Terephthalbis(p-chloroacetophenone) | 26473-69-8

• 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: Terephthalbis(p-chloroacetophenone)
• 英文别名: 1,4-Di-(4'-chlorbenzoylvinyl)-benzol；1-(4-Chlorophenyl)-3-[4-[3-(4-chlorophenyl)-3-oxoprop-1-enyl]phenyl]prop-2-en-1-one
• CAS: 26473-69-8
• 化学式: C₂₄H₁₆Cl₂O₂
• 分子量: 407.296
• InChiKey: IWUOYBOYNSPSDX-UHFFFAOYSA-N

物化性质

• 熔点：
  250-252 °C
• 沸点：
  599.8±50.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• 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：

  Terephthalbis(p-chloroacetophenone) 在 一水合肼 作用下， 以 乙醇 为溶剂， 以87%的产率得到3-(4-chlorophenyl)-5-[4-[3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-5-yl]phenyl]-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  杂环。7.合成新的吡唑啉

  摘要：

  DOI：

  10.1021/je00042a042
• 作为产物：
  描述：

  对苯二甲醛 、 对氯苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 Terephthalbis(p-chloroacetophenone)
  参考文献：
  名称：

  氯化铝催化吡咯和吲哚与查耳酮和双查耳酮衍生物的 C-烷基化

  摘要：

  摘要 AlCl3 催化吡咯 (2) 与查耳酮 (1a-i) 以 8:1 的比例在 10 mol% AlCl3 存在下烷基化，在室温下得到单独的 2-烷基吡咯 (3a-i) 12收益良好。使用比例为 1:3 的吡咯 (2) 和查耳酮在 CH3CN 中在室温下进行相同的反应 3 小时，以获得 2,5-二烷基吡咯 (4a-f)。此外，吡咯 (2) 和吲哚 (7) 在 1,4-亚苯基双查耳酮 (5a-g) 上以 8:1 的比例在室温下反应 24 小时，得到双加成产物 6a- g 和 8a-g 分别具有良好的产量。产物的结构经1H和13C核磁共振谱和元素分析证实。图形概要

  DOI：

  10.1080/00397911.2015.1136644

文献信息

• 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。
• ‘One-pot’ ultrasound irradiation promoted synthesis and spectral characterization of an array of novel 1,1′-(5,5′-(1,4-phenylene)bis(3-aryl-1H-pyrazole-5,1(4H,5H)-diyl))diethanones, a bis acetylated pyrazoles derivatives
  作者：V. Kanagarajan、M.R. Ezhilarasi、M. Gopalakrishnan

  DOI：10.1016/j.saa.2010.11.038

  日期：2011.2

  An array of novel 1,1'-(5,5'-(1,4-phenylene)bis(3-aryl-1H-pyrazole-5,1(4H,5H)-diyl))diethanones, a bis acetylated pyrazoles derivatives are synthesized in 'one-pot' by ultrasound irradiation method and are characterized by melting point, elemental analysis, MS, FT-IR, one-dimensional NMR (1H and 13C) and two-dimensional NOESY spectra. The methylene and methane protons of pyrazoles moiety splits signal

  一系列新型1,1'-（5,5'-（1,4-亚苯基）双（3-芳基-1H-吡唑-5,1（4H，5H）-二基））二酮，双乙酰化吡唑衍生物通过超声辐射法在“一锅法”中合成，并通过熔点，元素分析，MS，FT-IR，一维NMR（1H和13C）和二维NOESY光谱进行表征。吡唑部分的亚甲基和甲烷质子在质子NMR光谱中以ABX模式分裂信号，NOESY光谱证实了关键的nOe相关性。
• Study of 1,3-Dipolar Cycloaddition and Ring Contraction of New 1,4-Phenylene-bis[1,5]benzothiazepine Derivatives
  作者：Fei Chen、Fang-Ming Liu、Zhi-Qiang Dong

  DOI：10.1002/jhet.1880

  日期：2014.11

  Some 1,4‐phenylene‐bis[1,2,4]oxadiazolo‐[5,4‐d][1,5]benzothiazepine derivatives (4a, 4b, 4c) were synthesized by 1,3‐dipolar cycloaddition reaction of benzohydroximinoyl chloride with 1,4‐phenylene‐bis(4‐aryl)‐2,3‐dihydro[1,5]benzothiazepine (2a, 2b, 2c); meanwhile, compounds 2a, 2b, 2c also occurred ring contraction under acylating condition to obtain bis[2‐aryl‐2′‐(β‐1,4‐phenylenevinyl)‐3‐acetyl]‐2

  通过苯并氢氧杂氨基的1,3-偶极环加成反应合成了一些1,4-亚苯基-双[1,2,4]恶二唑并[5,4- d ] [1,5]苯并噻氮平衍生物（4a，4b，4c）氯化物与1,4-亚苯基-双（4-芳基）-2,3-二氢[1,5]苯并硫氮杂（（2a，2b，2c）; 同时，化合物2a，2b，2c在酰化条件下也发生环收缩，从而获得双[2-芳基-2'-（β-1,4-亚苯基乙烯基）-3-乙酰基] -2,3-二氢[1,5 ]苯并噻唑（3a，3b，3c）。红外光谱证实了一些新型化合物的结构，1 H-NMR，元素和X射线晶体学分析。
• ZnO Nanoparticles Catalyst in the Synthesis of Bioactive Fused Pyrimidines as Anti-breast Cancer Agents Targeting VEGFR-2
  作者：Dina H. Dawood、Eman M.H. Abbas、Thoraya A. Farghaly、Mamdouh M. Ali、Mohammed F. Ibrahim

  DOI：10.2174/1573406414666180912113226

  日期：2019.4.12

  of newly fused pyrimidine derivatives against breast MCF-7 cancer was performed. It was apparent that the 2-phenylpyrazolo[1,5-a]pyrimidine derivatives 9a (IC50 = 9.12±1.16 µg/ml), 9c (IC50 = 9.10±1.07 µg/ml) and 9d (IC50 = 9.60±1.22 µg/ml) exhibited equipotent antitumor activity as Tamoxifen (IC50 = 9.11±0.90 µg/ml). Also, the inhibitory activity of the novel fused pyrimidine derivatives on VEGFR-2

  背景：嘧啶类化合物是一类杰出的杂环化合物，它通过各种生物活性抗肿瘤剂增强了药物化学作用。此外，嘧啶支架显示出VEGFR-2抑制活性。而且，在有机反应中使用纳米级催化剂以加速催化过程。 目的：我们感兴趣的是使用ZnO（NPs）合成一系列新的融合嘧啶，以研究其对乳腺癌MCF7的抗肿瘤作用及其VEGFR-2抑制特性。 方法：使用氧化锌纳米颗粒ZnO（NPs）在回流的乙醇中开发了一种简单而有效的合成稠合嘧啶的方法。 结果：所有新的稠合嘧啶的拟议结构与其光谱数据相符。进行了新融合的嘧啶衍生物对乳腺癌MCF-7癌症的抗肿瘤评估。显然，2-苯基吡唑并[1,5-a]嘧啶衍生物9a（IC50 = 9.12±1.16 µg / ml），9c（IC50 = 9.10±1.07 µg / ml）和9d（IC50 = 9.60±1.22 µg / ml）毫升）表现出等效的抗肿瘤活性，如他莫昔芬（IC50 = 9.11±0
• 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。