(2E)-1-(2-naphthyl)-3-(4-fluorophenyl)-2-propen-1-one | 104765-79-9

• 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: (2E)-1-(2-naphthyl)-3-(4-fluorophenyl)-2-propen-1-one
• 英文别名: 3t-(4-fluoro-phenyl)-1-[2]naphthyl-propenone；3t-(4-Fluor-phenyl)-1-[2]naphthyl-propenon；3-(4-Fluorophenyl)-1-(2-naphthyl)prop-2-en-1-one；(E)-3-(4-fluorophenyl)-1-naphthalen-2-ylprop-2-en-1-one
• CAS: 104765-79-9
• 化学式: C₁₉H₁₃FO
• 分子量: 276.31
• InChiKey: BCVIZJTYUVWPOB-KPKJPENVSA-N

物化性质

• 沸点：
  439.6±37.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-1-(2-naphthyl)-3-(4-fluorophenyl)-2-propen-1-one 在 sodium ethanolate 、 sodium acetate 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 4-(4-fluorophenyl)-4,5-dihydro-6-(naphthalen-2-yl)-2H-indazol-3-ol
  参考文献：
  名称：

  Synthesis, spectral analysis and in vitro microbiological evaluation of novel ethyl 4-(naphthalen-2-yl)-2-oxo-6-arylcyclohex-3-enecarboxylates and 4,5-dihydro-6-(napthalen-2-yl)-4-aryl-2H-indazol-3-ols

  摘要：

  A series of ethyl 4-(naphthalen-2-yl)-2-oxo-6-arylcyclohex-3-enecarboxylates 8--14 and 4,5-dihydro-6-(naphthalen-2-yl)-4-aryl-2H-indazol-3-ols 15--21 were synthesised and characterised by their spectroscopic data. In vitro microbiological evaluations were carried out for all the newly synthesised compounds 8--21 against clinically isolated bacterial and fungal strains. Compounds 9, 12 and 20 against Staphylococcus aureus, 10, 12, 20 against beta beta-haemolytic streptococcus, 11, 17 against Bacillus subtilis, 12, 16 and 20 against Vibreo cholerae, 13, 16 against Escherichia coli, 13, 16, 18, 19 against Salmonella typhii, 12, 18 against Shigella flexneri, 10 against Salmonella typhii, 10, 13, 17, 18 against Aspergillus flavus, 12, 17, 21 against Aspergillus niger, 12, 15, 17, 18, 20 against Mucor, Rhizopus and Microsporeum gypsuem exhibit potent antimicrobial activity.

  DOI：

  10.3109/14756361003689856
• 作为产物：
  描述：

  对氟苯甲醛 、 2-萘乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (2E)-1-(2-naphthyl)-3-(4-fluorophenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis, in vitro and in silico Studies of Naphthalene Pyrazoline Prop-2-en-1-one Derivatives

  摘要：

  合成的新萘吡唑丙烯酮衍生物（NDPP 1-8）是通过乙酸乙酯、水合肼与NPD的Michael加成反应得到的，NPD作为多组分支架。 （E）-1-（萘-3-基）-3-苯基丙烯酮（NPD）是通过2-乙酰基萘和取代醛经过Claisen-Schmidt缩合反应形成的。 通过红外、1H和13C NMR光谱数据以及元素分析确认了NDPP骨架结构。 NDPP化合物的结构经过了分子对接和ADME研究。 ADME预测结果显示，含有电子吸引性-Cl基团的化合物NDPP 2具有较高的药物相似性值4.21，而含有电子供体CH3和OCH3基团的化合物NDPP 4和7显示的药物相似性值为2.62。 NDPP 2的药物评分也较高，为0.63，而NDPP 4和NDPP 7的药物评分分别为0.60和0.69。 对接研究表明，含有电子吸引性NO2基团的化合物NDPP 5与1UAG蛋白对接具有良好的结合亲和力值-8.8Kcal/mol。 这些化合物显示出良好的药物相似性值2.25和药物评分0.65。 体外研究显示具有相同NO2取代衍生物的高抑制值。 所有化合物的结合亲和力值均高于标准结合亲和力值。

  DOI：

  10.14233/ajchem.2020.22654

文献信息

• Synthesis of fluoro derivatives of 2,4,6-triarylpyridines
  作者：R.S. Tewari、Anita Bajpai

  DOI：10.1016/s0022-1139(00)80543-6

  日期：1985.7

  A variety of fluoro-substituted 2,4,6-triarylpyridines have been prepared via the reaction of 4-picolinium 4-chlorophenacyl methylide, with a series of fluorinated α,β-unsaturated ketones in the presence of ammonium acetate in acetic acid.

  在乙酸铵存在下，通过4-吡啶甲基4-氯苯甲酰基甲基与一系列氟化的α，β-不饱和酮的反应，已经制备了多种氟取代的2,4,6-三芳基吡啶。
• New Fluorine-containing Aromatics as Potential Carcinostats
  作者：NG. PH. BUU-HOÏ、N. D. XUONG、R. RIPS

  DOI：10.1021/jo01353a028

  日期：1957.2
• Buu-Hoi; Sy, Bulletin de la Societe Chimique de France, 1958, p. 219
  作者：Buu-Hoi、Sy

  DOI：——

  日期：——
• Naphthylchalcones induce apoptosis and caspase activation in a leukemia cell line: The relationship between mitochondrial damage, oxidative stress, and cell death
  作者：Evelyn Winter、Louise Domeneghini Chiaradia、Clarissa A.S. de Cordova、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.bmc.2010.09.025

  日期：2010.11

  In this study, we investigated the effects of 24 chalcone derivatives from 2-naphthylacetophenone toward a lymphoblastic leukemia cell line (L1210). Three compounds, called R7, R13, and R15, presented concentration- and time-dependent cytotoxicity and induced cellular death by apoptosis via mitochondrial injury and oxidative stress. The effects of these compounds appear to occur through different mechanisms because R13 and R7 induced a greater disturbance of mitochondrial potential, and all compounds induced disturbances of cellular ATP content and increased caspase-3 activity before cellular death. These compounds also interfered with antioxidant enzymes activities and GSH content through different mechanisms. (C) 2010 Elsevier Ltd. All rights reserved.
• Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi
  作者：Deise M. Borchhardt、Alessandra Mascarello、Louise Domeneghini Chiaradia、Ricardo J. Nunes、Glaucius Oliva、Rosendo A. Yunes、Adriano D. Andricopulo

  DOI：10.1590/s0103-50532010000100021

  日期：——

  Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 mu M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.