(E)-1-Naphthalen-1-yl-3-[4-((E)-3-naphthalen-1-yl-3-oxo-propenyl)-phenyl]-propenone | 384807-29-8

• 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: (E)-1-Naphthalen-1-yl-3-[4-((E)-3-naphthalen-1-yl-3-oxo-propenyl)-phenyl]-propenone
• 英文别名: 3,3'-(1,4-Phenylene)bis[1-(naphthalen-1-yl)prop-2-en-1-one]；1-naphthalen-1-yl-3-[4-(3-naphthalen-1-yl-3-oxoprop-1-enyl)phenyl]prop-2-en-1-one
• CAS: 384807-29-8
• 化学式: C₃₂H₂₂O₂
• 分子量: 438.525
• InChiKey: FRJUSNJBEHTICZ-UHFFFAOYSA-N

物化性质

• 沸点：
  681.5±55.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-Naphthalen-1-yl-3-[4-((E)-3-naphthalen-1-yl-3-oxo-propenyl)-phenyl]-propenone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 1,4-bis(1-(4-(4-bromophenyl)thiazol-2-yl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-5-yl)benzene
  参考文献：
  名称：

  Synthesis and anticancer and cytotoxic effects of novel 1,4-phenylene-bis-N-thiocarbamoylpyrazole and 1,4-phenylene-bis-pyrazolylthiazole derivatives

  摘要：

  噻唑基吡唑啉衍生物最近被报导为有效的抗癌剂。在本研究中，合成了新型1,4-苯撑双-N-硫代氨基甲酰吡唑（3a-h）和1,4-苯撑双吡唑基噻唑（5a-h），并对其在C6（大鼠脑肿瘤细胞）和HeLa（人宫颈癌细胞）中的抗癌活性进行了筛选。抗癌活性研究作为剂量依赖性实验进行，从八种浓度开始。5-氟尿嘧啶（5-FU）作为阳性对照。化合物3c、3d和3h的试验结果显示，与5-FU在对C6细胞的选择性方面几乎具有相同的活性。此外，化合物3a-h的细胞毒性低于5-FU。尽管3a-h的低细胞毒性值以及其高抗增殖活性令人鼓舞，但还需要进一步研究这些分子作为抗癌药物的使用。

  DOI：

  10.3906/kim-1604-84
• 作为产物：
  描述：

  1-萘乙酮 、 对苯二甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (E)-1-Naphthalen-1-yl-3-[4-((E)-3-naphthalen-1-yl-3-oxo-propenyl)-phenyl]-propenone
  参考文献：
  名称：

  Synthesis and in vitro anticancer evaluation of 1,4-phenylene-bis-pyrimidine-2-amine derivatives

  摘要：

  在本研究中，通过邻苯二甲醛与取代芳基酮的反应合成了系列1,4-亚苯基双查尔酮3a-3h。在回流条件下，将盐酸胍加入到1,4-亚苯基双查尔酮3a-3h中，在乙醇钾溶液中得到了新型1,4-亚苯基双嘧啶-2-胺衍生物5a-5h。通过红外光谱、核磁共振（1H NMR和13C NMR）及元素分析解释了化合物的结构。对3a-3h和5a-5h的抗癌活性进行了研究，针对大鼠脑肿瘤细胞和人子宫颈癌在体外进行了活性测试，活性测试以剂量依赖性方式在八种浓度下进行。阳性对照为5-氟尿嘧啶（5-FU）。经过检测，化合物3c和3d显示出相较于5-FU对C6（大鼠脑肿瘤）和HeLa（人子宫颈癌）细胞的高活性。在高浓度下，5h对C6细胞的选择性抗癌活性优于5-FU。

  DOI：

  10.3906/kim-1603-112

文献信息

• Synthesis and anticancer activities of 1,4-phenylene-bis-N-acetyl- and N-phenylpyrazoline derivatives
  作者：Meliha Burcu Gürdere、Onur Gümüş、Ayse Sahin Yaglioglu、Yakup Budak、Mustafa Ceylan

  DOI：10.1007/s11164-016-2697-2

  日期：2017.3

  characterized by nuclear magnetic resonance (NMR) and infrared (IR) spectroscopic methods and elemental analysis. Compounds 3a–h and 4a–h were investigated to evaluate their anticancer activities against C6 (rat brain tumor cells) and HeLa (human uterus carcinoma) in vitro using a dose-dependent assay from 5 to 100 μM with 5-fluorouracil (5-FU) as standard anticancer drug. Compound 3a showed higher

  新型1,4-亚苯基-双-N-乙酰基（3a - h）和双-N-苯基吡唑啉衍生物（4a - h）是通过将水合肼和苯肼加入双查尔酮衍生物（1a - h）中获得的。乙酸和乙酸/乙醇分别在回流条件下反应4小时和8小时。用核磁共振（NMR）和红外（IR）光谱法及元素分析对所获得的双-N-乙酰基吡唑啉和双-N-苯基吡唑啉衍生物的结构进行表征。化合物3a – h和4a– h使用5-氟尿嘧啶（5-FU）作为标准抗癌药，以5至100μM的剂量依赖性试验研究了其在体外对C6（大鼠脑肿瘤细胞）和HeLa（人子宫癌）的抗癌活性。与5-FU相比，化合物3a显示出更高的针对HeLa细胞的细胞选择性活性。化合物3a – h（3d除外）对这两种细胞的活性均优于5-FU，特别是在高浓度下。与5-FU相比，化合物4c显示出更高的针对C6细胞的细胞选择性活性。化合物3a作为针对HeLa细胞的抗癌药物可能特别有前途。
• BF₃·OEt₂ catalyzed chemoselective CC bond cleavage of α,β-enones: an unexpected synthesis of 3-alkylated oxindoles and spiro-indolooxiranes
  作者：Sengodagounder Muthusamy、Ammasi Prabu

  DOI：10.1039/d1ob02002a

  日期：——

  of α,β-enones with diazoamides for the synthesis of 3-alkylated oxindoles is developed. Boron trifluoride etherate is found to be an effective catalyst for the chemoselective Cα–Cβ cleavage of enones to obtain 3-alkylated oxindoles. The product formation indicates a selective β-carbon elimination pathway of α,β-enones using the inexpensive BF3·OEt2 as a catalyst, transition metal-free conditions, an

  开发了一种BF 3 ·OEt 2催化的α,β-烯酮与重氮酰胺的高化学选择性形式C C双键裂解反应，用于合成3-烷基化羟吲哚类化合物。发现三氟化硼醚合物是化学选择性 C α -C β裂解烯酮以获得 3-烷基化羟吲哚的有效催化剂。产物的形成表明以廉价的BF 3 ·OEt 2为催化剂， α,β-烯酮的选择性β-碳消除途径，无过渡金属条件，露天环境，良好的功能耐受性和广泛的底物范围。该协议的合成效用通过合成螺吲哚环氧乙烷来突出。
• A FACILE SYNTHESIS OF 1,4-<i>BIS-</i>(3-ARYL-3-OXO-1-PROPENYL)BENZENES UNDER MICROWAVE IRRADIATION
  作者：Jian-Feng Zhou、Jun-Feng Zhou、Zheng-Cai Zou、Jun-Cai Feng

  DOI：10.1081/scc-120014048

  日期：2002.1

  1,4-bis(3-Aryl-3-oxo-1-propenyl) benzenes were synthesized by 1,4-benzenedicarboxaldehyde with substituted acetophenones in the presence of sodium hydroxide under microwave irradiation with good yields.
• Synthesis and in vitro anticancer evaluation of 1,4-phenylene-bis-pyrimidine-2-amine derivatives
  作者：Meliha Burcu GÜRDERE、Erdoğan KAMO、Ayşe ŞAHİN YAĞLIOĞLU、Yakup BUDAK、Mustafa CEYLAN

  DOI：10.3906/kim-1603-112

  日期：——

  A series of 1,4-phenylene-bis-chalcones 3a-3h were synthesized by the reaction of terephthalaldehyde with substituted arylketones in this study. The novel 1,4-phenylene-bis-pyrimidine-2-amine derivatives 5a-5h were obtained by the addition of guanidine hydrochloride to 1,4-phenylene-bis-chalcone 3a-3h in ethanolic KOH under reflux conditions. The structure of the compounds was explained by means of IR, $^1}$H NMR, $^13}$C NMR, and elemental analyses. The anticancer activities of 3a-3h and 5a-5h were investigated against rat brain tumor cells and human uterus carcinoma in vitro$.$ Activity tests were performed as dose-dependent assays at eight concentrations. The positive control was 5-fluorouracil (5-FU). Compounds 3c and 3d were examined and they showed high activities as compared to 5-FU against C6 (rat brain tumor) and HeLa (human uterus carcinoma) cells. The anticancer activity of 5h was better than that of 5-FU at high concentrations cell-selectively against C6 cells.

  在本研究中，通过邻苯二甲醛与取代芳基酮的反应合成了系列1,4-亚苯基双查尔酮3a-3h。在回流条件下，将盐酸胍加入到1,4-亚苯基双查尔酮3a-3h中，在乙醇钾溶液中得到了新型1,4-亚苯基双嘧啶-2-胺衍生物5a-5h。通过红外光谱、核磁共振（1H NMR和13C NMR）及元素分析解释了化合物的结构。对3a-3h和5a-5h的抗癌活性进行了研究，针对大鼠脑肿瘤细胞和人子宫颈癌在体外进行了活性测试，活性测试以剂量依赖性方式在八种浓度下进行。阳性对照为5-氟尿嘧啶（5-FU）。经过检测，化合物3c和3d显示出相较于5-FU对C6（大鼠脑肿瘤）和HeLa（人子宫颈癌）细胞的高活性。在高浓度下，5h对C6细胞的选择性抗癌活性优于5-FU。
• Synthesis and anticancer and cytotoxic effects of novel 1,4-phenylene-bis-N-thiocarbamoylpyrazole and 1,4-phenylene-bis-pyrazolylthiazole derivatives
  作者：Meliha Burcu GÜRDERE、Erdoğan KAMO、Yakup BUDAK、Ayşe ŞAHİN YAĞLIOĞLU、Mustafa CEYLAN

  DOI：10.3906/kim-1604-84

  日期：——

  Thiazolylpyrazoline derivatives were recently reported as potent anticancer agents. In this study, novel 1,4-phenylene-bis-N-thiocarbamoylpyrazoles (3a-h and 1,4-phenylene-bis-pyrazolylthiazoles (5a-h were prepared and screened for their anticancer activities against C6 (rat brain tumor cells) and HeLa (human uterus carcinoma). Anticancer activity studies were performed as a dose-dependent assay starting with eight concentrations. 5-Fluorouracil (5-FU) was used as a positive control. Compounds 3c, 3d, and 3h were examined and they revealed almost the same activities compared with 5-FU in terms of cell selectivity against C6 cells. Moreover, compounds 3a-h had lower cytotoxicity than 5-FU. The low cytotoxicity values of 3a-h as well as their high antiproliferative activity were encouraging, but further studies are required on the use of these molecules as anticancer drugs.

  噻唑基吡唑啉衍生物最近被报导为有效的抗癌剂。在本研究中，合成了新型1,4-苯撑双-N-硫代氨基甲酰吡唑（3a-h）和1,4-苯撑双吡唑基噻唑（5a-h），并对其在C6（大鼠脑肿瘤细胞）和HeLa（人宫颈癌细胞）中的抗癌活性进行了筛选。抗癌活性研究作为剂量依赖性实验进行，从八种浓度开始。5-氟尿嘧啶（5-FU）作为阳性对照。化合物3c、3d和3h的试验结果显示，与5-FU在对C6细胞的选择性方面几乎具有相同的活性。此外，化合物3a-h的细胞毒性低于5-FU。尽管3a-h的低细胞毒性值以及其高抗增殖活性令人鼓舞，但还需要进一步研究这些分子作为抗癌药物的使用。