(1E,4E)-1,5-bis(2-bromophenyl)penta-1,4-dien-3-one | 114657-35-1

• 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: (1E,4E)-1,5-bis(2-bromophenyl)penta-1,4-dien-3-one
• CAS: 114657-35-1
• 化学式: C₁₇H₁₂Br₂O
• 分子量: 392.09
• InChiKey: USWOVAGRUBOXNT-WGDLNXRISA-N

物化性质

• 熔点：
  145 °C
• 沸点：
  487.7±40.0 °C(Predicted)
• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1,5-bis(2-bromophenyl)penta-1,4-dien-3-one 在 potassium fluoride 、 四(三苯基膦)钯 、 三正丁基氢锡 、 palladium diacetate 、 copper (I) acetate 、 溶剂黄146 、 三苯基膦 作用下， 以 1,4-二氧六环 、 吡啶 、 乙醚 、 三乙胺 、 N,N-二甲基甲酰胺 、 xylene 、 苯 为溶剂， 反应 14.83h， 生成 13,14,16,17-tetrahydro-5,6,7,8-tetradehydrodibenzocyclotridecen-15-one
  参考文献：
  名称：

  Acheson, R. Morrin; Lee, Gary C. M., Journal of the Chemical Society. Perkin transactions I, 1987, p. 2321 - 2332

  摘要：

  DOI：
• 作为产物：
  描述：

  丙酮 、 邻溴苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以31%的产率得到(1E,4E)-1,5-bis(2-bromophenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  通过连续[4 + 2]环加成反应向六氢2 H-苯甲基机械激发的途径

  摘要：

  利用两个健壮的C-C键形成反应中，的Baylis-Hillman反应和狄尔斯-阿尔德反应，我们报告六氢- 2的高度对映选择性，区域选择性和立体选择性合成ħ通过两个连续的[4 + 2 -chromenes ]环加成。这些串联和形式环加成反应也已作为“一锅”序列进行，以优异的收率和立体选择性进入构成多达五个连续立体中心的相应杂环。

  DOI：

  10.1021/acs.orglett.6b01742

文献信息

• Synthesis and Anti-bacterial Properties of Mono-carbonyl Analogues of Curcumin
  作者：Guang Liang、Shulin Yang、Lijuan Jiang、Yu Zhao、Lili Shao、Jian Xiao、Faqing Ye、Yueru Li、Xiaokun Li

  DOI：10.1248/cpb.56.162

  日期：——

  The synthesis of three series of curcumin analogues with mono-carbonyl is described. Their in vitro anti-bacterial activities against seven Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the aryl ring and the space structure of the linking strain were discussed. It was observed that part of the derivatives displayed significant activity when compared with curcumin and most of them exhibited activity against the ampicillin-resisted Enterobacter cloacae. Compounds A12, B09, B13, B14 and C09 show remarkable antibacterial activity in vitro. The result showed that heterocycle or long-chain substituents may enhance the activity of curcumin analogues.

  本文描述了三种单羰基姜黄素类似物的合成。对七种革兰氏阳性和革兰氏阴性细菌进行了体外抗菌活性测试，并讨论了取代基对芳环和连接张力的空间结构的影响。观察到，与姜黄素相比，部分衍生物显示出显著的活性，并且大多数衍生物对氨苄西林抵抗的阴沟肠杆菌表现出活性。化合物A12、B09、B13、B14和C09显示出显著的体外抗菌活性。结果显示，杂环或长链取代基可能增强姜黄素类似物的活性。
• Synthesis of tetracyclic oxindoles and evaluation of their α-glucosidase inhibitory and glucose consumption-promoting activity
  作者：Lei Hao、Yujiao Ma、Lianbo Zhao、Yinan Zhang、Xinying Zhang、Ying Ma、Robert H. Dodd、Hua Sun、Peng Yu

  DOI：10.1016/j.bmcl.2020.127264

  日期：2020.7

  These compounds were evaluated for α-glucosidase inhibitory and glucose consumption-promoting activity in vitro. Compound 4l competitively and reversibly inhibited α-glucosidase (IC50 = 3.64 μM) with activity 14–fold higher than that of acarbose. Docking analysis substantiated these findings. In addition, compound 4l exhibited significant glucose consumption promoting activity at 1 μM.

  通过不对称的1、3-偶极反应分2-4个步骤合成了一系列四环羟吲哚衍生物，总产率为57-86％。评价了这些化合物在体外的α-葡萄糖苷酶抑制作用和促进葡萄糖消耗的活性。化合物4l具有竞争性和可逆性地抑制α-葡萄糖苷酶（IC 50 = 3.64μM），其活性比阿卡波糖高14倍。对接分析证实了这些发现。另外，化合物4l在1μM处表现出显着的促进葡萄糖消耗的活性。
• Monocarbonyl Analogs of Curcumin with Potential to Treat Colorectal Cancer
  作者：Marta Clariano、Vanda Marques、João Vaz、Salma Awam、Marta B. Afonso、Maria Jesus Perry、Cecília MP Rodrigues

  DOI：10.1002/cbdv.202300222

  日期：2023.3

  small library of monocarbonyl analogs of curcumin 1a–q was synthesized. Lipophilicity and stability in physiological conditions were both assessed by HPLC-UV, while two different methods assessed the electrophilic character of each compound monitored by NMR and by UV-spectroscopy. The potential therapeutic effect of the analogs 1a–q was evaluated in human colon carcinoma cells and toxicity in immortalized

  姜黄素具有多种生物学特性，使得这种化合物可以有效治疗包括癌症在内的多种疾病。然而，姜黄素的临床应用因其较差的药代动力学而受到影响，因此寻找具有更好药代动力学和药理学特性的新型类似物至关重要。在这里，我们的目的是评估姜黄素单羰基类似物的稳定性、生物利用度和药代动力学特征。合成了姜黄素1a–q的单羰基类似物的小型文库。生理条件下的亲脂性和稳定性均通过 HPLC-UV 进行评估，同时通过 NMR 和 UV 光谱监测两种不同的方法评估每种化合物的亲电特性。在人结肠癌细胞中评估了类似物1a–q的潜在治疗效果以及在永生化肝细胞中的毒性。我们的结果表明，姜黄素类似物1e是一种有前景的抗结直肠癌药物，具有更高的稳定性和功效/安全性。
• Synthesis of novel curcumin analogues for inhibition of 11β-hydroxysteroid dehydrogenase type 1 with anti-diabetic properties
  作者：Xiaohuan Yuan、Hongzhi Li、He Bai、Zhijian Su、Qi Xiang、Chaonan Wang、Binghai Zhao、Yufei Zhang、Qihao Zhang、Yanhui Chu、Yadong Huang

  DOI：10.1016/j.ejmech.2014.03.012

  日期：2014.4

  In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which is responsible for the pharmacokinetic limitation of curcumin. We demonstrated that 4 of 9 curcumin analogues were selective inhibitors of human and rodent 11 beta-HSD1. The level of this inhibitor was 4-20 times more than that of curcumin. Curcumin analogues weakly inhibited 11 beta-HSD2, and further analyses revealed that these compounds were highly selective, favoring 11 beta-HSD1. These 4 curcumin analogues are potential therapeutic agents for type-2 diabetes by targeting 11 beta-HSD1. The compound 8 displays anti-diabetic properties in diabetic mice induced by streptozocin and high-fat-diet (STZHFD). (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin
  作者：Guang Liang、Xiaokun Li、Li Chen、Shulin Yang、Xudong Wu、Elaine Studer、Emily Gurley、Phillip B. Hylemon、Faqing Ye、Yueru Li、Huiping Zhou

  DOI：10.1016/j.bmcl.2007.12.068

  日期：2008.2

  Curcumin has been extensively studied for its anti-inflammatory activities. However, its potential beneficial effects on various disease preventions and treatments are limited by its unstable structure. The beta-diketone moiety renders curcumin to be rapidly metabolized by aldo -keto reductase in liver. In the present study, a series of curcumin analogues with more stable chemical structures were synthesized and several compounds showed an enhanced ability to inhibit lipopolysaccharide ( LPS)-induced TNF-alpha and IL-6 synthesis in macrophages. (C) 2007 Elsevier Ltd. All rights reserved.