1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-thienyl)-prop-2-en-1-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-thienyl)-prop-2-en-1-one
• 英文别名: (E)-1-(5-bromofuran-2-yl)-3-[5-(dimethylamino)thiophen-2-yl]prop-2-en-1-one
• 化学式: C₁₃H₁₂BrNO₂S
• 分子量: 326.214
• InChiKey: ATMABEAVMGJRTM-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  61.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(5-溴-2-呋喃基)乙酮 、 5-(二甲氨基)-2-噻吩甲醛 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以11.4%的产率得到1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-thienyl)-prop-2-en-1-one
  参考文献：
  名称：

  Structure–activity relationship of chalcones and related derivatives as ligands for detecting of β-amyloid plaques in the brain

  摘要：

  A series of novel chalcones and their related derivatives were synthesized and evaluated as beta-amyloid imaging probes. In the structure-activity relationship of binding affinities to synthetic A beta(1-42) aggregates, compound 14 displayed the highest binding affinity in vitro. Amyloid plaques in the Alzheimer's model mouse brain were visualized with 14. In biodistribution studies using normal mice, [I-125]14 showed good brain uptake (2.56% ID/g, 2 min postinjection) and rapid washout from the brain (0.21% ID/g, 60 min postinjection). These results suggest that [I-125]14 should be further investigated as a potentially useful P-amyloid imaging probe.

  DOI：

  10.1016/j.bmc.2007.06.055

文献信息

• COMPOSITION FOR DIAGNOSIS OF AMYLOID-RELATED DISEASE
  申请人：Nakayama Morio

  公开号：US20100278733A1

  公开（公告）日：2010-11-04

  There is provided a composition comprising a compound represented by general formula (I), wherein R l represents a 5-iodothiophen-2-yl group or the like, and R 2 represents a 4-dimethylaminophenyl group or the like. This composition is useful for diagnosis of an amyloid-related disease such as Alzheimer's disease because the compound has high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and a property of being rapidly eliminated from sites other than senile plaques in the brain.

  提供了一种化合物组合物，其由一般式(I)所代表的化合物组成，其中R1代表5-碘噻吩-2-基基团或类似物，R2代表4-二甲氨基苯基基团或类似物。该组合物对于诊断与淀粉样蛋白相关的疾病，如阿尔茨海默病，具有高结合特异性，高透过血脑屏障的渗透性，以及在大脑老年斑以外的部位迅速被排除的特性。
• COMPOSITION FOR DIAGNOSING AMYLOID-RELATED DISEASE
  申请人：Nagasaki University

  公开号：EP2030635A1

  公开（公告）日：2009-03-04

  There is provided a composition comprising a compound represented by general formula (I), wherein R1 represents a 5-iodothiophen-2-yl group or the like, and R2 represents a 4-dimethylaminophenyl group or the like. This composition is useful for diagnosis of an amyloid-related disease such as Alzheimer's disease because the compound has high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and a property of being rapidly eliminated from sites other than senile plaques in the brain.

  提供了一种化合物组合物，其由一般式（I）表示的化合物组成，其中R1代表5-碘噻吩-2-基基团或类似物，R2代表4-二甲氨基苯基团或类似物。该组合物对于诊断与淀粉样蛋白相关的疾病，如阿尔茨海默病，具有高结合特异性，高透过血脑屏障的渗透性，以及在大脑老年斑以外部位迅速被排除的特性。
• Structure–activity relationship of chalcones and related derivatives as ligands for detecting of β-amyloid plaques in the brain
  作者：Masahiro Ono、Miyuki Hori、Mamoru Haratake、Takami Tomiyama、Hiroshi Mori、Morio Nakayama

  DOI：10.1016/j.bmc.2007.06.055

  日期：2007.10

  A series of novel chalcones and their related derivatives were synthesized and evaluated as beta-amyloid imaging probes. In the structure-activity relationship of binding affinities to synthetic A beta(1-42) aggregates, compound 14 displayed the highest binding affinity in vitro. Amyloid plaques in the Alzheimer's model mouse brain were visualized with 14. In biodistribution studies using normal mice, [I-125]14 showed good brain uptake (2.56% ID/g, 2 min postinjection) and rapid washout from the brain (0.21% ID/g, 60 min postinjection). These results suggest that [I-125]14 should be further investigated as a potentially useful P-amyloid imaging probe.