4-(3-fluoro-2-hydroxy-phenyl)-but-3-en-2-one | 790720-63-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(3-fluoro-2-hydroxy-phenyl)-but-3-en-2-one
• 英文别名: 4-(3-Fluoro-2-hydroxyphenyl)but-3-en-2-one；(E)-4-(3-fluoro-2-hydroxyphenyl)but-3-en-2-one
• CAS: 790720-63-7
• 化学式: C₁₀H₉FO₂
• 分子量: 180.179
• InChiKey: FBEFWOVSMNHNGN-AATRIKPKSA-N

物化性质

• 熔点：
  167-168 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  300.5±27.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甘草次酸 、 4-(3-fluoro-2-hydroxy-phenyl)-but-3-en-2-one 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 [2-fluoro-6-[(E)-3-oxobut-1-enyl]phenyl] (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
  参考文献：
  名称：

  Anti-tumor agents 255: Novel glycyrrhetinic acid–dehydrozingerone conjugates as cytotoxic agents

  摘要：

  Esterification of glycyrrhetinic acid (GA) with dehydrozingerone (DZ) resulted in a novel cytotoxic GA-DZ conjugate. Based on this exciting finding, we conjugated eleven different DZ analogs with GA or other triterpenoids, including oleanoic acid (OA) or Ursolic acid UA). In an in vitro anti-cancer assay using nine different human tumor cell lines, most of the GA-DZ conjugates showed significant potency. Particularly, compounds 5, 29, and 30 showed significant cytotoxic effects against LN-Cap, 1 A9, and KB cells with ED50 values of 0.6, 0.8, and 0.9 mu M, respectively. Similar conjugates between DZ and OA or UA were inactive suggesting that the GA component is critical for activity. Notably, although GA-DZ conjugates showed potent cytotoxic activity, the individual components (GA and DZ analogs) were inactive. Thus, GA-DZ conjugates are new chemical entities and represent interesting hits for anti-cancer drug discovery and development. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.027
• 作为产物：
  描述：

  3-氟-2-羟基苯甲醛 、 丙酮 在 sodium hydroxide 作用下， 以93%的产率得到4-(3-fluoro-2-hydroxy-phenyl)-but-3-en-2-one
  参考文献：
  名称：

  Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents

  摘要：

  Twenty-eight compounds related to dehydrozingerone ( 1), isoeugenol ( 3), and 2-hydroxychalcone ( 4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR ( a multidrug-resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 mu g/mL. Furthermore, dehydrozingerone analogue 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 mu g/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 mu g/mL, respectively) cells, suggesting that they are not substrates for the P-glycoprotein drug efflux pump.

  DOI：

  10.1021/np060252z

文献信息

• Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors
  作者：Bruce L. Finkelstein、Eric A. Benner、Maura C. Hendrixson、Kevin T. Kranis、James J. Rauh、Maya R. Sethuraman、Stephen F. McCann

  DOI：10.1016/s0968-0896(01)00326-1

  日期：2002.3

  Bridged-tricyclic cyanoguanidines 1 were found to be active as insecticides. The preparation and structure-activity relationships of oxacyclic (X=O) and carbocyclic (X=CH2) analogues of 1 is described. Compounds 1 were found to inhibit acetylcholinesterase with IC50 values comparable to the organophosphate Paraoxon. Unlike organophosphates. cyanoguanidines 1 were shown to reversibly bind acetylcholinesterase. This mode of action is shared by the structurally-related natural product Huperzine A. (C) 2002 Elsevier Science Ltd. All rights reserved.