1-(furan-2-yl)-3-(4-hydroxyphenyl)-2-propen-1-one | 209392-27-8

• 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: 1-(furan-2-yl)-3-(4-hydroxyphenyl)-2-propen-1-one
• 英文别名: 1-(furan-2-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 209392-27-8
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: POPCGDXTXGSDLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(furan-2-yl)-3-(4-hydroxyphenyl)-2-propen-1-one 在 hydrazine hydrate 、 potassium carbonate 、 溶剂黄146 作用下， 反应 0.36h， 生成 6-(furan-2-yl)-4-(4-hydroxyphenyl)-4,5-dihydro-2H-indazol-3-ol
  参考文献：
  名称：

  Mechanochemical synthesis of cyclohexenones and indazoles as potential antimicrobial agents

  摘要：

  利用球磨产生的机械力高效、定量地制备了一系列环己烯酮和吲唑。该方法环保、简便、时间短且无溶剂。根据单晶 X 射线衍射，获得的环己烯酮的结构分配非常明确。利用傅立叶变换红外光谱、氢和碳核磁共振（NMR）光谱、同核相关光谱、无畸变极化传递增强（DEPT）NMR 和气相色谱-质谱法对吲唑类化合物的结构进行了表征。对合成的化合物进行了抗菌活性筛选，以检测其对两种革兰氏阳性菌（耐甲氧西林金黄色葡萄球菌和黄体微球菌）、三种革兰氏阴性菌（克雷伯菌、鼠伤寒沙门氏菌和宋内志贺氏菌）以及三种真菌（白色念珠菌、黑曲霉和黄曲霉）的抗菌活性。评估了不同取代基对合成化合物抗菌和抗真菌活性的影响。在 4 位上带有噻吩分子的环己酮衍生物显示出与抗生素四环素相当的抗菌活性。

  DOI：

  10.1007/s11164-015-2379-5
• 作为产物：
  描述：

  4-(四氢-吡喃-2-基氧基)-苯甲醛 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 1-(furan-2-yl)-3-(4-hydroxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent

  摘要：

  In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-gamma/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r (2) = 0.989 and a good cross validated value, q (2) = 0.583.

  DOI：

  10.1007/s00044-011-9706-1

文献信息

• In vitro and in vivo synergistic interaction of substituted chalcone derivatives with norfloxacin against methicillin resistant Staphylococcus aureus
  作者：Rashmi Gaur、Vivek Kumar Gupta、Anirban Pal、Mahendra Padurang Darokar、Rajendra Singh Bhakuni、Brijesh Kumar

  DOI：10.1039/c4ra10842f

  日期：——

  Thirty chalcone derivatives were synthesized via a base catalyzed Claisen Schmidt condensation and evaluated for their anti-methicillin-resistant Staphylococcus aureus (MRSA) activity alone and in combination with norfloxacin. Among these, 5 derivatives namely trans-3-(1H-indol-3-yl)-1-(4′-benzyloxyphenyl)-2-propen-1-one (2), 1-(4″-biphenyl)-3-(3′4′-dihydroxyphenyl)-2-propen-1-one (11), 1-(4″-hydroxy-3

  通过碱催化的克莱森·施密特缩合反应合成了三十种查尔酮衍生物，并单独或与诺氟沙星组合评估了它们的抗甲氧西林抗金黄色葡萄球菌（MRSA）活性。其中5个衍生物，即反式-3-（1 H-吲哚-3-基）-1-（4'-苄氧基苯基）-2-丙烯-1-酮（2），1-（4″-联苯）- 3-（3'4'-二羟基苯基）-2-丙烯-1-酮（11），1-（4''-羟基-3''-甲基苯基）3-（4'-羟基苯基）-2-丙烯-1-一（14），3-（4'-氯苯基）-1-（4''-羟苯基）2-丙烯-1-酮（17）和LTG-肟（27）在MIC 12.5–50 µg时显示出显着的抗菌活性。毫升-1。在组合研究中，衍生物2和14显著诺氟沙星高达16倍（FICI <0.5）降低了MIC，而衍生物11， 17和27减少了它由多达八个倍（FICI≤0.5）。流式细胞仪分析结果清楚地表明，衍生物2和14显着促进了Et-Br外排的积累和抑制，这通
• Thieny/Furanyl-hydroxyphenylpropenones as Inhibitors of LPS-induced ROS and NO Production in RAW 264.7 Macrophages, and Their Structure-Activity Relationship Study
  作者：Tara Man Kadayat、Mi Jin Kim、Tae-Gyu Nam、Pil-Hoon Park、Eung-Seok Lee

  DOI：10.5012/bkcs.2014.35.8.2481

  日期：2014.8.20

  Twelve thienyl/furanyl-hydroxyphenylpropenones were systematically designed and synthesized, and evaluated for their inhibitory effect on LPS-induced ROS and NO production in RAW 264.7 macrophages. Compound 11 displayed the most significant inhibitory activity of LPS-induced ROS and NO production in RAW 264.7 macrophages. Structure-activity relationship study indicated that para-hydroxyphenyl moiety plays an important role for inhibitory activities on both LPS-induced ROS and NO production as well as 3-thienyl moiety on molecule.

  系统设计并合成了十二种噻吩/呋喃羟基苯丙烯酮，并评估其对LPS诱导的RAW 264.7巨噬细胞中ROS和NO产生的抑制作用。化合物11在抑制LPS诱导的RAW 264.7巨噬细胞中ROS和NO产生方面表现出最显著的抑制活性。结构-活性关系研究表明，para-羟基苯基部分在抑制LPS诱导的ROS和NO产生方面起着重要作用，而分子中的3-噻吩部分也同样关键。
• Synthesis and Evaluation of Chalcone Derivatives as Inhibitors of Neutrophils' Chemotaxis, Phagocytosis and Production of Reactive Oxygen Species
  作者：Syed N. A. Bukhari、Yasmin Tajuddin、Vannessa J. Benedict、Kok W. Lam、Ibrahim Jantan、Juriyati Jalil、Malina Jasamai

  DOI：10.1111/cbdd.12226

  日期：2014.2

  Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti‐inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol‐ and lucigenin‐based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4‐methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators.
• Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent
  作者：Kok Wai Lam、Reaz Uddin、Choi Yi Liew、Chau Ling Tham、Daud A. Israf、Ahmad Syahida、Mohd. Basyaruddin Abdul Rahman、Zaheer Ul-Haq、Nordin H. Lajis

  DOI：10.1007/s00044-011-9706-1

  日期：2012.8

  In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-gamma/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r (2) = 0.989 and a good cross validated value, q (2) = 0.583.
• Mechanochemical synthesis of cyclohexenones and indazoles as potential antimicrobial agents
  作者：Abdullah S. Al-Bogami

  DOI：10.1007/s11164-015-2379-5

  日期：2016.6

  Mechanical force from ball milling was used for efficient and quantitative preparation of a series of cyclohexenones and indazoles. The method is environmentally friendly, simple, short, and solventless. Unambiguous structural assignments of the obtained cyclohexenones were achieved based on single-crystal X-ray diffraction. The structures of the indazoles were characterized using Fourier-transform infrared spectroscopy, hydrogen and carbon nuclear magnetic resonance (NMR) spectroscopy, homonuclear correlation spectroscopy, distortionless enhancement by polarization transfer (DEPT) NMR, and gas chromatography–mass spectrometry. The synthesized compounds were screened for antimicrobial activity against two Gram-positive bacteria (methicillin-resistant staphylococcus aureus and Micrococcus luteus), three Gram-negative bacteria (Klebsiella oxytoca, Salmonella typhimurium, and Shigella sonnei), and three fungi (Candida albicans, Aspergillus niger, and A. flavus). The effects that different substituents on the synthesized compounds had on the antibacterial and antifungal activities were evaluated. Cyclohexenone derivatives with thiophene moiety at 4-position showed antibacterial activity comparable to the antibiotic tetracycline.

  利用球磨产生的机械力高效、定量地制备了一系列环己烯酮和吲唑。该方法环保、简便、时间短且无溶剂。根据单晶 X 射线衍射，获得的环己烯酮的结构分配非常明确。利用傅立叶变换红外光谱、氢和碳核磁共振（NMR）光谱、同核相关光谱、无畸变极化传递增强（DEPT）NMR 和气相色谱-质谱法对吲唑类化合物的结构进行了表征。对合成的化合物进行了抗菌活性筛选，以检测其对两种革兰氏阳性菌（耐甲氧西林金黄色葡萄球菌和黄体微球菌）、三种革兰氏阴性菌（克雷伯菌、鼠伤寒沙门氏菌和宋内志贺氏菌）以及三种真菌（白色念珠菌、黑曲霉和黄曲霉）的抗菌活性。评估了不同取代基对合成化合物抗菌和抗真菌活性的影响。在 4 位上带有噻吩分子的环己酮衍生物显示出与抗生素四环素相当的抗菌活性。