di-O-benzoyl curcumin | 98886-39-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: di-O-benzoyl curcumin
• 英文别名: di-O-benzoylcurcumin；[4-[(1E,6E)-7-(4-benzoyloxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] benzoate
• CAS: 98886-39-6
• 化学式: C₃₅H₂₈O₈
• 分子量: 576.603
• InChiKey: TVDFVAPAHXSPDG-HBKJEHTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  di-O-benzoyl curcumin 、 2-氯乙醇 在 sodium ethanolate 、 吡啶 作用下， 以 乙醇 为溶剂， 反应 6.83h， 以183 mg的产率得到[4-[(1E,6E)-7-(4-benzoyloxy-3-methoxyphenyl)-4-(2-hydroxyethyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] benzoate
  参考文献：
  名称：

  Synthesis, antibacterial and antiviral properties of curcumin bioconjugates bearing dipeptide, fatty acids and folic acid

  摘要：

  Curcumin bioconjugates, viz. di-O-tryptophanylphenylalanine curcumin (2), di-O-decanoyl curcumin (3), di-O-pamitoyl curcumin (4), di-O-bis-(gamma,gamma)folyl curcumin (6), C-4-ethyl-O-gamma-folyl curcumin (8) and 4-O-ethyl-O-gamma-folyl curcumin (10) have been synthesized and tested for their antibacterial and antiviral activities. The conjugates 2, 3, 4, 6 and 8 have shown very promising antibacterial activity with MIC ranging between 0.09 and 0.67 mu M against Gram-positive cocci and Gram-negative bacilli. Further, the conjugates 2, 3, 6, 8 and 10 have been screened for their antiviral activities against HSV, VSV, FIPV, PIV-3, RSV and FHV and the molecules 2 and 3 have shown good results with EC50 0.011 mu M and 0.029 mu M against VSV and FIPV/FHV, respectively. However, the molecules did not show expected results against HIV-1 IIIB and ROD strains in MTT assay. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.002
• 作为产物：
  描述：

  curcumin 、 苯甲酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 以68%的产率得到di-O-benzoyl curcumin
  参考文献：
  名称：

  Pedersen, Uffe; Rasmussen, Preben B.; Lawesson, Sven-Olov, Liebigs Annalen der Chemie, 1985, # 8, p. 1557 - 1569

  摘要：

  DOI：

文献信息

• Three new coordination geometries of homoleptic Zn complexes of curcuminoids and their high antiproliferative potential
  作者：William Meza-Morales、Yair Alvarez-Ricardo、Marco A. Obregón-Mendoza、Antonino Arenaza-Corona、María Teresa Ramírez-Apan、Rubén A. Toscano、Juan Carlos Poveda-Jaramillo、Raúl G. Enríquez

  DOI：10.1039/d3ra00167a

  日期：——

  structure of a homoleptic zinc curcuminoid complex with square pyramidal geometry, we add herein three new geometries of homoleptic type complexes i.e. octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Octahedral geometry was observed in the new pseudo-polymorph of the DAC–Zn complex resulting from crystallization in DMF, while square-pyramidal geometry was obtained in DMSO. Improving crystallinity

  对于我们之前报道的具有方锥体几何形状的同配型姜黄素复合物的第一个晶体结构，我们在本文中添加了均配型复合物的三种新几何形状，即八面体、三方锥体和三方双锥体。在 DMF 中结晶产生的 DAC-Zn 复合物的新假多晶型物中观察到八面体几何形状，而在 DMSO 中获得四角锥体几何形状。提高结晶度涉及通过醚化和酯化抑制酚类相互作用。使用 SCXRD、IR、MS、EA、液体和固态 NMR 对这些配合物进行了完整表征。此外，还评估了所有复合物的细胞毒活性。在 U251 和 HCT-15 细胞系中，DiMeOC-Zn ( 7 ) 复合物的 IC 50值比顺铂高 8 或 22 倍，表明具有较高的抗增殖和治疗潜力。
• Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species
  作者：Chatchawan Changtam、Harry P. de Koning、Hasan Ibrahim、M. Sohail Sajid、Matthew K. Gould、Apichart Suksamrarn

  DOI：10.1016/j.ejmech.2009.11.035

  日期：2010.3

  The natural curcuminoids curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) have been chemically modified to give 46 analogs and 8 pairs of 1: 1 mixture of curcuminoid analogs and these parent curcuminoids and their analogs were assessed against protozoa of the Tryponosoma and Leishmania species. The parent curcuminoids exhibited low antitrypanosomal activity (EC50 for our drug-sensitive Trypanosoma brucei brucei line (WT) of compounds 1, 2 and 3 are 2.5, 4.6 and 7.7 mu M, respectively). Among 43 curcuminoid analogs and 8 pairs of 1: 1 mixture of curcuminoid analogs tested, 8 pure analogs and 5 isomeric mixtures of analogs exhibited high antitrypanosomal activity in sub-micromolar order of magnitude. Among these highly active analogs, 1,7-bis(4-hydroxy-3-methoxy-phenyl)hept-4-en-3-one (40) was the most active compound, with an EC50 value of 0.053 +/- 0.007 mu M; it was about 2-fold more active than the standard veterinary drug diminazene aceturate (EC50 0.12 +/- 0.01 mu M). Using a previously characterized diminazene-resistant T. b, brucei (TbAT1-KO) and a derived multi-drug resistant line (B48), no cross-resistance of curcuminoids was observed to the diamidine and melaminophenyl arsenical drugs that are the current treatments. Indeed, curcuminoids carrying a conjugated keto (enone) motif, including 40, were significantly more active against 7: b. brucei B48. This enone motif was found to contribute to particularly high trypanocidal activity against all Trypanosoma species and strains tested. The parent curcuminoids showed low antileishmanial activity (EC50 values of compounds 1 and 2 for Leishmania mexicana amastigotes are 16 +/- 3 and 37 +/- 6 mu M. respectively) while the control drug, pentamidine, displayed an EC50 of 16 +/- 2 mu M. Among the active curcuminoid analogs, four Compounds exhibited EC50 values of less than 5 mu M against Leishmania major promastigotes and four against L mexicana amastigotes. No significant difference in sensitivity to curcuminoids between L. major promastigotes and L. mexicana amastigotes was observed. The parent curcuminoids and most of their analogs were also tested for their toxicity against human embryonic kidney (HEK) cells. All the curcuminoids exhibited lower toxicity to HEK cells than to T b. brucei bloodstream forms and only one of the tested compounds showed significantly higher activity against HEK cells than curcumin (1). The selectivity index for T b. brucei ranged from 3-fold to 1500-fold. The selectivity index for the most active analog, the enone 40, was 453-fold. (C) 2009 Elsevier Masson SAS. All rights reserved.