4',3,4-tris(tetrahydropyran-2-yloxy)chalcone | 130600-77-0

• 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: 4',3,4-tris(tetrahydropyran-2-yloxy)chalcone
• 英文别名: (E)-3-[3,4-bis(oxan-2-yloxy)phenyl]-1-[4-(oxan-2-yloxy)phenyl]prop-2-en-1-one
• CAS: 130600-77-0
• 化学式: C₃₀H₃₆O₇
• 分子量: 508.612
• InChiKey: KKNWMCQDHGWAFL-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4',3,4-tris(tetrahydropyran-2-yloxy)chalcone 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-prop-2-en-1-one
  参考文献：
  名称：

  3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4-dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 6-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5-lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.

  DOI：

  10.1021/jm00076a019
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 barium dihydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 4',3,4-tris(tetrahydropyran-2-yloxy)chalcone
  参考文献：
  名称：

  3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4-dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 6-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5-lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.

  DOI：

  10.1021/jm00076a019

文献信息

• Geometrically and Conformationally Restrained Cinnamoyl Compounds as Inhibitors of HIV-1 Integrase:  Synthesis, Biological Evaluation, and Molecular Modeling
  作者：Marino Artico、Roberto Di Santo、Roberta Costi、Ettore Novellino、Giovanni Greco、Silvio Massa、Enzo Tramontano、Maria E. Marongiu、Antonella De Montis、Paolo La Colla

  DOI：10.1021/jm9707232

  日期：1998.10.1

  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.
• Chalcone derivatives and process for producing the same
  申请人：DAINIPPON INK AND CHEMICALS, INC.

  公开号：EP0370461B1

  公开（公告）日：1995-06-28
• POLYMERIZABLE COMPOUND, LIQUID CRYSTAL COMPOSITION, AND LIQUID CRYSTAL DISPLAY DEVICE
  申请人：JNC CORPORATION

  公开号：US20140346399A1

  公开（公告）日：2014-11-27

  A liquid crystal composition and a liquid crystal display device which includes the composition are provided. The liquid crystal composition contains a specific compound having a polymerizable group as a first component, and may contain a specific compound having a large negative dielectric anisotropy and a low minimum temperature as a second component, or a specific compound having a small viscosity or a large maximum temperature as a third component. The liquid crystal composition satisfies at least one of the following characteristics: a high maximum temperature of a nematic phase, a low minimum temperature of the nematic phase, a small viscosity, a suitable optical anisotropy, a large negative dielectric anisotropy, a large specific resistance, a high stability to ultraviolet light and a high stability to heat. Alternatively, a liquid crystal composition having a suitable balance regarding at least two of the aforementioned characteristics is also provided.
• US9139672B2
  申请人：——

  公开号：US9139672B2

  公开（公告）日：2015-09-22