1-(4-iodophenyl)-3-(2-thienyl)-prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-iodophenyl)-3-(2-thienyl)-prop-2-en-1-one
• 英文别名: 1-(4-Iodophenyl)-3-(2-thienyl)-2-propen-1-one；(E)-1-(4-iodophenyl)-3-thiophen-2-ylprop-2-en-1-one
• 化学式: C₁₃H₉IOS
• 分子量: 340.184
• InChiKey: AUFXPMODKSMAMW-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-iodophenyl)-3-(2-thienyl)-prop-2-en-1-one 、 二氧化氮 以38%的产率得到
  参考文献：
  名称：

  SITKIN A. I.; KLIMENKO V. I., XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 1, 41-43

  摘要：

  DOI：
• 作为产物：
  描述：

  2-噻吩甲醛 、 4-碘代苯乙酮 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以79.1%的产率得到1-(4-iodophenyl)-3-(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.
• Stilbene–Chalcone Hybrids: Design, Synthesis, and Evaluation as a New Class of Antimalarial Scaffolds That Trigger Cell Death through Stage Specific Apoptosis
  作者：Naina Sharma、Dinesh Mohanakrishnan、Amit Shard、Abhishek Sharma、Saima、Arun K. Sinha、Dinkar Sahal

  DOI：10.1021/jm201216y

  日期：2012.1.12

  Novel stilbene-chalcone (S-C) hybrids were synthesized via a sequential Claisen-Schmidt-Knoevenagel-Heck approach and evaluated for antiplasmodial activity in in vitro red cell culture using SYBR Green I assay. The most potent hybrid (11) showed IC50 of 2.2, 1.4, and 6.4 mu M against 3D7 (chloroquine sensitive), Indo, and Dd2 (chloroquine resistant) strains of Plasmodium falciparum, respectively. Interestingly, the respective individual stilbene (IC50 > 100 mu M), chalcone (IC50 = 11.5 mu M), or an equimolar mixture of stilbene and chalcone (IC50 = 32.5 mu M) were less potent than 11. Studies done using specific stage enriched cultures and parasite in continuous culture indicate that 11 and 18 spare the schizont but block the progression of the parasite life cycle at the ring or the trophozoite stages. Further, 11 and 18 caused chromatin condensation, DNA fragmentation, and loss of mitochondrial membrane potential in Plasmodium falciparum, thereby suggesting their ability to cause apoptosis in malaria parasite.
• SITKIN A. I.; KLIMENKO V. I., XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 1, 41-43
  作者：SITKIN A. I.、 KLIMENKO V. I.

  DOI：——

  日期：——