[5-(4-Methoxyphenyl)thiophen-2-yl]-(3,4,5-trimethoxyphenyl)methanone | 1036271-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [5-(4-Methoxyphenyl)thiophen-2-yl]-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1036271-15-4
• 化学式: C₂₁H₂₀O₅S
• 分子量: 384.453
• InChiKey: SAIZLVAZQVWGTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  82.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dithiocarbonic acid O-ethyl ester S-[2-oxo-2-(3,4,5-trimethoxyphenyl)-ethyl] ester 、 3-氯-3-(4-甲氧基苯基)丙烯醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以34%的产率得到[5-(4-Methoxyphenyl)thiophen-2-yl]-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of thiophene analogues of chalcones

  摘要：

  Chalcones are characterized by possessing an enone moiety between two aromatic rings. A series of chalcone-like agents, in which the double bond of the enone system is embedded within a thiophene ring, were synthesized and evaluated for antiproliferative activity and inhibition of tubulin assembly and colchicine binding to tubulin. The replacement of the double bond with a thiophene maintains antiproliferative activity and therefore must not significantly alter the relative conformation of the two aryl rings. The synthesized compounds were found to inhibit the growth of several cancer cell lines at nanomolar to low micromolar concentrations. In general, all compounds having significant antiproliferative activity inhibited tubulin polymerization with an IC50 < 2 mu M. Several of these compounds caused K562 cells to arrest in the G2/M phase of the cell cycle. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.026

文献信息

• Design, synthesis, and biological evaluation of thiophene analogues of chalcones
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Olga Cruz-Lopez、Delia Preti、Manlio Tolomeo、Stefania Grimaudo、Antonella Di Cristina、Nicola Zonta、Jan Balzarini、Andrea Brancale、Taradas Sarkar、Ernest Hamel

  DOI：10.1016/j.bmc.2008.04.026

  日期：2008.5

  Chalcones are characterized by possessing an enone moiety between two aromatic rings. A series of chalcone-like agents, in which the double bond of the enone system is embedded within a thiophene ring, were synthesized and evaluated for antiproliferative activity and inhibition of tubulin assembly and colchicine binding to tubulin. The replacement of the double bond with a thiophene maintains antiproliferative activity and therefore must not significantly alter the relative conformation of the two aryl rings. The synthesized compounds were found to inhibit the growth of several cancer cell lines at nanomolar to low micromolar concentrations. In general, all compounds having significant antiproliferative activity inhibited tubulin polymerization with an IC50 < 2 mu M. Several of these compounds caused K562 cells to arrest in the G2/M phase of the cell cycle. (C) 2008 Elsevier Ltd. All rights reserved.