mono-O-(2-hydroxyethyl)curcumin | 1220971-44-7

• 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: mono-O-(2-hydroxyethyl)curcumin
• 英文别名: (1E,6E)-1-[4-(2-hydroxyethoxy)-3-methoxy-phenyl]-7-(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione；(1E,6E)-1-[4-(2-hydroxyethoxy)-3-methoxyphenyl]-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• CAS: 1220971-44-7
• 化学式: C₂₃H₂₄O₇
• 分子量: 412.439
• InChiKey: XXYYXNNYUJKCQX-FCXRPNKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  mono-O-(2-hydroxyethyl)curcumin 、 (2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]-5-(4-nitrophenoxy)-5-oxopentanoic acid 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 反应 5.0h， 生成 4-O-ethyl-O-γ-folyl curcumin
  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：

  姜黄素 、 2-氯乙醇 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 7.0h， 以48%的产率得到mono-O-(2-hydroxyethyl)curcumin
  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

文献信息

• Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity
  作者：Chatchawan Changtam、Poonpilas Hongmanee、Apichart Suksamrarn

  DOI：10.1016/j.ejmech.2010.07.003

  日期：2010.10

  bisdemethoxycurcumin (3), the curcuminoid constituents of the medicinal plant Curcuma longa L., have been structurally modified to 55 analogs and antimycobacterial activity against Mycobacterium tuberculosis has been evaluated. Among the highly active curcuminoids, the isoxazole analogs are the most active group, with mono-O-methylcurcumin isoxazole (53) being the most active compound (MIC 0.09 μg/mL). It was

  姜黄素（1），去甲氧基姜黄素（2）和双去甲氧基姜黄素（3）（药用植物姜黄的姜黄素成分）已在结构上修饰为55个类似物，并已评估了其对结核分枝杆菌的抗分枝杆菌活性。在高活性姜黄素类化合物中，异恶唑类似物是活性最高的基团，单-O-甲基姜黄素异恶唑（53）是活性最高的化合物（MIC 0.09μg/ mL）。它的活性比母体化合物姜黄素（1）高1131倍，分别比标准药物卡那霉素和异烟肼高18倍和2倍。化合物53还显示出对耐多药结核分枝杆菌临床分离株的高活性，MIC值为0.195–3.125μg/ mL。姜黄素类似物表现出抗分枝杆菌活性的结构要求是在异戊基环上存在一个异恶唑环和两个不饱和键。紧密连接于异恶唑环的氮官能团的芳环上合适的对烷氧基的存在和另一个芳环上的游离对羟基的存在增强了生物活性。
• 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.
• ORGANIC-INORGANIC COMPOSITE, COMPOSITION FOR FORMATION OF ORGANIC-INORGANIC COMPOSITE, AND INK
  申请人：Sumitomo Osaka Cement Co., Ltd.

  公开号：EP2532714B1

  公开（公告）日：2017-03-08
• US9540491B2
  申请人：——

  公开号：US9540491B2

  公开（公告）日：2017-01-10
• Synthesis, antibacterial and antiviral properties of curcumin bioconjugates bearing dipeptide, fatty acids and folic acid
  作者：Ramendra K. Singh、Diwakar Rai、Dipti Yadav、A. Bhargava、J. Balzarini、E. De Clercq

  DOI：10.1016/j.ejmech.2009.12.002

  日期：2010.3

  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.