1,5-bis(2-naphthyl)-1,4-pentadien-3-one | 41662-78-6

• 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
• 英文名称: 1,5-bis(2-naphthyl)-1,4-pentadien-3-one
• 英文别名: 1,5-di(naphthalen-2-yl)penta-1,4-dien-3-one；1,5-di-[2]naphthyl-penta-1,4-dien-3-one；β.β'-Di-β-naphthyl-divinyl-keton；1.5-Di-β-naphthyl-pentadien-(1.4)-on-(3)；α.α'-Bis-β-naphthylmethylen-aceton；1,5-Di-[2]naphthyl-penta-1,4-dien-3-on；1,5-dinaphthalen-2-ylpenta-1,4-dien-3-one
• CAS: 41662-78-6
• 化学式: C₂₅H₁₈O
• 分子量: 334.417
• InChiKey: CKKPHXZAMHRIFO-UHFFFAOYSA-N

物化性质

• 沸点：
  569.0±39.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• 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：
  1

反应信息

• 作为反应物：
  描述：

  1,5-bis(2-naphthyl)-1,4-pentadien-3-one 在 溶剂黄146 、 锌 作用下， 生成 1,5-bis(2-naphthyl)-3-pentanone
  参考文献：
  名称：

  Time-resolved observation of excitation hopping between two identical chromophores attached to both ends of alkanes

  摘要：

  DOI：

  10.1021/ja00233a004
• 作为产物：
  描述：

  N-苯基萘-2-甲酰胺 在 五氯化磷 、 sodium methylate 、 1,1,2,2-四氯乙烷 作用下， 生成 1,5-bis(2-naphthyl)-1,4-pentadien-3-one
  参考文献：
  名称：

  Gibson et al., Journal of the Chemical Society, 1926, p. 2253

  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。
• Base-catalyzed cross coupling of secondary alcohols and aryl-aldehydes with concomitant oxidation of alcohols to ketones: An alternative route for synthesis of the Claisen-Schmidt condensation products
  作者：Naveen Satrawala、Kamal N. Sharma、Leah C. Matsinha、Latisa Maqeda、Shepherd Siangwata、Gregory S. Smith、Raj K. Joshi

  DOI：10.1016/j.tetlet.2017.05.093

  日期：2017.7

  alkanones was obtained in moderate to good yields using various secondary alcohols and substituted aryl-aldehydes. Herein, α,α′-bis-(benzylidene)alkanones, which are the classical products of Claisen-Schmidt (cross aldol) condensation, have been synthesized via an alternative strategy using secondary alcohols. Bis-(benzylidene) alkanones are an integral part of various drug regimes and the production of bis-(benzylidene)

  当在催化量（20摩尔％）的K 2 CO存在下，将芳基醛的醇溶液回流搅拌45小时时，实现了碱催化的仲醇与芳基醛的CC交叉偶联3。使用各种仲醇和取代的芳基醛，可以以中等至良好的收率获得一致形成的α，α'-双-（亚苄基）链烷酮。在此，已经通过使用仲醇的替代策略合成了作为克莱森-施密特（十字醇醛）缩合的经典产物的α，α′-双-（亚苄基）链烷酮。双-（亚苄基）链烷酮是各种药物方案和双酚生产中必不可少的部分不使用任何贵金属的-（亚苄基）链烷酮是本反应的主要结果。
• 不对称双共轭加成合成光学活性酮类化合物的方法
  申请人：河南师范大学

  公开号：CN112811996B

  公开（公告）日：2023-01-03

  本发明公开了不对称双共轭加成合成光学活性酮类化合物的方法，属于有机化学中的不对称合成技术领域。具体步骤如下：以二烯酮1和有机硼酸2为原料，在手性联二萘酚或手性四苯并环辛四烯类催化剂和分子筛存在下，经过不对称共轭加成反应得到酮类化合物3。反应方程式如下：本发明的优势在于：反应原料易得，催化剂结构简单，催化效率高，反应条件温和，后处理简单。
• 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