(E)-2-(4-methoxystyryl)-6-bromo-4H-chromen-4-one | 1375152-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-2-(4-methoxystyryl)-6-bromo-4H-chromen-4-one
• 英文别名: (E)-6-bromo-2-(4-methoxystyryl)-chromone；6-bromo-2-[(E)-2-(4-methoxyphenyl)ethenyl]chromen-4-one
• CAS: 1375152-68-3
• 化学式: C₁₈H₁₃BrO₃
• 分子量: 357.203
• InChiKey: ZGCYJSHVTUTINU-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-methoxystyryl)-6-bromo-4H-chromen-4-one 在 盐酸 、 四(三苯基膦)钯 、 sodium ¹²⁴iodide 、 双氧水 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 7.05h， 生成 (E)-6-iodo-2-(4-methoxystyryl)chromone
  参考文献：
  名称：

  Development of alkoxy styrylchromone derivatives for imaging of cerebral amyloid-β plaques with SPECT

  摘要：

  We report here the development of radioiodinated styrylchromone derivatives with alkoxy groups as single photon emission computed tomography (SPECT) imaging probes for cerebral amyloid-beta (A beta) plaques. Among the derivatives, the methoxy derivative 14 and the dimethoxy derivative 15 displayed relatively high affinity for the A beta(1-42) aggregates with K-i values of 22 and 46 nM, respectively. Fluorescent imaging demonstrated that 14 and 15 clearly labeled thioflavin-S positive A beta plaques in the brain sections of Tg2576 transgenic mice. In the in vivo studies, [I-125]14 and [I-125]15 showed high initial brain uptake expressed as the percentage of the injected dose per gram (2.25% and 2.49% ID/g at 2 min, respectively) with favorable clearance (0.12% and 0.20% ID/g at 180 min, respectively) from the brain tissue of normal mice. Furthermore, in vitro autoradiography confirmed that [I-125]15 binds thioflavin-S positive regions in Tg2576 mouse brain sections. The derivative 15 may be a potential scaffold for the development of in vivo imaging probes targeting A beta plaques in the brain. In particular, further structural modifications are required to improve the compounds binding affinity for A beta. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.048
• 作为产物：
  描述：

  2-羟基-5-溴苯乙酮 在 氯化亚砜 、 硫酸 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 5.5h， 生成 (E)-2-(4-methoxystyryl)-6-bromo-4H-chromen-4-one
  参考文献：
  名称：

  Development of alkoxy styrylchromone derivatives for imaging of cerebral amyloid-β plaques with SPECT

  摘要：

  We report here the development of radioiodinated styrylchromone derivatives with alkoxy groups as single photon emission computed tomography (SPECT) imaging probes for cerebral amyloid-beta (A beta) plaques. Among the derivatives, the methoxy derivative 14 and the dimethoxy derivative 15 displayed relatively high affinity for the A beta(1-42) aggregates with K-i values of 22 and 46 nM, respectively. Fluorescent imaging demonstrated that 14 and 15 clearly labeled thioflavin-S positive A beta plaques in the brain sections of Tg2576 transgenic mice. In the in vivo studies, [I-125]14 and [I-125]15 showed high initial brain uptake expressed as the percentage of the injected dose per gram (2.25% and 2.49% ID/g at 2 min, respectively) with favorable clearance (0.12% and 0.20% ID/g at 180 min, respectively) from the brain tissue of normal mice. Furthermore, in vitro autoradiography confirmed that [I-125]15 binds thioflavin-S positive regions in Tg2576 mouse brain sections. The derivative 15 may be a potential scaffold for the development of in vivo imaging probes targeting A beta plaques in the brain. In particular, further structural modifications are required to improve the compounds binding affinity for A beta. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.048

文献信息

• Synthesis and evaluation of antioxidant activity of 2-styrylchromones
  作者：Shrinivas P. Pawar、Dasharath D. Kondhare、P. K. Zubaidha

  DOI：10.1007/s00044-012-0069-z

  日期：2013.2

  oestrogenic and antibacterial activities, in particular the antioxidant behavior of these compounds continue to draw attention of researchers. In the present communication a series of halo substituted 2-styrylchromones 4a–4k were prepared and tested for the antioxidant activity by using DPPH (1, 1 diphenyl 2, picryl hydrazyl) method, and among the synthesized compounds 4e and 4h shows strong antioxidant activity

  抗氧化剂正在作为潜在的预防和治疗剂出现，它们可以清除自由基，否则会破坏活性氧并防止其引起的损害。自由基与多种疾病的发病机理有关，如癌症，糖尿病，心血管疾病，自身免疫疾病，神经退行性疾病，并与衰老有关。色酮及其衍生物具有重要的生物学活性，例如抗肿瘤，抗肝毒，抗炎，抗痉挛，雌激素和抗菌活性，特别是这些化合物的抗氧化性能继续引起研究人员的注意。在本来文中，一系列卤素取代的2-苯乙烯基色酮4a – 4k制备并通过DPPH（1，1，二苯基2，吡啶基肼基）方法测试抗氧化剂的活性，在合成的化合物4e和4h中显示出强的抗氧化剂活性，而其余化合物在正常范围内显示出抗氧化剂活性。