acetic acid 4-[3-oxo-3-(2,4,6-triacetoxy-phenyl)propyl]phenyl ester | 42385-89-7

• 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: acetic acid 4-[3-oxo-3-(2,4,6-triacetoxy-phenyl)propyl]phenyl ester
• 英文别名: phloretin triacetate；3-(4-acetoxy-phenyl)-1-(2,4,6-triacetoxy-phenyl)-propan-1-one；3-(4-Acetoxy-phenyl)-1-(2,4,6-triacetoxy-phenyl)-propan-1-on；3,5-Bis(acetyloxy)-2-{3-[4-(acetyloxy)phenyl]propanoyl}phenyl acetate；[4-[3-oxo-3-(2,4,6-triacetyloxyphenyl)propyl]phenyl] acetate
• CAS: 42385-89-7
• 化学式: C₂₃H₂₂O₉
• 分子量: 442.422
• InChiKey: OUTPMVGHRKAIEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  acetic acid 4-[3-oxo-3-(2,4,6-triacetoxy-phenyl)propyl]phenyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以7.5%的产率得到间苯三酚
  参考文献：
  名称：

  Funatsu, Takakazu; Iriye, Ryozo; Takai, Hideyuki, Agricultural and Biological Chemistry, 1989, vol. 53, # 11, p. 3087 - 3090

  摘要：

  DOI：
• 作为产物：
  描述：

  根皮素 、 乙酸酐 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以85%的产率得到acetic acid 4-[3-oxo-3-(2,4,6-triacetoxy-phenyl)propyl]phenyl ester
  参考文献：
  名称：

  一系列根皮素衍生物的合成、晶体结构和生物学评价

  摘要：

  报道了从根皮素一步合成根皮素衍生物 2-11 的方法，收率很好。它们的结构通过1H-NMR、13C-NMR和MS表征，8和11的结构通过X射线衍射分析确定。提出了形成 9-11 的机制。与抗癌药物多西紫杉醇相比，根皮素、根皮素衍生物和根皮苷对 MDA-MB-231、SPC-A1、A549、MCF-7 和 EC109 细胞系表现出中等的细胞毒性。在所有测试的化合物中，7 种对五种细胞系表现出最强的细胞毒性，并且在 MDA-MB-231 细胞中比多西他赛更有活性。我们的研究结果表明，这些衍生物作为抗癌剂的进一步开发具有广阔的前景。

  DOI：

  10.3390/molecules191016447

文献信息

• Ciamician; Silber, Chemische Berichte, 1895, vol. 28, p. 1393
  作者：Ciamician、Silber

  DOI：——

  日期：——
• Michael, Chemische Berichte, 1894, vol. 27, p. 2686
  作者：Michael

  DOI：——

  日期：——
• Antileishmanial activities of dihydrochalcones from piper elongatum and synthetic related compounds. Structural requirements for activity
  作者：Alicia Hermoso、Ignacio A Jiménez、Zulma A Mamani、Isabel L Bazzocchi、José E Piñero、Angel G Ravelo、Basilio Valladares

  DOI：10.1016/s0968-0896(03)00406-1

  日期：2003.9

  Two dihydrochalcones (1 and 2) were isolated from Piper elongatum Vahl by activity-guided fractionation against extracellular promastigotes of Leishmania braziliensis in vitro. Their structures were elucidated by spectral analysis, including homonuclear and heteronuclear correlation NMR experiments. Derivatives 3-7 and 20 synthetic related compounds (8-27) were also assayed to establish the structural requirements for antileishmanial activity. Compounds 1-11 that proved to be more active that ketoconazol, used as positive control, were further assayed against promastigotes of Leishmania tropica and Leishmania infantum. Compounds 7 and 11, with a C-6-C-3-C-6 System, proved to be the most promising compounds, with IC50 values of 2.98 and 3.65 mug/mL, respectively, and exhibited no toxic effect on macrophages (around 90% viability). Correlation between the molecular structures and antileishmanial activity is discussed in detail. (C) 2003 Elsevier Ltd. All rights reserved.
• FUNATSU, TAKAKAZU;IRIYE, RYOZO;TAKAI, HIDEYUKI;HIROTA, MITSURU, AGR. AND BIOL. CHEM., 53,(1989) N1, C. 3087-3089
  作者：FUNATSU, TAKAKAZU、IRIYE, RYOZO、TAKAI, HIDEYUKI、HIROTA, MITSURU

  DOI：——

  日期：——
• Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives
  作者：Li Wang、Zheng-Wei Li、Wei Zhang、Rui Xu、Fei Gao、Yang-Feng Liu、Ya-Jun Li

  DOI：10.3390/molecules191016447

  日期：——

  A one-step synthesis of phloretin derivatives 2–11 from phloretin in good to excellent yields is reported. Their structures were characterized by 1H-NMR, 13C-NMR and MS, and the structures of 8 and 11 were determined by X-ray diffraction analysis. A mechanism for the formation of 9–11 is proposed. Compared with the anticancer drug docetaxel, phloretin, phloretin derivatives and phlorizin exhibited

  报道了从根皮素一步合成根皮素衍生物 2-11 的方法，收率很好。它们的结构通过1H-NMR、13C-NMR和MS表征，8和11的结构通过X射线衍射分析确定。提出了形成 9-11 的机制。与抗癌药物多西紫杉醇相比，根皮素、根皮素衍生物和根皮苷对 MDA-MB-231、SPC-A1、A549、MCF-7 和 EC109 细胞系表现出中等的细胞毒性。在所有测试的化合物中，7 种对五种细胞系表现出最强的细胞毒性，并且在 MDA-MB-231 细胞中比多西他赛更有活性。我们的研究结果表明，这些衍生物作为抗癌剂的进一步开发具有广阔的前景。