2'-benzenesulphonamidechalcone | 124856-90-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2'-benzenesulphonamidechalcone
• 英文别名: N-[2-(3-Phenylacryloyl)phenyl]benzenesulfonamide；N-[2-(3-phenylprop-2-enoyl)phenyl]benzenesulfonamide
• CAS: 124856-90-2
• 化学式: C₂₁H₁₇NO₃S
• 分子量: 363.437
• InChiKey: QPLKHWKLVFJHHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2'-benzenesulphonamidechalcone 在 quinine 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以70%的产率得到
  参考文献：
  名称：

  使用有机催化6-内基Aza-Michael加成对映体合成氮杂黄酮

  摘要：

  已经描述了使用有机催化6-内氮杂-迈克尔加成反应制备高度对映体富集的氮杂黄酮的方法。制备了各种2-芳基，2-乙烯基和2-甲基氮杂黄烷酮，收率高（53-84％）和出色的对映选择性（97.6：2.4至99.3：0.7 er）。

  DOI：

  10.1002/adsc.201300920
• 作为产物：
  描述：

  苯甲醛 在 三乙胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2'-benzenesulphonamidechalcone
  参考文献：
  名称：

  Synthesis, anti-inflammatory and antioxidant activity of ring-A-monosubstituted chalcone derivatives

  摘要：

  A library of ring-A-monosubstituted chalcone derivatives (4a-4i, 5a and 5b) was designed and synthesised. The structures as well as the identities of these compounds were established on the basis of spectral (H-1 NMR, C-13 NMR, FT-IR and Mass) and elemental (C, H, N) analyses. All the derivatives were evaluated for their anti-inflammatory and antioxidant activities in vitro using the inhibition of protein denaturation and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, respectively. The results indicated a promising anti-inflammatory activity for most of the synthesised compounds with many derivatives showing activities similar to or greater than that of the standard. The sulphonamide-substituted chalcones 4h, 4i, 5a and 5b were found to be the most active derivatives across the concentration range tested. However, all the derivatives exhibited rather mild antioxidant activity compared to the ascorbic acid standard. Interestingly, it was observed that the unsubstituted parent chalcone was one of the optimal compounds with only the trifluoromethyl analogue 4a showing better activity as an antioxidant. The two regioisomeric aminochalcones and 4'-cyanochalcone 4b also seemed to possess decent antioxidant potential.

  DOI：

  10.1007/s00044-014-1007-z

文献信息

• Synthesis, anti-inflammatory and antioxidant activity of ring-A-monosubstituted chalcone derivatives
  作者：Hiba Iqbal、Visakh Prabhakar、Atul Sangith、Baby Chandrika、Ranganathan Balasubramanian

  DOI：10.1007/s00044-014-1007-z

  日期：2014.10

  A library of ring-A-monosubstituted chalcone derivatives (4a-4i, 5a and 5b) was designed and synthesised. The structures as well as the identities of these compounds were established on the basis of spectral (H-1 NMR, C-13 NMR, FT-IR and Mass) and elemental (C, H, N) analyses. All the derivatives were evaluated for their anti-inflammatory and antioxidant activities in vitro using the inhibition of protein denaturation and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, respectively. The results indicated a promising anti-inflammatory activity for most of the synthesised compounds with many derivatives showing activities similar to or greater than that of the standard. The sulphonamide-substituted chalcones 4h, 4i, 5a and 5b were found to be the most active derivatives across the concentration range tested. However, all the derivatives exhibited rather mild antioxidant activity compared to the ascorbic acid standard. Interestingly, it was observed that the unsubstituted parent chalcone was one of the optimal compounds with only the trifluoromethyl analogue 4a showing better activity as an antioxidant. The two regioisomeric aminochalcones and 4'-cyanochalcone 4b also seemed to possess decent antioxidant potential.
• Enantioselective Synthesis of Azaflavanones Using Organocatalytic 6-<i>endo</i>Aza-Michael Addition
  作者：Shuanghua Cheng、Lili Zhao、Shouyun Yu

  DOI：10.1002/adsc.201300920

  日期：2014.3.24

  A method to prepare highly enantioenriched azaflavanones using an organocatalytic 6‐endo aza‐Michael addition has been described. A variety of 2‐aryl‐, 2‐vinyl‐ and 2‐methylazaflavanones were prepared in good yields (53–84%) and excellent enantioselectivities (97.6:2.4 to 99.3:0.7 er).

  已经描述了使用有机催化6-内氮杂-迈克尔加成反应制备高度对映体富集的氮杂黄酮的方法。制备了各种2-芳基，2-乙烯基和2-甲基氮杂黄烷酮，收率高（53-84％）和出色的对映选择性（97.6：2.4至99.3：0.7 er）。