(1E,4E)-1,5-bis(3,4-dihydroxyphenyl)penta-1,4-diene-3-one

• 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(3,4-dihydroxyphenyl)penta-1,4-diene-3-one
• 英文别名: (1E,4E)-1,5-bis(3,4-dihydroxyphenyl)-1,4-pentadien-3-one；(1E,4E)-1,5-bis(3,4-dihydroxyphenyl)pent-1,4-diene-3-one；(1E,4E)-1,5-bis(3,4-dihydroxyphenyl)penta-1,4-dien-3-one；1,5-bis(3,4-dihydroxyphenyl)-1,4-pentadiene-3-one；1,5-bis(3,4-dihydroxyphenyl)-1,4-pentadien-3-one；(1E,4E)-1,5-bis(3,4-dihydroxyphenyl)-1,4-pentadiene-3-one
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: MOPYIPOZUDHBJM-IJIVKGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 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：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二(四氢吡喃-2-氧基)苯甲醛 在 barium hydroxide octahydrate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 (1E,4E)-1,5-bis(3,4-dihydroxyphenyl)penta-1,4-diene-3-one
  参考文献：
  名称：

  Geometrically and Conformationally Restrained Cinnamoyl Compounds as Inhibitors of HIV-1 Integrase:  Synthesis, Biological Evaluation, and Molecular Modeling

  摘要：

  Various cinnammoyl-based structures were synthesized and tested in enzyme assays as inhibitors of the HIV-1 integrase (IN). The majority of compounds were designed as geometrically or conformationally constrained analogues of caffeic acid phenethyl ester (CAPE) and were characterized by a syn disposition of the carbonyl group with respect to the vinylic double bond. Since the cinnamoyl moiety present in flavones such as quercetin (inactive on HIV-1-infected cells) is frozen in an anti arrangement, it was hoped that fixing our compounds in a syn disposition could favor anti-HIV-1 activity in cell-based assays. Geometrical and conformational properties of the designed compounds were taken into account through analysis of X-ray structures available from the Cambridge Structural Database. The polyhydroxylated analogues were prepared by reacting 3,4-bis(tetrahydropyran-2-yloxy)benzaldehyde with various compounds having active methylene groups such as 2-propanone, cyclopentanone, cyclohexanone, 1,3-diacetylbenzene, 2,4-dihydroxyacetophenone, 2,3-dihydro-1-indanone, 2,3-dihydro-1,3-indandione, and others. While active against both 3'-processing and strand-transfer reactions, the new compounds, curcumin included, failed to inhibit the HIV-1 multiplication in acutely infected MT-4 cells. Nevertheless, they specifically inhibited the enzymatic reactions associated with IN, being totally inactive against other viral (HIV-1 reverse transcriptase) and cellular (RNA polymerase II) nucleic acid-processing enzymes. On the other hand, title compounds were endowed with remarkable antiproliferative activity, whose potency correlated neither with the presence of catechols (possible source of reactive quinones) nor with inhibition of topoisomerases. The SARs developed for our compounds led to novel findings concerning the molecular determinants of IN inhibitory activity within the class of cinnamoyl-based structures. We hypothesize that these compounds bind to IN featuring the cinnamoyl residue C=C-C=O in a syn disposition, differently from flavone derivatives characterized by an anti arrangement about the same fragment. Certain inhibitors, lacking one of the two pharmacophoric catechol hydroxyls, retain moderate potency thanks to nonpharmacophoric fragments (i.e., a m-methoxy group in curcumin) which favorably interact with an "accessory" region of IN. This region is supposed to be located adjacent to the binding site accommodating the pharmacophoric dihydroxycinnamoyl moiety. Disruption of coplanarity in the inhibitor structure abolishes activity owing to poor shape complementarity with the target or an exceedingly high strain energy of the coplanar conformation.

  DOI：

  10.1021/jm9707232

文献信息

• Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
  作者：Shoaib Muhammad、Muhammad Naveed Javed、Firdous Imran Ali、Ahmed Bari、Imran Ali Hashmi

  DOI：10.1016/j.molliq.2019.112372

  日期：2020.2

  (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs

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  DOI：10.1016/j.bmc.2005.11.035

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  申请人：中国人民解放军第二军医大学

  公开号：CN106800547B

  公开（公告）日：2019-07-23

  本发明涉及一种双取代芳基类化合物及其应用，所述的双取代芳基类化合物结构如式I、II或III所示，通过实验验证发现该类双取代芳基类化合物可以与唑类抗真菌药物共同使用，可提高耐药菌对唑类药物的敏感性，实现逆转耐药，因此本发明为临床耐药真菌的治疗提供了一种新途径。
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  日期：——

  monoketone derivatives of curcumin were synthesized to investigate the synergy with fluconazole against fluconazole-resistant Candida spp. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant C. albicans, C. tropicalis and C. krusei in vitro. Most of these compounds showed

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• Curcumin Analogs as Potent Aldose Reductase Inhibitors
  作者：Zhi-Yun Du、Ya-Dan Bao、Zhong Liu、Wei Qiao、Lin Ma、Zhi-Shu Huang、Lian-Quan Gu、Albert S. C. Chan

  DOI：10.1002/ardp.200500205

  日期：2006.3

  study, curcuminoids isolated from curcuma longa were demonstrated to possess inhibitory activities on bovine lens aldose reductase. In order to find more potent aldose reductase inhibitor, curcumin analogs were synthesized and evaluated for their ability to inhibit bovine lens aldose reductase enzyme. The results indicated that the compounds with tetrahydroxyl groups, 2,6‐bis(3,4‐dihydroxybenzylidene)cyclohexanone

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