1,5-二(3-硝基苯基)戊-1,4-二烯-3-酮 | 621-21-6

• 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
• 中文名称: 1,5-二(3-硝基苯基)戊-1,4-二烯-3-酮
• 英文名称: 1,5-bis-(3-nitro-phenyl)-penta-1,4-dien-3-one
• 英文别名: 1,5-Bis-(3-nitro-phenyl)-penta-1,4-dien-3-on；3.3'-Dinitro-dibenzylidenaceton；Bis-(3-nitro-benzyliden)-aceton；3.3'-Dinitro-distyrylketon；3.3'-Dinitro-dibenzalaceton；Bis-(3-nitro-benzal)-aceton；1,5-Bis(3-nitrophenyl)-1,4-pentadien-3-one；1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one
• CAS: 621-21-6
• 化学式: C₁₇H₁₂N₂O₅
• mdl: MFCD00498489
• 分子量: 324.293
• InChiKey: ZPQURSDVJWZXLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  237 °C
• 沸点：
  533.8±50.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  1,5-二(3-硝基苯基)戊-1,4-二烯-3-酮 在 镍 盐酸 、 硫酸 、 氢气 、 肼 作用下， 反应 2.0h， 生成 3,3'-Hydrazo-bis-<3-cyan-1,5-bis-(3-benzolazo-phenyl)-pentan>
  参考文献：
  名称：

  Die Herstellung azobenzolgruppenhaltiger ?, ??-Azo-[isobutters�ure-nitril]-derivate und ihre Anwendung zur Polymerisation

  摘要：

  DOI：

  10.1007/bf00900158
• 作为产物：
  描述：

  4-(3-nitrophenyl)but-3-en-2-one 在 氢氧化钾 作用下， 生成 1,5-二(3-硝基苯基)戊-1,4-二烯-3-酮
  参考文献：
  名称：

  van der Lee, Recueil des Travaux Chimiques des Pays-Bas, 1928, vol. 47, p. 930

  摘要：

  DOI：

文献信息

• BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER
  申请人：Shibata Hiroyuki

  公开号：US20100152493A1

  公开（公告）日：2010-06-17

  It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

  要改善姜黄素的溶解度，以开发一种能够在低浓度下抑制各种癌细胞生长的抗肿瘤化合物。因此，披露了一种新型合成化合物，双(芳基甲基亚乙酮)，具有优异的抗肿瘤活性和化学预防活性。合成并筛选了一种双(芳基甲基亚乙酮)（即具有姜黄素骨架的衍生物），它是一种抗肿瘤化合物并具有化学预防活性。可以合成具有增强抗肿瘤活性和化学预防活性的衍生物。
• Sulfamic acid: An efficient, cost-effective and green catalyst for crossed-aldol condensation of ketones with aromatic aldehydes under solvent-free
  作者：Amin Rostami、Firoz Ahmad-Jangi

  DOI：10.1016/j.cclet.2011.03.015

  日期：2011.9

  Abstract Aromatic aldehydes undergo crossed-aldol condensation with ketones in the presence of catalytic amount of sulfamic acid (SA) to afford the corresponding α , β -unsaturated aldol products under solvent-free conditions in good to high yields at 45–80 °C.

  摘要在催化量的氨基磺酸（SA）存在下，芳香醛与酮进行了交叉羟醛缩合反应，在无溶剂条件下，在45–80°C的条件下，能以高至高收率得到相应的α，β-不饱和羟醛产品。
• Synthesis of Pyridine-Dicarboxamide-Cyclohexanone Derivatives: Anticancer and α-Glucosidase Inhibitory Activities and In Silico Study
  作者：Abdullah Al-Majid、Mohammad Islam、Saleh Atef、Fardous El-Senduny、Farid Badria、Yaseen Elshaier、M. Ali、Assem Barakat、A. Motiur Rahman

  DOI：10.3390/molecules24071332

  日期：——

  An efficient and practical method for the synthesis of 2,6-diaryl-4-oxo-N,N′-di(pyridin-2-yl)cyclohexane-1,1-dicarboxamide is described in this present study, which occurs through a double Michael addition reaction between diamide and various dibenzalacetones. The reaction was carried out in dichloromethane (DCM) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The anticancer activities of the synthesized compounds were evaluated in several cancer cell lines, including MCF-7, MDA-MB-231, SAS, PC-3, HCT-116, HuH-7 and HepG2 cells. From these experiments, we determined that MDA-MB-231 was the most sensitive cancer cell line to the compounds 3c, 3e, 3d, 3j and 3l, which exhibited variable anticancer activities (3l [IC50 = 5 ± 0.25 µM] > 3e [IC50 = 5 ± 0.5 µM] > 3c [IC50 = 7 ± 1.12 µM] > 3d [IC50 = 18 ± 0.87 µM] > 3j [IC50 = 45 ± 3 µM]). Of these, 3l (substituted p-trifluoromethylphenyl and chloropyridine) showed good potency (IC50 = 6 ± 0.78 µM) against HCT-116 colorectal cancer cells and exhibited high toxicity against HuH-7 liver cancer cells (IC50 = 4.5 ± 0.3 µM). These values were three times higher than the values reported for cisplatin (IC50 of 8 ± 0.76 and 14.7 ± 0.5 µM against HCT-116 and HuH-7 cells, respectively). The highest α-glucosidase inhibitory activity was detected for the 3d, 3i and 3j compounds. The details of the binding mode of the active compounds were clarified by molecular docking studies.

  本研究描述了一种高效实用的方法，用于合成2,6-二芳基-4-氧代-N,N′-二(吡啶-2-基)环己烷-1,1-二甲酰胺，该方法通过二酰胺与各种二苯乙酮之间的双Michael加成反应实现。反应在二氯甲烷（DCM）中，在1,8-二氮杂双环[5.4.0]十一烯（DBU）存在下进行。评估了合成化合物在几种癌细胞系中的抗癌活性，包括MCF-7、MDA-MB-231、SAS、PC-3、HCT-116、HuH-7和HepG2细胞。从这些实验中，我们确定MDA-MB-231对化合物3c、3e、3d、3j和3l表现出最敏感的抗癌活性，这些化合物表现出不同的抗癌活性（3l [IC50 = 5 ± 0.25 µM] > 3e [IC50 = 5 ± 0.5 µM] > 3c [IC50 = 7 ± 1.12 µM] > 3d [IC50 = 18 ± 0.87 µM] > 3j [IC50 = 45 ± 3 µM]）。其中，3l（取代p-三氟甲基苯基和氯吡啶）对HCT-116结肠癌细胞显示出良好的效力（IC50 = 6 ± 0.78 µM），并对HuH-7肝癌细胞表现出高毒性（IC50 = 4.5 ± 0.3 µM）。这些值比顺铂报告的值高三倍（分别为HCT-116和HuH-7细胞的IC50分别为8 ± 0.76和14.7 ± 0.5 µM）。化合物3d、3i和3j显示出最高的α-葡萄糖苷酶抑制活性。通过分子对接研究澄清了活性化合物的结合模式细节。
• Synthesis, in vitro biological activities and in silico study of dihydropyrimidines derivatives
  作者：Assem Barakat、Mohammad Shahidul Islam、Abdullah Mohammed Al-Majid、Hazem A. Ghabbour、Hoong-Kun Fun、Kulsoom Javed、Rehan Imad、Sammer Yousuf、M. Iqbal Choudhary、Abdul Wadood

  DOI：10.1016/j.bmc.2015.09.001

  日期：2015.10

  evaluated for their in vitro cytotoxic activity against PC-3, HeLa, and MCF-3 cancer cell lines, and 3T3 mouse fibroblast cell line. All compounds were found to be non cytotoxic, except compounds 3f and 3m (IC50=17.79±0.66-20.44±0.30 μM), which showed a weak cytotoxic activity against the HeLa, and 3T3 cell lines. In molecular docking simulation study, all the compounds were docked into the active site

  我们在这里描述了二氢嘧啶衍生物3a-p的合成及其α-葡萄糖苷酶抑制活性的评估。化合物3b（IC50 = 62.4±1.5μM），3c（IC50 = 25.3±1.26μM），3d（IC50 = 12.4±0.15μM），3e（IC50 = 22.9±0.25μM），3g（IC50 = 23.8±0.17μM） ，3h（IC50 = 163.3±5.1μM），3i（IC50 = 30.6±0.6μM），3m（IC50 = 26.4±0.34μM）和3o（IC50 = 136.1±6.63μM）被发现是有效的α-葡萄糖苷酶抑制剂。与标准药物阿卡波糖（IC50 = 840±1.73μM）相比。还评估了这些化合物对PC-3，HeLa和MCF-3癌细胞系以及3T3小鼠成纤维细胞系的体外细胞毒活性。除化合物3f和3m（IC50 = 17.79±0.66-20.44±0.30μM）（对HeLa和3T3细
• Petrenko-Kritschenko, Chemische Berichte, 1898, vol. 31, p. 1512
  作者：Petrenko-Kritschenko

  DOI：——

  日期：——