(3Z,5E)-6-(3,4-dimethoxyphenyl)-4-hydroxyhexa-3,5-dien-2-one | 443308-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3Z,5E)-6-(3,4-dimethoxyphenyl)-4-hydroxyhexa-3,5-dien-2-one
• 英文别名: 4-hydroxy-6-(3,4-dimethoxyphenyl)hexa-3,5-dien-2-one
• CAS: 443308-31-4
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: MGZOSXSTGQXJPL-HOGPSILUSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  437.1±45.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3Z,5E)-6-(3,4-dimethoxyphenyl)-4-hydroxyhexa-3,5-dien-2-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以60%的产率得到(3Z,5E)-6-(3,4-dihydroxyphenyl)-4-hydroxyhexa-3,5-dien-2-one
  参考文献：
  名称：

  Venkateswarlu; Ramachandra; Sethuramu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 4, p. 875 - 877

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酰氯 在 水 、 sodium hydride 、 sodium chloride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 8.5h， 生成 (3Z,5E)-6-(3,4-dimethoxyphenyl)-4-hydroxyhexa-3,5-dien-2-one
  参考文献：
  名称：

  Venkateswarlu; Ramachandra; Sethuramu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 4, p. 875 - 877

  摘要：

  DOI：

文献信息

• Synthesis, characterization, DNA/BSA interactions and in vitro cytotoxicity study of palladium(II) complexes of hispolon derivatives
  作者：Xiaonan Wei、Yaxing Yang、Jiangfeng Ge、Xue Lin、Dandan Liu、Shuxiang Wang、Jinchao Zhang、Guoqiang Zhou、Shenghui Li

  DOI：10.1016/j.jinorgbio.2019.110857

  日期：2020.1

  Thirteen novel palladium(II) complexes of the general formula [Pd(bipy)(O,O′-dkt)](PF6), (where bipy is 2,2′-bipyridine and O,O′-dkt is β-diketonate ligand hispolon or its derivative) have been prepared through a metal-ligand coordination method that involves spontaneous formation of the corresponding diketonate scaffold. The obtained palladium(II) complexes have been characterized by NMR spectroscopy

  十三新颖钯（II）通式的配合物[钯（联吡啶）（ø，ö '-dkt）]（PF 6），（其中，联吡啶是2,2'-联吡啶和ø，ö '-dkt就是β-已经通过涉及自发形成相应的二酮酸酯支架的金属-配体配位方法制备了二酮酸酯配体组胺或其衍生物）。所获得的钯（II）配合物已经通过NMR光谱，ESI-质谱和元素分析进行​​了表征。细胞毒性分析表明，大多数获得的钯（II）配合物在三种人类癌细胞系中均显示出有希望的生长抑制作用。流式细胞仪分析显示复杂的3e可能会促进细胞内活性氧（ROS）积累并导致癌细胞死亡。N-乙酰基-L-半胱氨酸（NAC）抑制HeLa细胞中ROS积累和挽救细胞活力，表明ROS产生的增加与复合物3e的细胞毒性之间可能存在联系。流式细胞仪分析还显示复合物3e导致细胞周期停滞在G2 / M期并破坏了线粒体膜电位，促进了ROS的生成并导致肿瘤细胞凋亡。复杂3e的相互作用牛胸腺DNA（CT-DNA
• Antitumor Agents. 250. Design and Synthesis of New Curcumin Analogues as Potential Anti-Prostate Cancer Agents
  作者：Li Lin、Qian Shi、Alexander K. Nyarko、Kenneth F. Bastow、Chin-Chung Wu、Ching-Yuan Su、Charles C.-Y Shih、Kuo-Hsiung Lee

  DOI：10.1021/jm051043z

  日期：2006.6.1

  In a continuing study of curcumin analogues as potential drug candidates to treat prostate cancer at both androgen-dependent and androgen-refractory stages, we designed and synthesized over 40 new analogues classified into four series: monophenyl analogues ( series A), heterocycle-containing analogues ( series B), analogues bearing various substituents on the phenyl rings ( series C), and analogues with various linkers ( series D). These new compounds were tested for cytotoxicity against two human prostate cancer cell lines, androgen-dependent LNCaP and androgen-independent PC-3. Antiandrogenic activity was also evaluated in LNCaP cells and PC-3 cells transfected with wild-type androgen receptor. Ten compounds possessed potent cytotoxicity against both LNCaP and PC-3 cells, seven only against LNCaP, and one solely against PC-3. This study established an advanced structure-activity relationship ( SAR), and these correlations will guide the further design of new curcumin analogues with better anti-prostate cancer activity.
• Synthesis of the First Ferrocenyl Derivatives of Curcuminoids
  作者：Anusch Arezki、Emilie Brulé、Gérard Jaouen

  DOI：10.1021/om900003g

  日期：2009.3.23

  The synthesis of curcuminoids covalently bound to a ferrocenyl moiety was investigated using two strategies: a ferrocenyl unit was incorporated during the synthesis of 3,4-dimethylcurcumin using a Knoevenagel condensation, and the enolates of 3,5-dimethylcurcumin and curcumin, previously protected, underwent a 1,4-addition on ferrocenyl propynone.
• US9562025B2
  申请人：——

  公开号：US9562025B2

  公开（公告）日：2017-02-07
• Venkateswarlu; Ramachandra; Sethuramu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 4, p. 875 - 877
  作者：Venkateswarlu、Ramachandra、Sethuramu、Subbaraju, Gottumukkala V.

  DOI：——

  日期：——