7-(4-(6-chlorobenzo[d]thiazol-2-ylamino)butoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-(4-(6-chlorobenzo[d]thiazol-2-ylamino)butoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one
• 英文别名: 7-[4-[(6-Chloro-1,3-benzothiazol-2-yl)amino]butoxy]-5-hydroxy-2-phenylchromen-4-one；7-[4-[(6-chloro-1,3-benzothiazol-2-yl)amino]butoxy]-5-hydroxy-2-phenylchromen-4-one
• 化学式: C₂₆H₂₁ClN₂O₄S
• 分子量: 492.983
• InChiKey: HSLHZKAIXJMFAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  白杨素 在 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 24.0h， 生成 7-(4-(6-chlorobenzo[d]thiazol-2-ylamino)butoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  Chrysin–benzothiazole conjugates as antioxidant and anticancer agents

  摘要：

  7-(4-Bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, obtained from chrysin with 1,4-dibromobutane, was combined with a wide range of 6-substituted 2-aminobenzthiazoles, which had been prepared from the corresponding anilines with potassium thiocyanate. Free radical scavenging efficacies of newer analogues were measured using DPPH and ABTS assays, in addition to the assessment of their anticancer activity against cervical cancer cell lines (HeLa and CaSki) and ovarian cancer cell line (SK-OV-3) implementing the SRB assay. Cytotoxicity of titled compounds was checked using Madin-Darby canine kidney (MDCK) non-cancer cell line. Overall, 6a-r indicated remarkable antioxidant power as DPPH center dot and ABTS(center dot+) scavengers; particularly the presence of halogen(s) (6g, 6h, 6j-6l) was favourable with IC50 values comparable to the control ascorbic acid. Unsubstituted benzothiazole ring favored the activity of resultant compounds (6a and 6r) against HeLa cell line, whereas presence of chlorine (6g) or a di-fluoro group (6k) was a key to exert strong action against CaSki. Moreover, a mono-fluoro (6j) and a ketonic functionality (6o) were beneficial to display anticipated anticancer effects against ovarian cancer cell line SK-OV-3. The structural assignments of the new products were done on the basis of IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.052

文献信息

• Chrysin–benzothiazole conjugates as antioxidant and anticancer agents
  作者：Bhupendra M. Mistry、Rahul V. Patel、Young-Soo Keum、Doo Hwan Kim

  DOI：10.1016/j.bmcl.2015.10.052

  日期：2015.12

  7-(4-Bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, obtained from chrysin with 1,4-dibromobutane, was combined with a wide range of 6-substituted 2-aminobenzthiazoles, which had been prepared from the corresponding anilines with potassium thiocyanate. Free radical scavenging efficacies of newer analogues were measured using DPPH and ABTS assays, in addition to the assessment of their anticancer activity against cervical cancer cell lines (HeLa and CaSki) and ovarian cancer cell line (SK-OV-3) implementing the SRB assay. Cytotoxicity of titled compounds was checked using Madin-Darby canine kidney (MDCK) non-cancer cell line. Overall, 6a-r indicated remarkable antioxidant power as DPPH center dot and ABTS(center dot+) scavengers; particularly the presence of halogen(s) (6g, 6h, 6j-6l) was favourable with IC50 values comparable to the control ascorbic acid. Unsubstituted benzothiazole ring favored the activity of resultant compounds (6a and 6r) against HeLa cell line, whereas presence of chlorine (6g) or a di-fluoro group (6k) was a key to exert strong action against CaSki. Moreover, a mono-fluoro (6j) and a ketonic functionality (6o) were beneficial to display anticipated anticancer effects against ovarian cancer cell line SK-OV-3. The structural assignments of the new products were done on the basis of IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. (C) 2015 Elsevier Ltd. All rights reserved.