(E)-3-(trioxsalen-4'-yl)propenoic acid | 1114540-07-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (E)-3-(trioxsalen-4'-yl)propenoic acid
• 英文别名: (E)-3-(trioxsalen-4'-yl)acrylic acid；TRAA；(E)-3-(2,5,9-trimethyl-7-oxofuro[3,2-g]chromen-3-yl)prop-2-enoic acid
• CAS: 1114540-07-6
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: GVMQZETUHCETLL-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 (E)-3-(trioxsalen-4'-yl)propenoic acid 在 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以71%的产率得到succinimidyl (E)-3-(trioxsalen-4'-yl)propenoate
  参考文献：
  名称：

  Synthetic Studies towards the Development of Psoralen-Acidic Retinoid Conjugates and Hybrids

  摘要：

  利用亲电芳香取代反应对三氧沙林进行化学修饰，然后进行维蒂希反应、赫克反应或铃木偶联反应，就可以得到 C4′修饰的三氧沙林衍生物，这些衍生物被成功地用于制备多种三氧沙林与多胺型或酯型阿曲汀的共轭物以及三氧沙林-阿曲汀混合物。

  DOI：

  10.1055/s-0028-1083189
• 作为产物：
  描述：

  tert-butyl (E)-3-(trioxsalen-4'-yl)propenoate 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以95%的产率得到(E)-3-(trioxsalen-4'-yl)propenoic acid
  参考文献：
  名称：

  Synthetic Studies towards the Development of Psoralen-Acidic Retinoid Conjugates and Hybrids

  摘要：

  利用亲电芳香取代反应对三氧沙林进行化学修饰，然后进行维蒂希反应、赫克反应或铃木偶联反应，就可以得到 C4′修饰的三氧沙林衍生物，这些衍生物被成功地用于制备多种三氧沙林与多胺型或酯型阿曲汀的共轭物以及三氧沙林-阿曲汀混合物。

  DOI：

  10.1055/s-0028-1083189

文献信息

• Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives
  作者：Stavros E. Bariamis、Marilena Marin、Constantinos M. Athanassopoulos、Christos Kontogiorgis、Zinovia Tsimali、Dionissios Papaioannou、Giovanni Sindona、Giovanni Romeo、Konstantinos Avgoustakis、Dimitra Hadjipavlou-Litina

  DOI：10.1016/j.ejmech.2012.11.043

  日期：2013.2

  respectively. The 8-MOP analogs 19 and 24, incorporating at position 5 of the psoralen nucleus a butyl acrylate or a tert-butyl cinnamate moiety, were the most powerful inhibitors of soybean LOX and inhibited effectively lipid peroxidation. Analog 19 was a more potent anti-inflammatory agent than the reference compound indomethacin and of comparable cytocompatibility to 8-MOP whereas analog 24 was a weaker

  合成了一系列适合于结构抗氧化/抗炎活性关系研究的5-和8-甲氧基补骨脂素（MOP）类似物，使用N-溴糖精对MOP进行选择性单溴化，并利用Heck反应或Suzuki偶联或Suzuki偶联，然后进行Wittig反应以分别安装丙烯酸酯或苯甲酸酯或肉桂酸酯类型的侧链。在补骨脂素核的5位掺入丙烯酸丁酯或肉桂酸叔丁酯部分的8-MOP类似物19和24是大豆LOX的最有效抑制剂，可有效抑制脂质过氧化。模拟19与消炎痛相比，消炎痛是一种比参考化合物消炎痛更有效的抗炎药，并且与8-MOP具有相当的细胞相容性，而与消炎痛相比，类似物24的消炎抑制剂弱，并且与8-MOP相比，其细胞毒性明显更高。根据结构特征讨论了生物学测试的结果。
• Does conjugation of antioxidants improve their antioxidative/anti-inflammatory potential?
  作者：Dimitra Hadjipavlou-Litina、George E. Magoulas、Stavros E. Bariamis、Denis Drainas、Konstantinos Avgoustakis、Dionissios Papaioannou

  DOI：10.1016/j.bmc.2010.10.012

  日期：2010.12

  A series of symmetric and asymmetric spermine (SPM) conjugates with all-trans-retinoic acid (ATRA), acitretin (ACI), (E)-3-(trioxsalen-4'-yl)acrylic acid (TRAA) and L-DOPA, amides of ACI, L-DOPA and TRAA with 1-aminobutane, benzylamine, dopamine and 1,12-diaminobutane as well as hybrid conjugates of O,O'-dimethylcaffeic acid (DMCA) with TRAA or N-fumaroyl-indole-3-carboxanilide (FICA) and 2-(2-aminoethoxy) ethanol were synthesized and their antioxidant properties were studied. The reducing activity (RA)% of the compounds were evaluated using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical-scavenging assay and found to be in the range 0-92(20 min)%/96(60 min)% at 100 mu M, the most powerful being the conjugates L-DOPA-SPM-L-DOPA (8, RA = 89%/96%) and L-DOPA-dopamine (13, RA = 92%/92%). Conjugate DMCA-NH(CH2CH2O)(2)-FICA (14) was the most powerful LOX inhibitor with IC50 33.5 mu M, followed by the conjugates ACI-NHCH2Ph (10, IC50 40.5 mu M), ACI-SPM-TRAA (7, IC50 41.5 mu M), DMCA-NH(CH2CH2O)(2)-TRAA (15, IC50 65 mu M), 13 (IC50 81.5 mu M) and ACI-dopamine (11, IC50 87 mu M). The most potent inhibitors of lipid peroxidation at 100 mu M were the conjugates 15 (98%) and ACI-SPM-ACI (4, 97%) whereas all other compounds showed activities comparable or lower than trolox. The most interesting compounds, namely ATRA-SPM-ATRA (3), 4, 10, 11 and 15, as well as unconjugated compounds such as ATRA and dopamine, were studied for their anti-inflammatory activity in vivo on rat paw oedema induced by Carrageenan and found to exhibit, for doses of 0.01 mmol/mL of conjugates per Kg of rat body weight, weaker anti-inflammatory activities (3.6-40%) than indomethacin (47%) with conjugate 3 being the most potent (40%) in this series of compounds. The cytocompatibility of selected compounds was evaluated by the viability of RAMEC cells in the presence of different concentrations (0.5-50 mu M) of the compounds. Conjugates 3 (IC50 2.6 mu M) and 4 (IC50 4.7 mu M) were more cytotoxic than the corresponding unconjugated retinoids ATRA (IC50 18.3 mu M) and ACI (IC50 14.6 mu M), whereas conjugate 15 (IC50 12.9 mu M) was less cytotoxic than either DCSP (IC50 11.3 mu M) or the tert-butyl ester of TRAA (IC50 2.9 mu M). (C) 2010 Elsevier Ltd. All rights reserved.
• Synthetic Studies towards the Development of Psoralen-Acidic Retinoid Conjugates and Hybrids
  作者：Dionissios Papaioannou、Maria Militsopoulou、Stavros Bariamis、Constantinos Athanassopoulos

  DOI：10.1055/s-0028-1083189

  日期：——

  The chemical modification of trioxsalen using electrophilic aromatic substitution reactions, followed by either Wittig or Heck reactions or Suzuki coupling, allowed for ready access to C4′ modified trioxsalen derivatives that were successfully used for the preparation of a variety of trioxsalen conjugates with acitretin of either the polyamine or the ester type and trioxsalen-acitretin hybrids.

  利用亲电芳香取代反应对三氧沙林进行化学修饰，然后进行维蒂希反应、赫克反应或铃木偶联反应，就可以得到 C4′修饰的三氧沙林衍生物，这些衍生物被成功地用于制备多种三氧沙林与多胺型或酯型阿曲汀的共轭物以及三氧沙林-阿曲汀混合物。