and β‐hydroxy sulfones in high yields with excellent optical purities. In addition, a cascade asymmetric hydrogenation/dynamic kinetic resolution (DKR) of racemic cyclic β‐keto sulfonamides and β‐keto sulfones was also realized using the same catalyst, to give the corresponding chiral cyclic β‐hydroxy sulfonamides and β‐hydroxy sulfones in good yields with excellent enantio‐ and diastereoselectivities.magnified image