4-[(1E)-3-(5-methylfuran-2-yl)-3-oxoprop-1-en-1-yl]benzoic acid | 1547266-15-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-[(1E)-3-(5-methylfuran-2-yl)-3-oxoprop-1-en-1-yl]benzoic acid
• 英文别名: 4-[(E)-3-(5-methyl-2-furyl)-3-oxo-prop-1-enyl]benzoic acid；4-[(E)-3-(5-methylfuran-2-yl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 1547266-15-8
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: BANYTUALJGETKK-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.51
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-[(1E)-3-(5-methylfuran-2-yl)-3-oxoprop-1-en-1-yl]benzoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis, in vitro antimalarial activity and cytotoxicity of novel 4-aminoquinolinyl-chalcone amides

  摘要：

  A series of 4-aminoquinolinyl-chalcone amides 11-19 were synthesized through condensation of carboxylic acid-functionalized chalcone with aminoquinolines, using 1,1'-carbonyldiimidazole as coupling agent. These compounds were screened against the chloroquine sensitive (3D7) and chloroquine resistant (W2) strains of Plasmodium falciparum. Their cytotoxicity towards the WI-38 cell line of normal human fetal lung fibroblast was determined. All compounds were found active, with IC50 values ranging between 0.04-0.5 mu M and 0.07-1.8 mu M against 3D7 and W2, respectively. They demonstrated moderate to high selective activity towards the parasitic cells in the presence of mammalian cells. However, amide 15, featuring the 1,6-diaminohexane linker, despite possessing predicted unfavourable aqueous solubility and absorption properties, was the most active of all the amides tested. It was found to be as potent as CQ against 3D7, while it displayed a two-fold higher activity than CQ against the W2 strain, with good selective antimalarial activity (SI = 435) towards the parasitic cells. During this study, amide 15 was thus identified as the best drug-candidate to for further investigation as a potential drug in search for new, safe and effective antimalarial drugs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.032
• 作为产物：
  描述：

  5-甲基-2-乙酰基呋喃 、 对醛基苯甲酸 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以90%的产率得到4-[(1E)-3-(5-methylfuran-2-yl)-3-oxoprop-1-en-1-yl]benzoic acid
  参考文献：
  名称：

  Synthesis, in vitro antimalarial activity and cytotoxicity of novel 4-aminoquinolinyl-chalcone amides

  摘要：

  A series of 4-aminoquinolinyl-chalcone amides 11-19 were synthesized through condensation of carboxylic acid-functionalized chalcone with aminoquinolines, using 1,1'-carbonyldiimidazole as coupling agent. These compounds were screened against the chloroquine sensitive (3D7) and chloroquine resistant (W2) strains of Plasmodium falciparum. Their cytotoxicity towards the WI-38 cell line of normal human fetal lung fibroblast was determined. All compounds were found active, with IC50 values ranging between 0.04-0.5 mu M and 0.07-1.8 mu M against 3D7 and W2, respectively. They demonstrated moderate to high selective activity towards the parasitic cells in the presence of mammalian cells. However, amide 15, featuring the 1,6-diaminohexane linker, despite possessing predicted unfavourable aqueous solubility and absorption properties, was the most active of all the amides tested. It was found to be as potent as CQ against 3D7, while it displayed a two-fold higher activity than CQ against the W2 strain, with good selective antimalarial activity (SI = 435) towards the parasitic cells. During this study, amide 15 was thus identified as the best drug-candidate to for further investigation as a potential drug in search for new, safe and effective antimalarial drugs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.032

文献信息

• Synthesis and in vitro biological activities of ferrocenyl–chalcone amides
  作者：Frans J. Smit、Jaco J. Bezuidenhout、Carlos C. Bezuidenhout、David D. N’Da

  DOI：10.1007/s00044-016-1509-y

  日期：2016.4

  revealed that most of the synthesized amides were inactive against all of these microorganisms. Compound 17, however, with an aminodi(ethyleneoxy) linker, displayed moderate bactericidal activity against the gram-negative microorganisms, with a MIC100 value of 128 µM. The outcomes of this study may hence significantly contribute toward malaria and cancer chemotherapy research, and more generally to the

  一系列aminoferrocenyl查耳酮酰胺11 - 19是通过一个羧酸官能化查耳酮的缩合合成10与ferrocenylamines，使用1,1'-羰二咪唑作为偶合剂。筛选了这些化合物对恶性疟原虫CQS 3D7和CQR FCR3菌株的抗血浆活性。发现所有化合物均具有活性，针对3D7和FCR3的IC 50值分别在0.5–4.5和2.1–6.6 µM之间。具有2-氨基乙烯接头的酰胺11是所有化合物中最活跃的，其IC 50分别针对3D7和FCR3菌株的2.6和2.1 µM值。在针对三种癌细胞系（即TK-10，UACC-62和MCF-7）的筛选中，与哌嗪基连接基相比，具有哌嗪基接头的酰胺19对所有三种细胞系的活性均增强。对六种不同微生物进行的抗菌测定表明，大多数合成的酰胺对所有这些微生物均无活性。但是，具有氨基二（亚乙基氧基）接头的化合物17的MIC 100对革兰氏阴性微生物显示中等的杀菌活性值为128
• Synthesis and in vitro biological evaluation of dihydroartemisinyl-chalcone esters
  作者：Frans J. Smit、Riëtte A. van Biljon、Lyn-Marie Birkholtz、David D. N'Da

  DOI：10.1016/j.ejmech.2014.11.016

  日期：2015.1

  A series of dihydroartemisinyl-chalcone esters were synthesized through esterification of chalcones with dihydroartemisinin (DHA). The hybrids were screened against chloroquine (CQ) sensitive (3D7) and CQ resistant (W2) strains of intraerythrocytic Plasmodium falciparum parasites, and were all found to be active, with IC50 values ranging between 1.5 and 11 nM against both strains, with SI values over 5800. The esters featuring oxygenated aryl rings (7,10 and 11), were found to be equipotent to DHA, but were 2-3 times more active than artesunate against the 3D7 and W2 strains of the malaria parasites. They were also screened in vitro against a panel of three cancer cell lines consisting of TK-10, UACC-62 and MCF-7. Compound 7, bearing a furan ring, displayed the most potent overall antitumor activity against all three cancer cell lines. TGA revealed that the targeted hybrids were all thermally more stable than DHA, which may be beneficial to the high temperature storage conditions that prevail in malaria endemic countries. During this study, ester 7 was identified as the best candidate for further investigation as a potential drug in search for new, safe and effective antimalarial drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis, in vitro antimalarial activity and cytotoxicity of novel 4-aminoquinolinyl-chalcone amides
  作者：Frans J. Smit、David D. N’Da

  DOI：10.1016/j.bmc.2013.12.032

  日期：2014.2

  A series of 4-aminoquinolinyl-chalcone amides 11-19 were synthesized through condensation of carboxylic acid-functionalized chalcone with aminoquinolines, using 1,1'-carbonyldiimidazole as coupling agent. These compounds were screened against the chloroquine sensitive (3D7) and chloroquine resistant (W2) strains of Plasmodium falciparum. Their cytotoxicity towards the WI-38 cell line of normal human fetal lung fibroblast was determined. All compounds were found active, with IC50 values ranging between 0.04-0.5 mu M and 0.07-1.8 mu M against 3D7 and W2, respectively. They demonstrated moderate to high selective activity towards the parasitic cells in the presence of mammalian cells. However, amide 15, featuring the 1,6-diaminohexane linker, despite possessing predicted unfavourable aqueous solubility and absorption properties, was the most active of all the amides tested. It was found to be as potent as CQ against 3D7, while it displayed a two-fold higher activity than CQ against the W2 strain, with good selective antimalarial activity (SI = 435) towards the parasitic cells. During this study, amide 15 was thus identified as the best drug-candidate to for further investigation as a potential drug in search for new, safe and effective antimalarial drugs. (C) 2013 Elsevier Ltd. All rights reserved.