1-(2-fluorophenyl)-3-(3,5-dimethoxyphenyl)prop-2-en-1-one

• 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: 1-(2-fluorophenyl)-3-(3,5-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: 3,5-Dimethoxy-2'-fluorochalcone；3-(3,5-dimethoxyphenyl)-1-(2-fluorophenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₅FO₃
• 分子量: 286.303
• InChiKey: HTHTYBSSRYBPAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2'-氟苯乙酮 、 3,5-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到1-(2-fluorophenyl)-3-(3,5-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Potential cytotoxic and apoptosis inducing agents: synthesis and evaluation of methoxy-substituted chalcones against human lung and cervical cancers

  摘要：

  The role of methoxy group substitution in various positions in both the rings of chalcones on cytotoxicity profile was studied using various synthesized chalcones. The fluorine containing acetophenones when reacted with various methoxy-substituted benzaldehydes in the presence of 10 % sodium hydroxide solution gave the functionalized chalcones. All the synthesized chalcones were confirmed by spectral techniques like FTIR, H-1 NMR, C-13 NMR, and HRMS studies. All the synthesized compounds were screened for their cytotoxicity against various cell lines. The promising compounds were analyzed for cell cycle analysis.

  DOI：

  10.1007/s00044-013-0520-9

文献信息

• Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones
  申请人：Statens Serum Institute

  公开号：US20030065039A1

  公开（公告）日：2003-04-03

  The invention relates to the use of 1,3-bis-aromatic-prop-2-en-1-ones (chalcones), 1,3-bis-aromatic-propan-1-ones (dihydrochalcones), and 1,3-bis-aromatic-prop-2-yn-1-ones for the preparation of pharmaceutical compositions for the treatment or prophylaxis of a number of serious diseases including i) conditions relating to harmful effects of inflammatory cytokines, ii) conditions involving infection by Helicobacter species, iii) conditions involving infection by viruses, iv) neoplastic disorders, and v) conditions caused by microorganisms or parasites. The invention also relates to novel chalcones and dihydrochalcones (especially alkoxy substituted variants) having advantageous substitution patterns with respect to their effect as drug substances, and to methods of preparing them, as well as to pharmaceutical compositions comprising the novel chalcones. Moreover, the present invention relates to a method for the isolation of Leishmania fumarate reductase, QSAR methodologies for selecting potent compounds for the above-mentioned purposes.

  本发明涉及使用1,3-双芳基-丙烯酮（查尔酮）、1,3-双芳基-丙酮（二氢查尔酮）和1,3-双芳基-丙炔酮用于制备用于治疗或预防许多严重疾病的药物组合物，包括i）与炎性细胞因子有害影响有关的情况，ii）涉及幽门螺杆菌感染的情况，iii）涉及病毒感染的情况，iv）恶性肿瘤疾病和v）由微生物或寄生虫引起的情况。本发明还涉及具有有利的替代模式的新型查尔酮和二氢查尔酮（特别是烷氧基取代变体），其作为药物物质的效果，以及制备它们的方法，以及包含新型查尔酮的药物组合物。此外，本发明还涉及一种分离利什曼原虫富马酸还原酶的方法，用于选择上述目的的有效化合物的QSAR方法。