3-Anthracen-9-yl-1-thiophen-2-ylprop-2-en-1-one | 36715-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-Anthracen-9-yl-1-thiophen-2-ylprop-2-en-1-one
• 英文别名: 3-anthracen-9-yl-1-thiophen-2-ylprop-2-en-1-one
• CAS: 36715-63-6
• 化学式: C₂₁H₁₄OS
• 分子量: 314.408
• InChiKey: TUAYRVSZTWAYRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Anthracen-9-yl-1-thiophen-2-ylprop-2-en-1-one 在 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 {(4-[3-(thiophen-2-yl)-5-anthracen-9-yl-4,5-dihydropyrazol-1-yl]phenyl)sulfonyl}-N'-p-methoxyphenylurea
  参考文献：
  名称：

  Novel benzenesulfonylureas containing thiophenylpyrazoline moiety as potential antidiabetic and anticancer agents

  摘要：

  In the present study a library of twenty six benzenesulfonylureas containing thiophenylpyrazoline moiety has been synthesized. All the compounds were docked against PPAR-gamma target. Most of the compounds displayed higher dock score than standard drugs, glibenclamide and rosiglitazone. All the synthesized compounds were primarily evaluated for their antidiabetic effect by oral glucose tolerance test. Further assessment of antidiabetic potential of sixteen active compounds was then done on STZ induced diabetic model. The results of in vivo activity by both the methods were found to be consistent with each other as well as with docking studies. Change in body weight of STZ induced animals post treatment was also assessed at the end of study. In vitro PPAR-gamma transactivation assay was performed on active compounds in order to validate docking results and the most active compound 3k was also shown to elevate gene expression of PPAR-gamma. Furthermore, the compounds were screened by National Cancer Institute, Bethesda for anticancer effect and two compounds 3h and 3i were selected at one dose level since they exhibited sensitivity towards tumor cell lines (mainly melanoma). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.044
• 作为产物：
  描述：

  2-乙酰基噻吩 、 9-蒽甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以80%的产率得到3-Anthracen-9-yl-1-thiophen-2-ylprop-2-en-1-one
  参考文献：
  名称：

  Synthesis, Spectral Studies and Anti-Inflammatory Activity of 2-Acetyl Thiophene

  摘要：

  一些新的查尔酮通过2-乙酰基噻吩与不同芳香醛在40%碱性条件下缩合合成。合成的化合物通过光谱数据进行鉴定，并进行抗炎活性筛选。其中一些化合物表现出中等到可观的抗炎活性。

  DOI：

  10.1155/2010/404715

文献信息

• Synthesis, Spectral Studies and Anti-Inflammatory Activity of 2-Acetyl Thiophene
  作者：B. Ramesh、B. Someswara Rao

  DOI：10.1155/2010/404715

  日期：——

  Some new chalcones have been synthesized by the condensation of 2-acetyl thiophene with various aromatic aldehydes in 40% alkali. The synthesized compounds were identified by spectral data and screened for anti-inflammatory activity. Some of these compounds showed moderate to considerable anti-inflammatory activity.

  一些新的查尔酮通过2-乙酰基噻吩与不同芳香醛在40%碱性条件下缩合合成。合成的化合物通过光谱数据进行鉴定，并进行抗炎活性筛选。其中一些化合物表现出中等到可观的抗炎活性。
• Novel benzenesulfonylureas containing thiophenylpyrazoline moiety as potential antidiabetic and anticancer agents
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Syed Shafi、Yakub Ali、Perwez Alam、M.A.Q. Pasha、Abhijeet Dhulap、Sameena Bano、Syed Nazreen、Saqlain Haider

  DOI：10.1016/j.bmcl.2014.09.044

  日期：2014.11

  In the present study a library of twenty six benzenesulfonylureas containing thiophenylpyrazoline moiety has been synthesized. All the compounds were docked against PPAR-gamma target. Most of the compounds displayed higher dock score than standard drugs, glibenclamide and rosiglitazone. All the synthesized compounds were primarily evaluated for their antidiabetic effect by oral glucose tolerance test. Further assessment of antidiabetic potential of sixteen active compounds was then done on STZ induced diabetic model. The results of in vivo activity by both the methods were found to be consistent with each other as well as with docking studies. Change in body weight of STZ induced animals post treatment was also assessed at the end of study. In vitro PPAR-gamma transactivation assay was performed on active compounds in order to validate docking results and the most active compound 3k was also shown to elevate gene expression of PPAR-gamma. Furthermore, the compounds were screened by National Cancer Institute, Bethesda for anticancer effect and two compounds 3h and 3i were selected at one dose level since they exhibited sensitivity towards tumor cell lines (mainly melanoma). (C) 2014 Elsevier Ltd. All rights reserved.